77 results on '"Jean Weiss"'
Search Results
2. Tetra-(benzo-24-crown-8)-phthalocyanines as a platform for supramolecular ensembles: Synthesis and interaction with viologen
- Author
-
Yulia G. Gorbunova, Vadim V. Minin, Elena A. Ugolkova, Aslan Yu. Tsivadze, Nikolay N. Efimov, Jean Weiss, Evgeniya A. Safonova, Jennifer A. Wytko, A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences [Moscow] (RAS), Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and N. S. Kurnakov Institute of General and Inorganic Chemistry (IGIC)
- Subjects
chemistry.chemical_classification ,biology ,010405 organic chemistry ,Ligand ,Supramolecular chemistry ,Viologen ,General Chemistry ,010402 general chemistry ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,law.invention ,Supramolecular assembly ,chemistry.chemical_compound ,chemistry ,law ,Polymer chemistry ,medicine ,Phthalocyanine ,Tetra ,[CHIM.COOR]Chemical Sciences/Coordination chemistry ,Electron paramagnetic resonance ,Crown ether ,medicine.drug - Abstract
The synthesis of a series of novel tetra-(benzo-24-crown-8)-phthalocyanines (Mg(II), Ni(II) and Co(II)) as well as a modified procedure for the free-base ligand and its Zn(II) and Cu(II) complexes are reported. The tendency of these phthalocyanines to undergo supramolecular cofacial dimerization induced by interaction with a viologen ([Formula: see text]-di(but-3-ynyl)-4,4[Formula: see text]-bipyridinium) was investigated by UV-vis absorption and EPR spectral studies in solution. The nature of the metal cation in phthalocyanine, the concentration, as well as the solvent all influenced the assembly processes.
- Published
- 2020
3. Single-Molecule Junctions with Highly Improved Stability
- Author
-
Maïwenn Combes, Maxime Vonesch, Xinlei Yao, Xiaonan Sun, Jean Weiss, and Jean-Christophe Lacroix
- Subjects
Materials science ,chemistry.chemical_element ,Bioengineering ,02 engineering and technology ,010402 general chemistry ,01 natural sciences ,law.invention ,chemistry.chemical_compound ,law ,Molecule ,General Materials Science ,Mechanical Engineering ,Conductance ,Free base ,General Chemistry ,021001 nanoscience & nanotechnology ,Condensed Matter Physics ,Porphyrin ,0104 chemical sciences ,Crystallography ,chemistry ,Covalent bond ,Scanning tunneling microscope ,0210 nano-technology ,Break junction ,Cobalt - Abstract
Single-molecule junctions (SMJs) have been fabricated using layers generated by diazonium electroreduction. This process creates a C-Au covalent bond between the molecule and the electrode. Rigid oligomers of variable length, based on porphyrin derivatives in their free base or cobalt complex forms, have been grafted on the surface. The conductance of the oligomers has been studied by a scanning tunneling microscopy break junction (STM-bj) technique and G(t) measurements, and the lifetime of the SMJs has been investigated. The conductance histograms indicate that charge transport in the porphyrins is relatively efficient and influenced by the presence of the cobalt center. With both systems, random telegraph G(t) signals are easily recorded, showing SMJ on/off states. The SMJs then stabilize and exhibit a surprisingly long lifetime around 10 s, and attenuation plots, obtained by both G(t) and STM-bj measurements, give identical values. This work shows that highly stable SMJs can be prepared using a diazonium grafting approach.
- Published
- 2021
4. Porphyrins and Polyoxometalate Scaffolds
- Author
-
Raphaël Lamare, Jean Weiss, Romain Ruppert, Corinne Boudon, and Laurent Ruhlmann
- Subjects
Porphyrins ,Organic Chemistry ,Nanotechnology ,Context (language use) ,General Chemistry ,Chromophore ,Tungsten Compounds ,Porphyrin ,Catalysis ,Electron Transport ,chemistry.chemical_compound ,chemistry ,Polyoxometalate ,Hybrid material - Abstract
Polyoxometalates (POMs) can act as unique reservoirs for multiple electron transfers. As POMs display only weak absorption in the visible spectrum, they can be associated with chromophores such as porphyrins and porphyrin antennae. In this Minireview, the research dedicated to the combination of porphyrins and polyoxometalates is put in context and the state of the art identifying the challenges addressed in the optimization of hybrid materials for applications is detailed.
- Published
- 2021
5. ORR activity of metalated phenanthroline-strapped porphyrin adsorbed on carbon nanotubes
- Author
-
Jean Weiss, Renaud Cornut, Bruno Jousselme, Stéphane Campidelli, Jennifer A. Wytko, Manel Hanana, Christophe Kahlfuss, CEA, Université Paris-Saclay (CEA), Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR-16-CE29-0027,MAGMA,Propriétés Magnétiques du Graphène Fonctionnalisé par des Assemblages Moléculaires Bidimensionnels(2016), and Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
Oxygen reduction ,Phenanthroline ,Carbon nanotubes ,Carbon nanotube ,Électrocatalyse ,[CHIM.INOR]Chemical Sciences/Inorganic chemistry ,010402 general chemistry ,01 natural sciences ,law.invention ,Porphyrin ,chemistry.chemical_compound ,Adsorption ,law ,Porphyrine ,Polymer chemistry ,[CHIM]Chemical Sciences ,Electrical and Electronic Engineering ,Nanotubes de carbone ,Energy ,010405 organic chemistry ,Réduction de l'oxygène ,Building and Construction ,0104 chemical sciences ,chemistry ,Énergie ,Electrocatalysis - Abstract
International audience; Developing efficient noble metal-free systems for electrocatalysis and the reduction of oxygen (ORR) is crucial for hydrogen economy. Bioinspired hybrids combining iron or copper/iron porphyrins with multiwalled carbon nanotubes were tested for ORR using a rotating ring-disk electrode at pH 13 to 8. The porphyrin-nanotube hybrids exhibited better electrocatalytic properties than their constituents alone due to the electrical network formed by the nanotubes, and they reduced oxygen via a four-electron pathway to produce water. Whereas the presence of Cu was not mandatory to reduce oxygen, its presence improved ORR activity and decreased the overpotential compared to monometalic (iron porphyrin) hybrids.; La conception de matériaux sans métaux nobles pour la réaction de réduction de l'oxygène (ORR) est cruciale pour le développement d'une économie basée sur l'hydrogène. Ici, des matériaux hybrides bioinspirés à base de porphyrines métallées et de nanotubes de carbone multi-parois ont été testés pour l'ORR avec un système d'électrode disque-anneau entre pH 8 et 13. Les matériaux hybrides présentent systématiquement de meilleures propriétés électrocatalytiques que celles de leurs constituants pris individuellement et permettent de réduire l'oxygène par un processus à quatre électrons. La présence du cuivre dans les hybrides n'est pas obligatoire mais elle améliore légèrement les propriétés électrocatalytiques.
- Published
- 2021
6. Hydrogen bond directed molecular recognition in water in a strapped-porphyrin-cyclodextrin assembly
- Author
-
Hiroaki Kitagishi, Jennifer A. Wytko, Maxime Vonesch, Kazuki Ohara, Jean Weiss, Daiki Shimoji, Doshisha University [Kyoto], Institut de Chimie de Strasbourg, and Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
chemistry.chemical_classification ,Aqueous medium ,Cyclodextrin ,010405 organic chemistry ,Hydrogen bond ,General Chemistry ,hydrogen bonding ,010402 general chemistry ,01 natural sciences ,Porphyrin ,0104 chemical sciences ,b-cyclodextrin ,Zinc porphyrin ,porphyrin ,chemistry.chemical_compound ,Water soluble ,Molecular recognition ,chemistry ,host–guest complex ,Polymer chemistry ,aqueous medium ,[CHIM.COOR]Chemical Sciences/Coordination chemistry - Abstract
A water soluble, phenanthroline-strapped zinc porphyrin bearing four arylsulfonate groups formed a stable host–guest complex with two per-[Formula: see text]-methylated [Formula: see text]-cyclodextrin cavities. In the host–guest assembly, the zinc porphyrin was capable of binding imidazole within the cavity between the zinc(II) ion and the phenanthroline strap in an aqueous medium. The formation of a hydrogen bond between the imidazole NH and the nitrogen atoms of the phenanthroline was an essential element of the binding event, as shown by comparative binding studies with a non-strapped tetrasulfonated zinc porphyrin and with [Formula: see text]-methylimidazole. This hydrogen bonding in an aqueous medium was possible due to the protected hydrophobic environment created by the cyclodextrins around the phenanthroline strap. This type of binding event may provide a biomimetic approach to study water soluble heme protein models.
- Published
- 2019
7. Functionalized 4,4′-Bipyridines: Synthesis and 2D Organization on Highly Oriented Pyrolytic Graphite
- Author
-
Jean Weiss, Artur Ciesielski, Jennifer A. Wytko, Jean Joseph, Victor Mamane, Can Wang, Jimmy Richard, and Paolo Samorì
- Subjects
chemistry.chemical_classification ,010405 organic chemistry ,Organic Chemistry ,Supramolecular chemistry ,010402 general chemistry ,01 natural sciences ,Combinatorial chemistry ,0104 chemical sciences ,law.invention ,Bipyridine ,chemistry.chemical_compound ,Highly oriented pyrolytic graphite ,chemistry ,law ,Monolayer ,Scanning tunneling microscope ,Linker ,Alkyl - Abstract
Commercial 4,4'-bipyridine is a popular scaffold that is primarily employed as a linker in 3D self-assembled architectures such as metallo-organic frameworks or as a connector in 2D networks. The introduction of alkyl substituents on the bipyridine skeleton is instrumental when 4,4'-bipyridines are used as linkers to form 2D self-assembled patterns on surfaces. Here, several synthetic strategies to access 4,4'-bipyridines functionalized at various positions are described. These easily scalable reactions have been used to introduce a range of alkyl substituents at positions 2 and 2' or 3 and 3' and at positions 2,2' and 6,6' in the case of tetra-functionalization. Scanning tunneling microscopy studies of molecular monolayers physisorbed at the graphite-solution interface revealed different supramolecular patterns whose motifs are primarily dictated by the nature and position of the alkyl chains.
