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52. Crown-annelated tetrathiafulvalenes: synthesis of new functionalised derivatives and spectroscopic and electrochemical studies of metal complexation

Author

Dieing, Reinhold, primary, Morisson, Vincent, additional, Moore, Adrian J., additional, Goldenberg, Leonid M., additional, Bryce, Martin R., additional, Raoul, Jean-Michel, additional, Petty, Michael C., additional, Garín, Javier, additional, Savirón, María, additional, Lednev, Igor K., additional, Hester, Ronald E., additional, and Moore, John N., additional

Published
1996
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56. New functionalized tetrathiafulvalenes: X-ray crystal structures and physico-chemical properties of TTF–C(O)NMe2and TTF–C(O)–O–C4H9: a joint experimental and theoretical study

Author

Batsanov, Andrei S., primary, Bryce, Martin R., additional, Heaton, Julie N., additional, Moore, Adrian J., additional, Skabara, Peter J., additional, Howard, Judith A. K., additional, Ortí, Enrique, additional, Viruela, Pedro M., additional, and Viruela, Rafael, additional

Published
1995
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60. Synthesis of Monofunctionalized Tetrathiafulvalene (TTF) Derivatives by Reactions of Tetrathiafulvalenyllithium with Electrophiles: X-ray Crystal Structures of Four TTF Derivatives Bearing Amide, Thioamide, and Thioester Substituents

Author

Batsanov, Andrei S., primary, Bryce, Martin R., additional, Cooke, Graeme, additional, Dhindsa, Ajaib S., additional, Heaton, Julie N., additional, Howard, Judith A. K., additional, Moore, Adrian J., additional, and Petty, Michael C., additional

Published
1994
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80. Synthesis and crystal engineering of new halogenated tetrathiafulvalene (TTF) derivatives and their charge transfer complexes and radical ion salts<fnoteref idrefs="fn1"></fnoteref><footnote id="fn1">Electronic supplementary information (ESI) available: a table of intermolecular contacts for compounds <compoundref idrefs="chem2">2</compoundref>, <compoundref idrefs="chem5">5</compoundref>, <compoundref idrefs="chem6">6</compoundref>, <compoundref idrefs="chem8">8</compoundref>, <compoundref idrefs="chem15">15</compoundref>, <compoundref idrefs="chem3">3</compoundref>·TCNQ, <compoundref idrefs="chem4">4</compoundref>·TCNQ, <compoundref idrefs="chem1">1</compoundref>·<compoundref idrefs="chem18">18</compoundref>, <compoundref idrefs="chem1">1</compoundref>·<compoundref idrefs="chem19">19</compoundref>·2C<SUB>4</SUB>H<SUB>8</SUB>O<SUB>2</SUB>, <compoundref idrefs="chem5">5</compoundref>+&z.rad;I<SUB>3</SUB>−·I<SUB>2</SUB> and <comp

Author

Batsanov, Andrei S., Bryce, Martin R., Chesney, Antony, Howard, Judith A. K., John, Derek E., Moore, Adrian J., Wood, Clare L., Gershtenman, Hagit, Becker, James Y., Khodorkovsky, Vladimir Y., Ellern, Arkady, Bernstein, Joel, Perepichka, Igor F., Rotello, Vincent, Gray, Mark, and Cuello, Alejandro O.