- Published
- 2021
- Full Text
- View/download PDF
8. A New Phenanthroline Ligand and the Spontaneous Resolution of its Homoleptic Copper(I) Complex
- Author
-
Vincent Silber, Jean-Claude Chambron, Lydia Karmazin, Romain Ruppert, Jordan L. Appleton, Jean Weiss, Corinne Bailly, Institut de Chimie de Strasbourg, and Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
010405 organic chemistry ,Ligand ,Phenanthroline ,Organic Chemistry ,Resolution (electron density) ,chemistry.chemical_element ,010402 general chemistry ,01 natural sciences ,Copper ,0104 chemical sciences ,chemistry.chemical_compound ,Crystallography ,chemistry ,[CHIM]Chemical Sciences ,Physical and Theoretical Chemistry ,Homoleptic ,ComputingMilieux_MISCELLANEOUS - Abstract
International audience
- Published
- 2020
9. Probing the Growth of Organic Molecular Films Embedded between Cobalt and Iron Electrodes: Ferromagnetic Nuclear Resonance Approach
- Author
-
Christian Meny, Jacek Arabski, Jean Weiss, Garen Avedissian, Jennifer A. Wytko, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Institut de Chimie de Strasbourg, Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and univOAK, Archive ouverte
- Subjects
Materials science ,Nanostructure ,Supramolecular chemistry ,Aucun ,chemistry.chemical_element ,02 engineering and technology ,010402 general chemistry ,01 natural sciences ,Biomaterials ,chemistry.chemical_compound ,Molecular film ,Monolayer ,Electrochemistry ,[CHIM.MATE] Chemical Sciences/Material chemistry ,[CHIM.MATE]Chemical Sciences/Material chemistry ,021001 nanoscience & nanotechnology ,Condensed Matter Physics ,Porphyrin ,0104 chemical sciences ,Electronic, Optical and Magnetic Materials ,Solid-state nuclear magnetic resonance ,Ferromagnetism ,chemistry ,Chemical physics ,0210 nano-technology ,Cobalt - Abstract
Physical properties of magnetic nanostructures and devices strongly depend on the morphological characteristics of their various components. This is especially true and becomes particularly complex in hybrid nanostructures, where soft organic molecules are at the vicinity of ferromagnetic metallic films. The supramolecular architecture of molecular films embedded between iron (Fe) and cobalt (Co) layers, has been investigated by ferromagnetic nuclear resonance (FNR). In such sample architecture, the presence of pin holes in the organic layers is detected by FNR contributions in a specific spectral range. The methodology that has been developed allows probing the continuity and packing of zinc tetra-phenyl porphyrin (ZnTPP) molecular films between the Co and Fe films. The experimental results suggest that, regardless of the nature of the ferromagnetic under-layer, at least 15 monolayers of ZnTPP are necessary to form continuous and pin-hole free molecular films. In addition, quantitative analyses show that ZnTPP layers exhibit distinct morphologies that are dependent on the nature of the ferromagnetic metallic under-layer.
- Published
- 2020
10. Case studies of the radical cation reactivity in meso-aryl and octaethyl porphyrins
- Author
-
Raphaël Lamare, Romain Ruppert, Jean Weiss, Laurent Ruhlmann, Institut de Chimie de Strasbourg, Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), Laboratoire de Chimie Quantique, Centre National de la Recherche Scientifique (CNRS), and Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
Access route ,010405 organic chemistry ,Chemistry ,Aryl ,Cationic polymerization ,General Chemistry ,010402 general chemistry ,01 natural sciences ,Porphyrin ,Medicinal chemistry ,0104 chemical sciences ,3. Good health ,chemistry.chemical_compound ,Radical ion ,Nucleophile ,Reactivity (chemistry) ,[CHIM.OTHE]Chemical Sciences/Other - Abstract
The reactivity of porphyrin radical cationic species derived from octaethyl porphyrin (OEP) or meso-aryl porphyrins with nucleophiles, envisioned as an access route to elaborate porphyrin dimers, has been studied and optimized in the case of OEP. Standardized conditions have been applied to various spacers to show that the success of the reaction is mostly nucleophile dependent and that the method has little chances to yield non-linear bis-porphyrins.
- Published
- 2019
11. Modelling haemoproteins: Porphyrins and cyclodextrins as sources of inspiration
- Author
-
Hiroaki Kitagishi, Jennifer A. Wytko, Maxime Vonesch, Koji Kano, Jean Weiss, Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Doshisha University [Kyoto], and Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC)
- Subjects
Hemeproteins ,Models, Molecular ,Porphyrins ,010402 general chemistry ,Ligands ,01 natural sciences ,Catalysis ,chemistry.chemical_compound ,Cucurbituril ,Materials Chemistry ,Molecule ,[CHIM]Chemical Sciences ,Reactivity (chemistry) ,[CHIM.COOR]Chemical Sciences/Coordination chemistry ,Solubility ,Cyclodextrins ,Molecular Structure ,010405 organic chemistry ,Ligand ,Chemistry ,Metals and Alloys ,Cavitand ,Water ,General Chemistry ,Combinatorial chemistry ,Porphyrin ,0104 chemical sciences ,Surfaces, Coatings and Films ,Electronic, Optical and Magnetic Materials ,Covalent bond ,Ceramics and Composites ,Hydrophobic and Hydrophilic Interactions - Abstract
International audience; The association of hydrophobic cavities with porphyrin derivatives has been used to mimic haemoproteinstructures. The most employed cavity in this field is b-cyclodextrin (b-CD) and scaffolds combining beta-CDs and porphyrinsare expected to inspire the combination of porphyrins and cucurbiturils in a near future. Aside from providing watersolubility to various porphyrinic structures, the beta-CD framework can also modulate and control the reactivity of the metalcore of the porphyrin. After a general introduction of the challenges faced in the field of haemoprotein models and thebinding behavior of beta-CDs, the article will discuss covalent and non-covalent association of porphyrins with beta-CDs. In eachapproach, the role of the CD differs according to the relative position of the concave CD host, either directly controlling thebinding and transformation of a substrate on the metalloporphyrin or playing a dual role of controlling the water solubilityand selecting the axial ligand of the metal core. The discussion will be of interest to the cucurbituril community as well asto the cavitand community as the information provided should be useful for the design of haemoprotein mimics usingcucurbiturils (CBs).
- Published
- 2019
12. Mononuclear oxovanadium(IV) Schiff base complex: Synthesis, spectroscopy, electrochemistry, DFT calculation and catalytic activity
- Author
-
Jean Weiss, Douniazed Hannachi, Sabrina Bendia, Kamel Ouari, and Souad Dekar
- Subjects
Schiff base ,010405 organic chemistry ,Chemistry ,Ligand ,Organic Chemistry ,Cyclohexene ,Infrared spectroscopy ,Vanadium ,chemistry.chemical_element ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Redox ,0104 chemical sciences ,Catalysis ,Inorganic Chemistry ,chemistry.chemical_compound ,Materials Chemistry ,Physical chemistry ,Physical and Theoretical Chemistry ,Cyclic voltammetry - Abstract
A new complex of oxovanadium, VOL has been synthesized from Schiff base ligand obtained by the condensation of o-phenylenediamine and 5-bromo-salicylaldehyde. All new compounds have been characterized by 1H NMR, IR spectra, UV–Vis spectroscopy, elemental analysis and mass spectrometry. The molar conductance data revealed that the metal complex is a non-electrolyte. Thermal analysis techniques (TGA/DTA) of the ligand and the complex were performed. The proposed structures for the free ligand and the corresponding vanadium complex were corroborated by the use of geometry optimization and conformational analysis. The solid state structure of complex VOL was fully determined by single crystal X-ray diffraction analysis. Similar electrochemical behavior for both the ligand and the corresponding complex have been observed by cyclic voltammetry (CV). The complex gave a metal-based one-electron quasi-reversible redox couple at 606 mV/SCE corresponding to the VOIV/VOV redox process which was consistent with the hydrodynamic voltammograms. Additional peaks in the CVs that were growing with the scan rate have been attributed to consecutive one-electron reduction of the ligand. The catalytic activity of the oxovanadium Schiff base complex VOL was tested in the oxidation reaction of cyclohexene. The efficiency of the catalyst was influenced by the nature of the oxidant. The results showed that the complex was highly active and selective for cyclohexenone in optimized conditions.
- Published
- 2018
13. Metal-mediated linear self-assembly of porphyrins
- Author
-
Romain Ruppert, Jennifer A. Wytko, Christophe Jeandon, Jean Weiss, Institut de Chimie de Strasbourg, Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), and Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
Materials science ,Charge separation ,Nanotechnology ,Electronic structure ,010402 general chemistry ,01 natural sciences ,Catalysis ,Metal ,chemistry.chemical_compound ,Materials Chemistry ,[CHIM.COOR]Chemical Sciences/Coordination chemistry ,Well-defined ,Electronic properties ,010405 organic chemistry ,Metals and Alloys ,General Chemistry ,Porphyrin ,0104 chemical sciences ,Surfaces, Coatings and Films ,Electronic, Optical and Magnetic Materials ,chemistry ,Covalent bond ,visual_art ,Ceramics and Composites ,visual_art.visual_art_medium ,Self-assembly - Abstract
Porphyrin derivatives are highly relevant to biological processes such as light harvesting and charge separation. Their aromatic electronic structure and their accessible HOMO−LUMO gap render porphyrins highly attractive for the development of opto- and electro-active materials. Due to the often difficult covalent synthesis of multiporphyrins, self-assembly using metal complexation as the driving force can lead to well defined objects exhibiting a controlled morphology, which will be required to analyse and understand the electronic properties of porphyrin wires. This article presents two assembly approaches, namely by peripheral coordination or by binding to a metal ion in the porphyrin core, that are efficient and well designed for future developments requiring interactions with a surface.
- Published
- 2018
14. A question of flexibility in cytochrome c oxidase models
- Author
-
Mourad Elhabiri, Petra Hellwig, Pauline Vorburger, Nesrine Oueslati, Corinne Boudon, Mamadou Lo, Sylvie Choua, Maxime Bernard, Frederic Melin, Jennifer A. Wytko, and Jean Weiss
- Subjects
Cytochrome ,biology ,010405 organic chemistry ,Stereochemistry ,Ligand ,Inorganic chemistry ,010402 general chemistry ,01 natural sciences ,Porphyrin ,0104 chemical sciences ,Inorganic Chemistry ,chemistry.chemical_compound ,chemistry ,Materials Chemistry ,biology.protein ,Cytochrome c oxidase ,Carbon monoxide binding ,Physical and Theoretical Chemistry ,Binding site ,Heme ,Oxygen binding - Abstract
The structure-property relationships were compared for the iron and iron-copper complexes of two functional cytochrome c oxidase models, 1 and 2 , both constructed upon a phenanthroline-strapped porphyrin bearing respectively pyridyl or picolinyl built-in proximal and distal ligands. The behavior of these heme models in the absence and in the presence of copper was studied by 1 H NMR, UV–visible absorption, EPR, Raman and FTIR spectroscopies, electrochemistry in solution and deposited on a rotating ring-disk graphite electrode. The distal binding site within the phenanthroline pocket of both 1 and 2 is available for the coordination of exogenic ligands, yet the oxygen binding affinity is higher for all complexes of 2 than for 1 . Despite this difference, [ 1Fe II Cu I ] more efficiently reproduced the electrocatalyzed reduction of oxygen to water than [ 2Fe II Cu I ]. The oxygenated complexes of both iron(II)-copper(I) species mimic the ability of cytochrome c oxidase to reversibly bind O 2 , as shown by competitive binding studies in the presence of CO. Differences in the binding and electrocatalytic properties of these models stem from difference in rigidity of scaffolds upon binding of both the proximal and distal ligands, as well as from the bulkiness of the distal ligand.
- Published
- 2017
15. Structural investigation of the catalytic activity of Fe(III) and Mn(III) Schiff base complexes
- Author
-
Riadh Bourzami, Kamel Ouari, Jean Weiss, and Sabrina Bendia
- Subjects
Schiff base ,010405 organic chemistry ,Ligand ,Cyclohexene ,chemistry.chemical_element ,Manganese ,010402 general chemistry ,01 natural sciences ,Redox ,0104 chemical sciences ,Catalysis ,Inorganic Chemistry ,chemistry.chemical_compound ,Electron transfer ,Crystallography ,chemistry ,Materials Chemistry ,Physical and Theoretical Chemistry ,Cyclic voltammetry - Abstract
Two novel manganese (III) and iron (III) complexes of an N,N-bis(1-naphthalidimine)-o phenylene diamine ligand have been successfully synthesized and characterized by various analytical techniques including single crystal X-ray structure analysis. The ligand crystallizes in the monoclinic system with space group P21/c. The detailed analyses of Hirschfeld surface and fingerprint plots provide insight into the nature of non-covalent interactions in the ligand. Experimental data have been complemented and interpreted in the light of Density Functional Theory calculation was performed using the B3LYP method concerning molecular geometries, vibrational frequencies and electrochemical potentials. Cyclic voltammetry in dimethylformamide revealed reversible redox processes in both complexes, suggesting possible catalytic reactivity involving electron transfer process for these complexes. The catalytic efficiency and selectivity of manganese (III) and iron (III) complexes was tested in the oxidation of cyclohexene with molecular oxygen. The results show that the catalytic performance depends on the nature of metal, the most efficient catalyst in the presence of O2beingthe iron (III) complex. A plausible mechanism for cyclohexene oxidation by complexes is proposed and discussed hereafter.
- Published
- 2021
16. CuAAC in a Distal Pocket: Metal Active-Template Synthesis of Strapped-Porphyrin [2]Rotaxanes
- Author
-
Takashi Hayashi, Yuta Miyazaki, Koji Oohora, Jean Weiss, Takashi Matsumoto, Jennifer A. Wytko, Christophe Kahlfuss, Ayumu Ogawa, and Wytko, Jennifer
- Subjects
Rotaxane ,Tandem ,010405 organic chemistry ,Phenanthroline ,Organic Chemistry ,chemistry.chemical_element ,General Chemistry ,010402 general chemistry ,Photochemistry ,01 natural sciences ,Porphyrin ,Copper ,Catalysis ,Cycloaddition ,0104 chemical sciences ,Metal ,chemistry.chemical_compound ,chemistry ,visual_art ,[CHIM] Chemical Sciences ,Polymer chemistry ,visual_art.visual_art_medium ,Click chemistry - Abstract
The synthesis of a porphyrin rotaxane by dipolar cycloaddition takes advantage of the ditopic character of a phenanthroline-strapped porphyrin. The success of the click reaction was conditioned by the presence of both a coordinatively unsaturated metal in the porphyrin and a copper(I) bound to the phenanthroline, pointing at a new “tandem active metal template” mechanism.
- Published
- 2017
17. From Models of Hemoproteins to Self-Assembled Molecular Wires
- Author
-
Jennifer A. Wytko, Christophe Kahlfuss, Jean Weiss, Chimie de la matière complexe (CMC), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Strasbourg, Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), and Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
Molecular wire ,chemistry.chemical_compound ,chemistry ,010405 organic chemistry ,Nanotechnology ,General Chemistry ,[CHIM.OTHE]Chemical Sciences/Other ,010402 general chemistry ,01 natural sciences ,Porphyrin ,0104 chemical sciences ,Self assembled ,Polyvalence - Abstract
In Nature, the various properties of tetrapyrrolic macrocycles are mostly due to their proteic environment and result from an evolutionary process difficult to reproduce in the lifetime of a synthetic chemist. Thus, the task of synthetic chemists attempting to reproduce the biological role of porphyrin architectures performing functions from catalysis to light harvesting is significantly complicated. This account describes how a phenanthroline-strapped porphyrin architecture initially designed to afford new hemoprotein models led, over the last two decades, to the preparation of highly linear self-assembled nano-objects inspired by light-harvesting architectures. The approach summarized in the next pages mimics, in a very modest way, the polyvalence of tetrapyrrolic macrocycles in Nature.
- Published
- 2017
18. Light triggers molecular shuttling in rotaxanes: control over proximity and charge recombination
- Author
-
Dirk M. Guldi, Jean Weiss, Koji Oohora, Maxime Vonesch, Stéphane Campidelli, Jennifer A. Wytko, Ayumu Ogawa, Mareike Bechtold, Takashi Hayashi, Maximilian Wolf, Inorganic Chemistry, Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM) (ICMM), Friedrich-Alexander Universität Erlangen-Nürnberg (FAU), Division of Applied Chemistry, Graduate School of Engineering, Osaka University, Osaka University [Osaka], Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Karlsruhe Institute of Technology (KIT), Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN UMR 3685), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), JSPS KAKENHI (Grant Number JP15H05804 in Innovative Areas 'Precisely Designed Catalysts with Customized Scaffolding'), Deutsche Forschungsgemeinschat DFG (SFB953 Synthetic Carbon Allotropes), the State of Bavaria (SolTech), ANR-14-JTIC-0002,MECANO,Ingenierie moléculaire et assemblages contrôlés de nanoobjets fonctionnels à base de porphyrines(2014), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut Rayonnement Matière de Saclay (IRAMIS), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
Fullerene ,Materials science ,Chemistry & allied sciences ,010402 general chemistry ,Photochemistry ,01 natural sciences ,chemistry.chemical_compound ,Ultrafast laser spectroscopy ,polycyclic compounds ,Physics::Atomic and Molecular Clusters ,Directionality ,[CHIM.COOR]Chemical Sciences/Coordination chemistry ,Physics::Biological Physics ,[PHYS.PHYS.PHYS-OPTICS]Physics [physics]/Physics [physics]/Optics [physics.optics] ,010405 organic chemistry ,Charge (physics) ,General Chemistry ,Porphyrin ,0104 chemical sciences ,Condensed Matter::Soft Condensed Matter ,Zinc porphyrin ,Solvent ,Chemistry ,chemistry ,ddc:540 ,[PHYS.PHYS.PHYS-CHEM-PH]Physics [physics]/Physics [physics]/Chemical Physics [physics.chem-ph] ,Recombination - Abstract
The lifetime of a charge separated state is enhanced by the effects of solvent polarity and the coordination controlled shuttling of a dumbbell in a porphyrin/fullerene rotaxane., We present the synthesis of novel rotaxanes based on mechanically interlocked porphyrins and fullerene and their advanced investigations by means of photophysical measurements. To this end, a fullerene-capped dumbbell-type axle containing a central triazole was threaded through strapped (metallo)porphyrins—either a free-base or a zinc porphyrin. Femtosecond-resolved transient absorption measurements revealed charge-separation between the porphyrin and fullerene upon light excitation. Solvent polarity and solvent coordination effects induced molecular motion of the rotaxanes upon charge separation and enabled, for the first time, subtle control over the charge recombination by enabling and controlling the directionality of shuttling.
- Published
- 2019
- Full Text
- View/download PDF
19. Controlled Growth of Porphyrin Wires at a Solid‐Liquid Interface
- Author
-
Jean Weiss, Yoshihiro Kikkawa, Christophe Kahlfuss, Jennifer A. Wytko, Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and National Institute of Advanced Industrial Science and Technology (AIST)
- Subjects
010405 organic chemistry ,Atomic force microscopy ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Interface (computing) ,Organic Chemistry ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Porphyrin ,Catalysis ,0104 chemical sciences ,Inorganic Chemistry ,Molecular wire ,chemistry.chemical_compound ,chemistry ,Chemical engineering ,Drug Discovery ,[CHIM.COOR]Chemical Sciences/Coordination chemistry ,Self-assembly ,Physical and Theoretical Chemistry ,Solid liquid - Abstract
International audience; Bis(zinc porphyrin) scaffolds bearing C8 or C18 alkyl chains and imidazole end groups self‐assembled in a head‐to‐tail fashion into multi‐porphyrin assemblies on both HOPG and mica. Due to weaker molecule surface‐interactions, longer arrays formed on mica than on HOPG. In both cases, it was essential first to generate monomers that were drop casted on the surface, then to allow time for the bis(zinc porphyrins) to assemble. Although thicker fibrous assemblies were observed with the C8 alkyl substituents than with the longer chains, noncovalent assemblies up to 1 μm long were observed for each molecule. These investigations provide a reproducible, noncovalent method to grow porphyrin arrays that may be of interest in molecular electronics for charge transport.
- Published
- 2019
20. Cover Feature: A New Phenanthroline Ligand and the Spontaneous Resolution of its Homoleptic Copper(I) Complex (Eur. J. Org. Chem. 47/2020)
- Author
-
Jean-Claude Chambron, Lydia Karmazin, Jordan L. Appleton, Jean Weiss, Vincent Silber, Romain Ruppert, and Corinne Bailly
- Subjects
chemistry.chemical_compound ,Crystallography ,chemistry ,Ligand ,Phenanthroline ,Organic Chemistry ,Resolution (electron density) ,chemistry.chemical_element ,Physical and Theoretical Chemistry ,Homoleptic ,Copper - Published
- 2020
21. Ultrasound assisted synthesis, characterization and electrochemical study of a tetradentate oxovanadium diazomethine complex
- Author
-
Moufida Merzougui, Kamel Ouari, and Jean Weiss
- Subjects
Schiff base ,010405 organic chemistry ,Organic Chemistry ,Analytical chemistry ,Glassy carbon ,010402 general chemistry ,Electrochemistry ,01 natural sciences ,Square pyramidal molecular geometry ,0104 chemical sciences ,Analytical Chemistry ,Inorganic Chemistry ,chemistry.chemical_compound ,chemistry ,X-ray crystallography ,Physical chemistry ,Cyclic voltammetry ,Rotating disk electrode ,Spectroscopy ,Monoclinic crystal system - Abstract
The oxovanadium (IV) complex “VOL” of a tetradentate Schiff base ligand derived from the condensation of diaminoethane and 2-hydroxy-1-naphthaldehyde was efficiently prepared via ultrasound irradiation and the template effect of VO(acac)2. The resulting product was characterized by elemental analysis, infrared, electronic absorption and molar conductance measurement. Single X-ray structure analysis showed that the complex is a monomeric five-coordinate with a distorted square pyramidal geometry. It crystallizes in monoclinic system having unit cell parameters a = 8.3960 (5) A; b = 12.5533 (8) A and c = 18.7804 (11) A; α = γ = 90°; β = 104.843°(2), with P 21/c space group. Cyclic voltammetry of the complex, carried out on a glassy carbon (GC) electrode in DMF, showed reversible cyclic voltammograms response in the potential range 0.15–0.60 V involving a single electron redox wave VV/VIV, the diffusion coefficient is determinedusing GC rotating disk electrode. The Levich plot Ilim = f(ω1/2), was used to calculate the diffusion-convection controlled currents.
- Published
- 2016
22. Stable isoporphyrin copolymer: Electrochemical mechanism and behavior and photovoltaic properties
- Author
-
Sylvie Choua, Helen Ibrahim, Jean Weiss, Nolwenn Le Breton, Moussa Boudiaf, Antoine Bonnefont, Vasilica Badets, Michel Goldmann, Laurent Ruhlmann, Raphaël Lamare, Yiming Liang, Embarek Bentouhami, Institut de Chimie de Strasbourg, Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), and Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
Photocurrent ,Materials science ,General Chemical Engineering ,02 engineering and technology ,Quartz crystal microbalance ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,01 natural sciences ,7. Clean energy ,Porphyrin ,0104 chemical sciences ,Dielectric spectroscopy ,Dication ,chemistry.chemical_compound ,chemistry ,Radical ion ,Hexafluorophosphate ,Electrochemistry ,Copolymer ,0210 nano-technology ,[CHIM.OTHE]Chemical Sciences/Other - Abstract
Two types of porphyrin copolymer thin films were obtained by electropolymerization of zinc-5,15-bis(p-tolyl)porphyrin. Electrogenerated porphyrin radical cation and dication are powerful electrophiles which can rapidly react with 1,1″-(1,3-propanediyl)bis-4,4′-bipyridinium hexafluorophosphate salt (bpy+–(CH2)3–+bpy·2PF6−) as nucleophiles to form copolymers containing stable isoporphyrin radicals or porphyrins, depending of the applied upper potential limit (1.0 V versus 1.6 V). Electrochemical routes leading to these electroactive copolymers are discussed and the unusual redox properties of copolymers containing stable isoporphyrin radicals are studied. The electropolymerization of the two copolymers was monitored by electrochemical quartz crystal microbalance (EQCM). The copolymers were characterized by UV–Vis–NIR spectroscopy, X-ray photoelectron spectroscopy (XPS), electrochemistry, electron spin resonance (ESR) and atomic force microscopy (AFM). Their electrical properties have been studied by electrochemical impedance spectroscopy and their photovoltaic performances have been investigated by photocurrent transient measurements under visible-NIR light irradiation. The isoporphyrin radical copolymer exhibited considerably better photocurrent generation when compared to the porphyrin copolymer.
- Published
- 2018
23. Ring-Oxidized Zinc(II) Phthalocyanine Cations: Structure, Spectroscopy, and Decomposition Behavior
- Author
-
Romain Ruppert, Sylvie Choua, Wen Zhou, Jean Weiss, Jennifer A. Wytko, Declan McKearney, Daniel B. Leznoff, Yumeela Ganga-Sah, Institut de Chimie de Strasbourg, Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), Laboratoire de Chimie Quantique, Centre National de la Recherche Scientifique (CNRS), and Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
010405 organic chemistry ,Dimer ,chemistry.chemical_element ,Protonation ,Zinc ,010402 general chemistry ,01 natural sciences ,3. Good health ,0104 chemical sciences ,Inorganic Chemistry ,Solvent ,chemistry.chemical_compound ,Crystallography ,Monomer ,chemistry ,Phthalocyanine ,Physical and Theoretical Chemistry ,Acetonitrile ,[CHIM.OTHE]Chemical Sciences/Other ,Tetrahydrofuran - Abstract
A bromonium oxidizing agent was used to produce a ring-oxidized zinc phthalocyanine (PcZn), [PcZn(solvent)]•2[BArF4]2 (1·solvent), in good yield. This material is dimeric in the solid state with one axially coordinated solvent [tetrahydrofuran (THF) or 1,2-dimethoxyethane (DME)] and close intradimer ring–ring distances of 3.18 and 3.136 A (THF and DME respectively); this proximity facilitates strong antiferromagnetic coupling to yield diamagnetic dimers. 1·THF is present in solution as a monomer and a dimer. In CH2Cl2, the dimer is favored above 0.1 mM, and it is almost exclusively present in solvents with a high dielectric constant such as acetonitrile. The material 1·THF/DME decomposes in DME to a meso-nitrogen-protonated species, [HPcZn(DME)2][BArF4] (2), which was isolated and represents the first example of such a structurally characterized, protonated, unsubstituted PcM complex. A partially oxidized dimer or “pimer” [(PcZn(DME))2]•[BArF4] (3) was also structurally characterized and has a intradimer ...
- Published
- 2018
24. Fluorescence Commutation and Surface Photopatterning with Porphyrin Tetradithienylethene Switches
- Author
-
Julien Boixel, Jean Weiss, Jennifer A. Wytko, Agostino Galanti, Paolo Samorì, Thomas Biellmann, Véronique Guerchais, Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut de Science et d'ingénierie supramoléculaires (ISIS), Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Agence Nationale de la Recherche through the Labex projects CSC within the Investissement d'Avenir program [ANR-10-LABX-0026 CSC, ANR-10-120 IDEX-0002-02], International Center for Frontier Research in Chemistry [JWe-CSC-0001], Universite de Strasbourg, Centre National de la Recherche Scientifique, Universite de Rennes, European Commission through the Marie Sklodowska-Curie project ITN project iSwitch [GA-642196], ANR-10-IDEX-0002,UNISTRA,Par-delà les frontières, l'Université de Strasbourg(2010), European Project: 642196,H2020,H2020-MSCA-ITN-2014,iSwitch(2015), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
- Subjects
010405 organic chemistry ,photopatterning ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Organic Chemistry ,Free base ,porphyrinoids ,General Chemistry ,Confocal scanning microscopy ,010402 general chemistry ,Photochemistry ,photochromism ,01 natural sciences ,Fluorescence ,Porphyrin ,Catalysis ,0104 chemical sciences ,[CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry ,chemistry.chemical_compound ,Photochromism ,chemistry ,dithienylethene ,Polystyrene ,fluorescence ,Absorption (chemistry) ,Luminescence - Abstract
International audience; Four tetradithienylethene (DTE) substituted porphyrins, the free base 1H(2), and three metal derivatives (1Zn, 1Co, 1Ni), were synthesized and studied. These dyads, for which the DTE units are connected to the porphyrin's meso positions via a meta-phenyl spacer, exhibit reversible photochromic properties in all cases, with conversion to the photostationary state (PSS) up to 88%, as confirmed by absorption and NMR spectroscopies. Compounds1H(2) and 1Zn are fluorescent in solution and display a red emission. Upon irradiation with UV light to trigger the closing of the DTEs, the fluorescence of both the free base and zinc porphyrin was very efficiently quenched in solution. The reversible, photo-switching of luminescence was retained in a tetra-DTE free-base porphyrin-doped polystyrene film, for which photo-patterning was demonstrated by confocal scanning microscopy. The tunable fluorescent properties of this multi-DTE framework render this compound of interest as a photo-rewritable fluorescent ink.
- Published
- 2018
25. A Highly Stable Organic Radical Cation
- Author
-
Monika Stolar, Thomas Baumgartner, Sylvie Choua, Christophe Gourlaouen, Corinne Boudon, Jennifer A. Wytko, Nolwenn Le Breton, Mathilde Berville, Jean Weiss, Laurent Ruhlmann, Jimmy Richard, Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and York University [Toronto]
- Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Organic Chemistry ,02 engineering and technology ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Reduction (complexity) ,chemistry.chemical_compound ,chemistry ,Radical ion ,Surface modification ,Physical and Theoretical Chemistry ,0210 nano-technology ,Derivative (chemistry) - Abstract
Functionalization of a methylviologen with four methyl ester substituents significantly facilitates the first two reduction steps. The easily generated radical cation shows markedly improved air stability compared to the parent methylviologen, making this derivative of interest in organic electronic applications.
- Published
- 2018
26. A water-soluble supramolecular complex that mimics the heme/copper hetero-binuclear site of cytochrome
- Author
-
Takehiro Ohta, Ryo Kamiya, Jennifer A. Wytko, Jean Weiss, Daiki Shimoji, Takashi Hayashi, Koji Kano, Yasuhiro Kudo, Hiroaki Kitagishi, Akira Onoda, Picobiology Institute, Graduate School of Life Science, University of Hyogo, Department of Applied Chemistry, Osaka University [Osaka], Department of Economics, University of Texas at Austin, University of Texas at Austin [Austin], Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC)
- Subjects
Dimer ,Supramolecular chemistry ,chemistry.chemical_element ,macromolecular substances ,010402 general chemistry ,01 natural sciences ,chemistry.chemical_compound ,Polymer chemistry ,polycyclic compounds ,Cytochrome c oxidase ,[CHIM.COOR]Chemical Sciences/Coordination chemistry ,Rotating disk electrode ,Heme ,Aqueous solution ,biology ,010405 organic chemistry ,Chemistry ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,technology, industry, and agriculture ,Active site ,General Chemistry ,Copper ,0104 chemical sciences ,carbohydrates (lipids) ,biology.protein ,lipids (amino acids, peptides, and proteins) - Abstract
The O2 adduct of an aqueous synthetic heme/copper model system built on a porphyrin/cyclodextrin supramolecular complex has been characterized., In mitochondria, cytochrome c oxidase (CcO) catalyses the reduction of oxygen (O2) to water by using a heme/copper hetero-binuclear active site. Here we report a highly efficient supramolecular approach for the construction of a water-soluble biomimetic model for the active site of CcO. A tridentate copper(ii) complex was fixed onto 5,10,15,20-tetrakis(4-sulfonatophenyl)porphinatoiron(iii) (FeIIITPPS) through supramolecular complexation between FeIIITPPS and a per-O-methylated β-cyclodextrin dimer linked by a (2,2′:6′,2′′-terpyridyl)copper(ii) complex (CuIITerpyCD2). The reduced FeIITPPS/CuITerpyCD2 complex reacted with O2 in an aqueous solution at pH 7 and 25 °C to form a superoxo-type FeIII–O2–/CuI complex in a manner similar to CcO. The pH-dependent autoxidation of the O2 complex suggests that water molecules gathered at the distal Cu site are possibly involved in the FeIII–O2–/CuI superoxo complex in an aqueous solution. Electrochemical analysis using a rotating disk electrode demonstrated the role of the FeTPPS/CuTerpyCD2 hetero-binuclear structure in the catalytic O2 reduction reaction.
- Published
- 2017
27. Flexible Viologen Cyclophanes: Odd/Even Effects on Intramolecular Interactions
- Author
-
Christophe Gourlaouen, Sylvie Choua, Saioa Cobo, Jennifer A. Wytko, Mathilde Berville, Corinne Boudon, Corinne Bailly, Jean Weiss, Laurent Ruhlmann, Eric Saint-Aman, Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide, Université de Strasbourg (UNISTRA), Département de Chimie Moléculaire - Chimie Inorganique Redox Biomimétique (DCM - CIRE ), Département de Chimie Moléculaire (DCM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019]), Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), and Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
010405 organic chemistry ,Diradical ,Viologen ,010402 general chemistry ,Photochemistry ,01 natural sciences ,Atomic and Molecular Physics, and Optics ,0104 chemical sciences ,law.invention ,Dication ,chemistry.chemical_compound ,chemistry ,law ,Intramolecular force ,medicine ,[CHIM]Chemical Sciences ,Physical and Theoretical Chemistry ,Methylene ,Electron paramagnetic resonance ,ComputingMilieux_MISCELLANEOUS ,Tetrathiafulvalene ,medicine.drug ,Cyclophane - Abstract
The ability of three bis-viologen cyclophanes to act as redox-triggered contractile switches is investigated. Odd/even effects in the formation of cyclic bis-viologens are circumvented by the use of a Zincke salt intermediate and a tetrathiafulvalene template to prepare a flexible cyclophane with hexyl linkers. Comparative spectro-electrochemical studies of this macrocycle with two other pentyl- or heptyl-linked cyclic bis-viologens show that the development of intramolecular interactions in aqueous solution depends on the length of the bridges. This dependence is confirmed by EPR and DFT studies of the magnetic coupling in the diradical dication species. The anti-ferromagnetic or ferromagnetic nature of the coupling depend, respectively, on the odd or even number of methylene groups in the spacer.
- Published
- 2017
28. Coordination controlled atropoisomerism in phenanthroline-strapped porphyrins: A swinging affair
- Author
-
Jennifer A. Wytko, Pauline Vorburger, and Jean Weiss
- Subjects
Hemeprotein ,biology ,Stereochemistry ,Phenanthroline ,chemistry.chemical_element ,General Chemistry ,Zinc ,Porphyrin ,Copper ,Zinc porphyrin ,chemistry.chemical_compound ,chemistry ,Polymer chemistry ,Pyridine ,biology.protein ,Cytochrome c oxidase - Abstract
A phenanthroline-strapped porphyrin bearing two pyridine side arms attached to opposite meso positions was designed as a potential cytochrome c oxidase model and its zinc and copper(I)-zinc complexes were prepared. In the zinc porphyrin complex, the pyridine arms underwent a rapid exchange of their coordination to the zinc atom on the open face of the strapped-porphyrin, as demonstrated by variable temperature NMR studies. Only the β2 atropoisomer was observed for the zinc complex because of the rapid exchange. This swinging motion no longer occurred when Cu I was bound within the phenanthroline strap. In this Cu I / Zn II complex, the αβ atropoisomer predominated and one pyridine was coordinated to the zinc atom on the proximal side and the other pyridine was bound to the copper on the distal face. This work shows that allostery can be effective to control atropoisomery in phenanthroline strapped porphyrin as heme protein models.
- Published
- 2014
29. Self-organized porphyrin arrays on surfaces: the case of hydrophilic side chains and polar surfaces
- Author
-
Mayuko Takahashi, Jennifer A. Wytko, Jean Weiss, Jonas Conradt, Masatoshi Kanesato, Vivien Rauch, Yoshihiro Kikkawa, and Heinz Kalt
- Subjects
Photocurrent ,chemistry.chemical_compound ,Dye-sensitized solar cell ,Chemistry ,Covalent bond ,Side chain ,Oxide ,General Chemistry ,Self-assembly ,Chromophore ,Photochemistry ,Porphyrin - Abstract
Energy collection in photosynthetic microorganisms occurs through vectorial energy transfer along organized assemblies of chromophores. This process has inspired many research groups and yielded numerous examples of self-assembled photoactive structures. Dye sensitization of solar cells usually requires covalent anchoring of dyes onto the surface of metal oxides. A new porphyrin derivative that self-assembles upon non-covalent interaction with a surface has been designed and characterized by AFM. Interaction with metal oxide surfaces is further documented by the sensitization of metal oxide surfaces and the generation of photocurrent in non-optimized dye sensitized solar cells.
- Published
- 2014
30. Inexpensive and Efficient Ullmann Methodology To Prepare Donor-Substituted Porphyrins
- Author
-
Romain Ruppert, José A. S. Cavaleiro, Jean-Paul Gisselbrecht, Khalissa Merahi, Julien Haumesser, Jean Weiss, Sylvie Choua, and Ana M. V. M. Pereira
- Subjects
Models, Molecular ,Molecular Structure ,Metalloporphyrins ,Chemistry ,Organic Chemistry ,Electron ,Crystallography, X-Ray ,Photochemistry ,Electrochemistry ,Biochemistry ,Porphyrin ,Electron spectroscopy ,Coupling (electronics) ,chemistry.chemical_compound ,Nickel ,Physical and Theoretical Chemistry - Abstract
The preparation of porphyrins functionalized with one or two carbazoles (or phenoxazines) is described. The electron donors were introduced into one or two porphyrin meso positions by using the inexpensive Ullmann coupling procedure. Very good yields were obtained, and for two new compounds, the X-ray structures were solved. Preliminary electrochemical data coupled with electronic spectroscopy are also reported.
- Published
- 2013
31. Highly Linear Self-Assembled Porphyrin Wires
- Author
-
Jean Weiss, Jonas Conradt, Lionel Allouche, Matthieu Koepf, Jennifer A. Wytko, Jȩdrzej Szmytkowski, Heinz Kalt, and Teodor Silviu Balaban
- Subjects
Inorganic Chemistry ,Zinc porphyrin ,chemistry.chemical_compound ,chemistry ,Linearity ,Imidazole ,Mica ,Physical and Theoretical Chemistry ,Photochemistry ,Luminescence ,Porphyrin ,Derivative (chemistry) ,Self assembled - Abstract
An efficient noncovalent assembly process involving high geometrical control was applied to a linear bis(imidazolyl zinc porphyrin) 7Zn, bearing C(18) substitutents, to generate linear multiporphyrin wires. The association process is based on imidazole recognition within the cavity of the phenanthroline-strapped zinc porphyrin. In chlorinated solvents, discrete soluble oligomers were obtained after (7Zn)(n) was end-capped with a terminal single imidazolyl zinc porphyrin derivative 4Zn. These soluble species, as well as their destabilization in the presence of protic solvents, were studied by UV-visible and time-resolved luminescence. In the solid state, assemblies as long as 480 nm, which corresponds to 190 iterative units or a total of 380 porphyrins, were observed by atomic force microscopy measurements on mica. The length and linearity of the porphyrin wires obtained illustrate the potential of phenanthroline-strapped porphyrins for the directional control of self-assembly processes.
- Published
- 2011
32. Synthesis and Characterization of a Novel Unsymmetrical Tetradentate Schiff Base Complex of Zinc(II) Derived from N,N′-bis (5-Bromosalicylidene) 2,3-Diaminopyridine (H2L): Crystal Structure of [Zn(II)L]Pyridine
- Author
-
Ali Ourari, Jean Weiss, and Kamel Ouari
- Subjects
Schiff base ,chemistry.chemical_element ,General Chemistry ,Crystal structure ,Zinc ,Triclinic crystal system ,Condensed Matter Physics ,Square pyramidal molecular geometry ,chemistry.chemical_compound ,Crystallography ,chemistry ,Pyridine ,Two-dimensional nuclear magnetic resonance spectroscopy ,Single crystal - Abstract
Yellow crystals of [Zn(N,N′-bis (5-bromosalicylidene) 2,3-diaminopyridine)] Pyridine, [Zn(C19H11Br2N3O2)]C5H5N, have been obtained and characterized by elemental analysis, FT-IR, UV–Vis, 1H NMR spectroscopy and MALDI-TOF mass spectrometry. The structure has been determined by single crystal X-ray crystallography. The complex crystallizes in the triclinic space group P-1 with two molecules in the asymmetric unit and with unit cell dimensions a = 8.0103(3) A, b = 12.8340(5) A, c = 22.3682(11) A, α = 91.715(2)°, β = 93.918(2)°, γ = 103.708(2)°. V = 2226.30(16) A3, Z = 4, R 1 = 0.0780 and wR 2 = 0.1192. X-ray structure determination revealed that the complex consists of a [Zn(C19H11Br2N3O2)] moiety with a coordinated pyridine molecule on the metallic centre. The zinc atom adopts a distorted square pyramidal geometry as it is shown in the crystal structure. A single crystal description of a unsymmetrical structure, spectroscopic and characterization with 2D NMR ROESY spectrum
- Published
- 2010
33. Molecular Tools for the Self-Assembly of Bisporphyrin Photodyads: A Comprehensive Physicochemical and Photophysical Study
- Author
-
Frederic Melin, Ali Trabolsi, Jennifer A. Wytko, Matthieu Koepf, Hassan Traboulsi, Mourad Elhabiri, Anne Marie Albrecht-Gary, Jean Weiss, and Jérémy Brandel
- Subjects
Porphyrins ,Molecular Structure ,Chemistry, Physical ,Metalloporphyrins ,Photochemistry ,Hydrogen bond ,Phenanthroline ,Imidazoles ,Substrate (chemistry) ,Hydrogen Bonding ,Ligands ,Porphyrin ,Inorganic Chemistry ,Kinetics ,Zinc ,chemistry.chemical_compound ,chemistry ,Spectrophotometry, Ultraviolet ,Physical and Theoretical Chemistry ,Phenanthrolines - Abstract
Accessible and hindered phenanthroline-strapped Zn(II) porphyrin receptors exhibited suitable topography tailored to strongly and selectively bind N(1)-unsubstituted imidazoles and imidazoles appended to free-base porphyrins. Distal binding was clearly driven by the formation of strong bifurcated hydrogen bonds with the phenanthroline unit of the receptors. An extensive physicochemical study emphasized the influence of bulkiness of the substrate and of the porphyrin receptor on the binding and self-assembly mechanism. Knowledge of the corresponding spectroscopic, thermodynamic, and kinetic data were of fundamental importance to elucidate and to model the photoinduced properties which occur within the self-assembled porphyrin dyads.
- Published
- 2009
34. Surface-Tuned Assembly of Porphyrin Coordination Oligomers
- Author
-
Jennifer A. Wytko, Jean-Pierre Bucher, Jean Weiss, and Matthieu Koepf
- Subjects
chemistry.chemical_classification ,Inorganic chemistry ,chemistry.chemical_element ,General Chemistry ,Polymer ,Zinc ,Biochemistry ,Porphyrin ,Catalysis ,chemistry.chemical_compound ,Crystallography ,Colloid and Surface Chemistry ,Monomer ,chemistry ,Imidazole ,Mica ,Graphite ,Alkyl - Abstract
Two self-complementary phenanthroline-strapped porphyrins bearing imidazole arms and C 12 or C 18 alkyl chains were synthesized, and their surface self-assembly was investigated by atomic force microscopy (AFM) on mica and highly ordered pyrrolitic graphite (HOPG). Upon zinc(II) complexation, stable porphyrin dimers formed, as confirmed by DOSY (1)H NMR and UV-visible spectroscopy. In solution, the dimers formed J-aggregates. AFM studies of the solutions dip-coated onto mica or drop-casted onto HOPG revealed that the morphologies of the assemblies formed were surface-tuned. On mica, fiber-like assemblies of short stacks of J-aggregates were observed. The strong influence of the mica's epitaxy on the orientation of the fibers suggested a surface-assisted assembly process. On HOPG, interactions between the alkyl chains and the graphite surface resulted in the stabilization and trapping of monomer species followed by their subsequent association into coordination polymers on the surface. Interdigitation of the alkyl chains of separate polymer strands induced lateral association of wires to form islands that grew preferentially upon drop-casting and slow evaporation. Clusters of laterally assembled wires were observed for the more mobile functionalized porphyrins bearing C 12 chains.
- Published
- 2008
35. Electrocatalytic reduction of oxygen with phenanthroline-strapped porphyrins
- Author
-
Philippe Ochsenbein, Jean Weiss, Maurice Gross, Michel Bonin, Kurt Schenk, Corinne Boudon, Mamadou Lo, and Frederic Melin
- Subjects
chemistry.chemical_classification ,Ligand ,Phenanthroline ,Inorganic chemistry ,chemistry.chemical_element ,General Chemistry ,Zinc ,Electrochemistry ,Porphyrin ,Copper ,chemistry.chemical_compound ,chemistry ,Platinum ,Alkyl - Abstract
The electrochemical behavior of three cytochrome c oxidase models has been investigated. All the models are derived from a phenanthroline-strapped, porphyrin framework that binds zinc(II) or iron(III) chloride in the porphyrin subunit, and copper(I) in the phenanthroline site. The iron complex and the bimetallic zinc(II) copper(I) complex of the parent ligand have been characterized by X-ray diffraction. One model consists of the parent structure on which C 12 alkyl chains have been added. This soluble model achieves electrochemical 2-electron reduction of oxygen in organic solvents without the addition of an exogenous axial base, and in the presence of an organic or inorganic source of protons. The two other models comprise the parent phenanthroline-strapped porphyrin framework, on which two pendant imidazoles have been incorporated. These models adsorbed on ring-disk electrodes with an edge-oriented, pyrolytic graphite (EOPG) disk and a platinum ring, efficiently catalyze the 4-electron reduction of oxygen in dioxygen saturated water at neutral pH.
- Published
- 2007
36. Viologen cyclophanes: redox controlled host-guest interactions
- Author
-
Jennifer A. Wytko, Mathilde Berville, Lydia Karmazin, and Jean Weiss
- Subjects
Valence (chemistry) ,Diradical ,Chemistry ,Metals and Alloys ,Viologen ,General Chemistry ,Photochemistry ,Redox ,Catalysis ,Surfaces, Coatings and Films ,Electronic, Optical and Magnetic Materials ,chemistry.chemical_compound ,Materials Chemistry ,Ceramics and Composites ,medicine ,Methyl Viologen ,Tetrathiafulvalene ,medicine.drug - Abstract
Viologens can exist in three redox states varying from dicationic to neutral. This work emphasizes the control of the host–guest properties in bis-viologen cyclophanes. Two flexible cyclophanes were prepared by a cyclisation method sensitive to the odd/even number of carbons in the flexible chains linking two viologens. C5 and C7 cyclophanes were characterised by X-ray diffraction in their tetracationic state and their diradical dicationic state. In the presence of tetrathiafulvalene or methyl viologen as guests, inclusion complexes were obtained, including a mixed valence species.
- Published
- 2015
37. Trapping Nanostructures on Surfaces through Weak Interactions
- Author
-
Yoshihiro Kikkawa, Masatoshi Kanesato, Ismail Hijazi, Antoine Goujon, Stéphane Campidelli, Jennifer A. Wytko, Matthieu Koepf, Jean Weiss, Vivien Rauch, Institut de Chimie de Strasbourg, Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), National Institute of Advanced Industrial Science and Technology (AIST), Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN UMR 3685), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), and Laboratoire Innovation en Chimie des Surfaces et NanoSciences (LICSEN)
- Subjects
chemistry.chemical_classification ,Organic Chemistry ,General Chemistry ,Polyethylene glycol ,[CHIM.MATE]Chemical Sciences/Material chemistry ,Evaporation (deposition) ,Catalysis ,chemistry.chemical_compound ,Molecular wire ,chemistry ,Highly oriented pyrolytic graphite ,Chemical engineering ,Organic chemistry ,Self-assembly ,Mica ,Methylcyclohexane ,Alkyl - Abstract
International audience; The assembly of imidazole-functionalized phenan-throline-strapped zinc porphyrins (ZnPorphen)w ith alkyl or polyethylene glycol (PEG) side chains was studied in solution and by AFM after casting on highly oriented pyrolytic graphite (HOPG) or mica. The natureo ft he solvent and its evaporation time influenced the morphology of the objectso b-served.O nH OPG, short rods of about 100 nm were observed after fast evaporation of solutions of the alkyl derivatives in CHCl 3 ,T HF,o rp yridine, whereas islands of aligned rows of longer wires were obtained from methylcyclohexane (MCH). Slow evaporation of MCH led to at hree-dimensional assembly. The PEG porphyrin assembled into short wires on HOPG or fibers on mica after slow evaporation of solutions in THF.T his study shows the role of surface–molecule interactions in the interfacial assembly of ZnPorphen derivatives and contributes to understanding the parameters that control their noncovalent assembly into molecular wires on as urface.
- Published
- 2015
38. Built-in Axial Base Binding on Phenanthroline-Strapped Zinc(II) and Iron(III) Porphyrins
- Author
-
Sylvie Choua, Jean Weiss, Philippe Turek, Frederic Melin, and Maxime Bernard
- Subjects
Porphyrins ,Molecular Structure ,Iron ,Phenanthroline ,Inorganic chemistry ,Cytochromes c ,chemistry.chemical_element ,Zinc ,Copper ,law.invention ,Inorganic Chemistry ,chemistry.chemical_compound ,Models, Chemical ,chemistry ,Catalytic cycle ,law ,Polymer chemistry ,Proton NMR ,Imidazole ,Physical and Theoretical Chemistry ,Electron paramagnetic resonance ,Selectivity ,Phenanthrolines - Abstract
In addition to the need for functional models of cytochrome c oxidase, structural models are still required for a better understanding of the small reorganizations occurring during the catalytic cycle. An efficient synthetic approach has been designed to prepare several phenanthroline-strapped porphyrins, two of them bearing two pendant imidazoles. These built-in bases are both potentially able to act as axial bases for the metalloporphyrin and as complementary ligands for copper if necessary. Diamagnetic zinc(II) was used to demonstrate that the distal/proximal selectivity demonstrated by exogenic bases binding studies can be extended to the coordination of iron(III). Combination of EPR and paramagnetic 1H NMR shows that the imidazole binding on the zinc species can be further extended to the iron(III) species in dilute conditions.
- Published
- 2006
39. Synthesis of a highly soluble superstructured phenanthroline strapped porphyrin
- Author
-
Jean Weiss, Matthieu Koepf, Jérôme Jaillard, and Frederic Melin
- Subjects
chemistry.chemical_compound ,chemistry ,Scale (ratio) ,Phenanthroline ,Organic Chemistry ,Drug Discovery ,Surface modification ,Organic chemistry ,Solubility ,Biochemistry ,Porphyrin - Abstract
A highly soluble phenanthroline strapped porphyrin is prepared on multigram scale by appropriate functionalization with C 12 chains after the cyclization of the tetrapyrrolic macrocycle.
- Published
- 2005
40. Induced Fit Process in the Selective Distal Binding of Imidazoles in Zinc(II) Porphyrin Receptors
- Author
-
Dharam Paul, Jean Weiss, Frederic Melin, Michel Bonin, Jennifer A. Wytko, Patrick Maltese, Kurt Schenk, Caroline Hirtz, and Philippe Ochsenbein
- Subjects
Inorganic Chemistry ,chemistry.chemical_compound ,chemistry ,Stereochemistry ,chemistry.chemical_element ,Imidazole ,Zinc ,Physical and Theoretical Chemistry ,Receptor ,Porphyrin ,Affinities - Abstract
The respective affinities of various imidazole derivatives, imidazole (ImH), 2-methylimidazole (2-MeImH), 2-phenylimidazole (2-PhImH), N-methylimidazole (N-MeIm), 2-methylbenzimidazole (2-MeBzImH), and 4,5-dimethylbenzimidazole (4,5-Me(2)BzImH), for two phenanthroline (Phen) strapped zinc(II) porphyrin receptors porphen-Zn 1-Zn and 2-Zn have been studied. The formation of a supplementary H-bond considerably enhances the affinity of the zinc(II)-porphen receptor for imidazoles unsubstituted on the pyrrolic nitrogen (ImH) versus N-substituted imidazoles such as N-MeIm. The ImHs subset porphen-Zn complexes are formed with association constants up to 4 orders of magnitude superior to those measured either for N-MeIm as substrate or TPP-Zn as receptor. Distal or proximal binding of the substrates was determined by (1)H NMR measurements and titration. In two cases, the very high stability of the inclusion complex enabled the use of 2D NMR techniques. Excellent correlation between solution and solid-state structures has been obtained. A total of six X-ray structures are detailed in this article showing that the evolution of the shape of the zinc(II) receptor is mostly dependent on the steric constraints induced by the substitution on the imidazole. Hindered guests also progressively induce considerable mobility restrictions and severe distortions on the receptor, especially in the case of 2-MeBzImH and 2-PhImH.
- Published
- 2003
41. Front Cover: CuAAC in a Distal Pocket: Metal Active-Template Synthesis of Strapped-Porphyrin [2]Rotaxanes (Chem. Eur. J. 55/2017)
- Author
-
Yuta Miyazaki, Ayumu Ogawa, Takashi Hayashi, Jean Weiss, Jennifer A. Wytko, Christophe Kahlfuss, Koji Oohora, and Takashi Matsumoto
- Subjects
Metal ,chemistry.chemical_compound ,Front cover ,Chemistry ,visual_art ,Organic Chemistry ,Polymer chemistry ,visual_art.visual_art_medium ,General Chemistry ,Template synthesis ,Porphyrin ,Catalysis ,Cycloaddition - Published
- 2017
42. Spectroscopic, crystal structural and electrochemical studies of zinc(II)-Schiff base complex obtained from 2,3-diaminobenzene and 2-hydroxy naphthaldehyde
- Author
-
Jean Weiss, Sabrina Bendia, Corinne Bailly, and Kamel Ouari
- Subjects
Magnetic Resonance Spectroscopy ,Spectrophotometry, Infrared ,Proton Magnetic Resonance Spectroscopy ,Molecular Conformation ,chemistry.chemical_element ,Zinc ,Naphthalenes ,Phenylenediamines ,Crystallography, X-Ray ,Ligands ,Analytical Chemistry ,Crystal ,chemistry.chemical_compound ,Coordination Complexes ,Electrochemistry ,Carbon-13 Magnetic Resonance Spectroscopy ,Instrumentation ,Spectroscopy ,Schiff Bases ,Coordination geometry ,Schiff base ,Ligand ,Electric Conductivity ,Benzene ,Electrochemical Techniques ,Atomic and Molecular Physics, and Optics ,Crystallography ,chemistry ,Orthorhombic crystal system ,Spectrophotometry, Ultraviolet ,Cyclic voltammetry ,Single crystal - Abstract
Mononuclear zinc(II) complex, [Zn(II)L], where L is a dianionic ligand, has been synthesized and characterized by elemental analysis, electronic, IR and NMR [1H, 13C, DEPT, 1H–1H COSY, ROESY, HSQC and HMBC] spectroscopic techniques. Structural analysis of the complex by single crystal X-ray crystallography shows the presence of a distorted square planar coordination geometry (NNOO) of the metal center. The crystal of the title complex C28H18N2O2Zn belongs to the orthorhombic system with space group Pmn21. Electrochemical behavior of the Zn(II)L complex has been investigated by cyclic voltammetry on glassy carbon and platinum electrodes in DMF at 100 mV/s scan rate.
- Published
- 2014
43. ChemInform Abstract: Inexpensive and Efficient Ullmann Methodology to Prepare Donor-Substituted Porphyrins
- Author
-
Julien Haumesser, Romain Ruppert, Jean-Paul Gisselbrecht, Khalissa Merahi, Ana M. V. M. Pereira, José A. S. Cavaleiro, Jean Weiss, and Sylvie Choua
- Subjects
Coupling (electronics) ,chemistry.chemical_compound ,chemistry ,General Medicine ,Electron ,Electrochemistry ,Electron spectroscopy ,Porphyrin ,Combinatorial chemistry - Abstract
The preparation of porphyrins functionalized with one or two carbazoles (or phenoxazines) is described. The electron donors were introduced into one or two porphyrin meso positions by using the inexpensive Ullmann coupling procedure. Very good yields were obtained, and for two new compounds, the X-ray structures were solved. Preliminary electrochemical data coupled with electronic spectroscopy are also reported.
- Published
- 2014
44. [Untitled]
- Author
-
Jean Weiss
- Subjects
chemistry.chemical_classification ,chemistry.chemical_compound ,Molecular recognition ,Chemistry ,Hydrogen bond ,chemistry.chemical_element ,Zinc ,Receptor ,Combinatorial chemistry ,Porphyrin ,Multi point ,Coordination complex - Abstract
The tremendous efforts made in order to control the coordination chemistry of hemoprotein models have considerably enhanced the synthesis of functionalized porphyrins, whose carefully designed architectures allowed for selective bindings of exogenic substrates. The common use of zinc(II) in place of pentacoordinated iron(II) has induced the use of zinc(II) porphyrins as building blocks for selective receptors. These receptors offer a convenient combination of multi-point recognition of substrates, and monitoring of the complexation due to the chromophoric nature of the tetrapyrrolic unit. This review is dedicated to recent progress made in the field of molecular recognition involving multi-point selective binding processes, in whichthe establishment of a strong coordination bond is finely tuned by one or more weak interactions adequately introduced in the architecture of a functionalized zinc(II)-porphyrin.
- Published
- 2001
45. Recognition of Imidazoles by Strapped Zinc(II) Porphyrin Receptors: Insight into the Induced-Fit Mechanism
- Author
-
Jérémy Brandel, Mourad Elhabiri, Ali Trabolsi, Anne Marie Albrecht-Gary, Jean Weiss, and Frederic Melin
- Subjects
Inorganic Chemistry ,chemistry.chemical_compound ,Metalloporphyrins ,Chemistry ,Stereochemistry ,Imidazoles ,chemistry.chemical_element ,Imidazole ,Receptors, Cell Surface ,Zinc ,Physical and Theoretical Chemistry ,Receptor ,Porphyrin - Abstract
Imidazole-porphyrin coordination has become an important tool in the design of self-assembled materials. A combination of spectrophotometric and stopped-flow techniques has been used to gain insight into the control of imidazole binding in the distal pocket of phenanthroline-strapped porphyrins. The binding studies of a variety of imidazole substrates in combination with both hindered and accessible receptors have permitted the determination of the thermodynamic and kinetic parameters associated with the imidazole binding.
- Published
- 2007
46. Efficient combination of calix[4]arenes and meso-diphenylporphyrins
- Author
-
Jean Weiss and Robert Milbradt
- Subjects
Quenching (fluorescence) ,Ligand ,Organic Chemistry ,Photochemistry ,Biochemistry ,Porphyrin ,Benzoquinone ,Benzaldehyde ,chemistry.chemical_compound ,chemistry ,Yield (chemistry) ,Drug Discovery ,Calixarene ,Polymer chemistry - Abstract
The selective mono-alkylation of a calix[4]arene with a functionalized benzaldehyde followed by the condensation with dipyrrylmethane afforded in good yield a porphyrin substituted by two calix[4]arenes. The same multisite ligand was alternatively obtained by double monoalkylation of two calix[4]arenes with a functionalized porphyrin. The two calixarene units are in cone shape and thus can accomodate neutral organic guests. The efficiency of the fluorescence quenching of two porphyrins by benzoquinone has been evaluated and compared. In a first approximation, Stern-Volmer plots provide evidence for an enhanced quenching when calixarene hosts are bound to the porphyrin.
- Published
- 1995
47. Dynamic assembly of porphyrin wires trapped on a highly oriented pyrolitic graphite surface
- Author
-
Mayuko Takahashi, Vivien Rauch, Yoshihiro Kikkawa, Jennifer A. Wytko, Masatoshi Kanesato, and Jean Weiss
- Subjects
Surface (mathematics) ,Morphology (linguistics) ,Chemistry ,Organic Chemistry ,Photochemistry ,Biochemistry ,Porphyrin ,Solvent ,chemistry.chemical_compound ,Monomer ,Chemical engineering ,Imidazole ,Graphite ,Physical and Theoretical Chemistry ,Deposition (law) - Abstract
Carefully designed porphyrin building blocks assemble through selective imidazole binding in various solvents to form linear multiporphyrin objects. From a dynamic mixture of monomers, dimers, and oligomers, linear objects were observed on a highly oriented pyrolitic graphite (HOPG) surface. On the surface, the objects’ morphology clearly depended on the solvent used for deposition and was modified upon heating.
- Published
- 2012
48. Comparative studies in series of cytochrome c oxidase models
- Author
-
Bernard Boitrel, Jean Weiss, Christian Ruzié, Corinne Boudon, Petra Hellwig, Mamadou Lo, Ismail Hijazi, Frederic Melin, Nesrine Oueslati, Aurélien Trivella, Jennifer A. Wytko, Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de glaciologie et géophysique de l'environnement (LGGE), Observatoire des Sciences de l'Univers de Grenoble (OSUG), Université Joseph Fourier - Grenoble 1 (UJF)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Institut national des sciences de l'Univers (INSU - CNRS)-Institut national de recherche en sciences et technologies pour l'environnement et l'agriculture (IRSTEA)-Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry])-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Institut national des sciences de l'Univers (INSU - CNRS)-Institut national de recherche en sciences et technologies pour l'environnement et l'agriculture (IRSTEA)-Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry])-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes-Centre National de la Recherche Scientifique (CNRS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry])-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP)-Institut national de recherche en sciences et technologies pour l'environnement et l'agriculture (IRSTEA)-Université Joseph Fourier - Grenoble 1 (UJF)-Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes (UGA)-Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry])-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP)-Institut national de recherche en sciences et technologies pour l'environnement et l'agriculture (IRSTEA)-Université Joseph Fourier - Grenoble 1 (UJF)-Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes (UGA)-Centre National de la Recherche Scientifique (CNRS), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences de l'Univers (INSU - CNRS)-Observatoire des Sciences de l'Univers de Grenoble (OSUG), Université Joseph Fourier - Grenoble 1 (UJF)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Institut national des sciences de l'Univers (INSU - CNRS)-Institut national de recherche en sciences et technologies pour l'environnement et l'agriculture (IRSTEA)-Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry])-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Institut national de recherche en sciences et technologies pour l'environnement et l'agriculture (IRSTEA)-Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry])-Centre National de la Recherche Scientifique (CNRS), Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Rennes-Université de Rennes 1 (UR1), and Université de Rennes (UNIV-RENNES)
- Subjects
Stereochemistry ,chemistry.chemical_element ,Heme ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Ferrous ,Catalysis ,Inorganic Chemistry ,Metal ,Electron Transport Complex IV ,chemistry.chemical_compound ,Electrochemistry ,Cytochrome c oxidase ,Binding site ,chemistry.chemical_classification ,Binding Sites ,biology ,010405 organic chemistry ,Chemistry ,[CHIM.CATA]Chemical Sciences/Catalysis ,Copper ,0104 chemical sciences ,Heme A ,Enzyme ,Metals ,visual_art ,visual_art.visual_art_medium ,biology.protein - Abstract
International audience; This study compares the behavior as cytochrome c oxidase (CcO) functional and structural models of a series of reported and unreported ligands that provide either a binding site for copper without a built-in proximal base, or both a flexible binding site for copper and a built-in proximal base, or a fixed binding site for copper with a built-in proximal base. The comparisons of the models show that the relative position of the two metal sites is not only a crucial parameter in the control of the catalytic behavior but also essential in mimicking other features of the enzyme such as CO exchange between the ferrous heme a(3) and the cuprous Cu(B) center.
- Published
- 2011
49. Synthesis and properties of double-calix[4]-arenes, doubly-crowned calix[4]-arenes, and double-calix-crowns
- Author
-
Jacques Vicens, Zouhair Asfari, Jean Weiss, and S. Pappalardo
- Subjects
Chemistry ,Stereochemistry ,General Chemical Engineering ,General Chemistry ,Nuclear magnetic resonance spectroscopy ,Polyethylene glycol ,Alkali metal ,Potassium carbonate ,chemistry.chemical_compound ,Calixarene ,Polymer chemistry ,Molecule ,Acetonitrile ,Cyclophane - Abstract
Syntheses of double-calix(4)arenes, doubly- crowned calix(4larenes, and double-calix-crowns have been achieved by reacting p-tert-butylcalix(4larene or a new mesitol based calixL41arene with various polyethylene glycol ditosylates in the presence of potassium carbonate in refluxing acetonitrile. Depending on the nature of the ditosylate and on the reaction times are differently obtained calixarene ligands. The complexation properties toward alkali cations are presented for the double-calix-crown derived of p-tert-butylcalix(4larene.
- Published
- 1993
50. Double-Calixarene Design, Synthesis, and Properties
- Author
-
Jacques Vicens, Zouhair Asfari, and Jean Weiss
- Subjects
chemistry.chemical_classification ,chemistry.chemical_compound ,Polycyclic compound ,Design synthesis ,Chemistry ,Organic Chemistry ,Calixarene ,Organic chemistry ,Cyclophane - Published
- 1993
Catalog
Discovery Service for Jio Institute Digital Library
For full access to our library's resources, please sign in.