Abstract

Efficient syntheses are reported for tetraiodotetrathiafulvalene 2, 4-iodo-5-methyl-4',5'-bis(methylsulfanyl)TTF 3, and 4-iodo-4',5'-bis(methylsulfanyl)TTF 4 by iodination, using perfluorohexyl iodide, of lithiated derivatives of the corresponding TTF system. Bromination and chlorination of lithiotrimethylTTF using 1,2-dibromotetrafluoroethane and hexachloroethane gave 4-bromo- and 4-chloro-4',5,5'-trimethylTTF 6 and 7, respectively. Phosphite-induced self-coupling or cross-coupling reactions of 4-iodo-1,3-dithiole-2-thione or 4,5-diiodo-1,3-dithiole-2-thione(one) half-units resulted in TTF derivatives with partial loss of the iodine substituent(s). 4,5-Dibromo-4',5'-bis(cyanoethylsulfanyl)TTF 15 was prepared by cross-coupling methodology, and converted into 4,5-dibromo-4',5'-bis(methylsulfanyl)TTF 16 by reaction with caesium hydroxide and then methyl iodide. EPR data are reported for the electrochemically generated cation radicals of trimethylTTFX derivatives (X = I, Br and Cl) 5–7, respectively. For the neutral donors, the X-ray crystal structures are reported for 2, 5, 6, tetramethylTTF 8 and 15. Structure 2 is characterised by a particularly dense packing with continuous chains of intra-stack I⋯I contacts (4.17–4.19 Å). The crystals of 6 and 8 are isomorphous, while the structure of 5 is different. The iodo-substituent in 5 affects the packing in a way the bromo-substituent in 6 does not, due to differences in specific interactions rather than steric demands of I and Br, which are similar. Structure 15 comprises face-to-face dimers with inter-dimer Br⋯Br (3.57 Å) and Br⋯S (3.55 Å) contacts: a remarkable difference in bond distances between the Br and S-substituted dithiole rings is observed. The 1 ∶ 1 charge-transfer (CT) complexes 3·TCNQ and 4·TCNQ (TCNQ = 7,7,8,8-tetracyano-p-quinodimethane, 17) display mixed stair-like stacks of alternating D and A moieties: the overall degree of CT is estimated from bond length analysis to be 0.2 e and 0.3 e, respectively. In 3·TCNQ either position of the disordered iodine atom has one short (inter-stack, but intra-layer) contact with a cyano group (I⋯N distances of 3.14 and 3.18 Å). In 4·TCNQ a similar I⋯N contact is much longer (3.35 Å). In the structure of 5+·I3−·½I2 the cation radical is disordered; dimeric cation radicals display short intra-dimer contacts (S⋯S 3.38–3.39 Å, C⋯C 3.35 Å) consistent with electron coupling. Each dimer is surrounded by four I3− anions. The crystal structure of 16+·I3− is comprised of layers with interplanar separations of 3.55 Å. Cations of one layer overlap with anions of the next, and the packing can be described as mixed stacks parallel to the a axis. The remarkably high conductivity of this salt for a system of 1 ∶ 1 stoichiometry (σrt = 8 × 10−2 S cm−1) is ascribed to partial charge transfer (the charge on the TTF moiety is estimated as +⅔ from bond length analysis) and a continuous system of short non-bonding contacts.

Published
2001

81. π-Extended nitrofluorene-1,3-dithiole chromophore: enhancing the photoresponse of holographic materials through the balance of intramolecular charge transfer and electron affinity

Author

*, Dmitrii F. Perepichka, †, Perepichka, Igor F., Bryce, Martin R., Sokolov, Nikolai I., and Moore, Adrian J.

Abstract

The synthesis, electrochemistry, and electron absorption spectra of the novel push–pull type acceptor, 9-{[4,5-bis(hexylthio)-1,3-dithiol-2-ylidene]ethylidene}-2,4,5,7-tetranitrofluorene 3 is reported. A bathochromic shift and increased intensities of intramolecular charge transfer bands (compared to 1) are well-balanced with the electron affinity of the acceptor, which results in a pronounced increase of the photoresponse of carbazole-containing photothermoplastic optical information storage materials in the long wavelength visible and near infrared regions.

Published
2001

86. Dramatized-performative narrative : a novel method for composing electroacoustic music

Author

Savva, Dimitrios and Moore, Adrian J.

Abstract

This research introduces the term dramatized-performative narrative within the field of electroacoustic composition. It takes the form of an original portfolio of electroacoustic compositions, accompanied by a written text that explains: (1) the notion of dramatized-performative narrative, (2) a central method, based on this notion, that is employed throughout an accompanying portfolio of works, and (3) a brief discussion and analysis for each work in the portfolio. The term dramatized-performative narrative is proposed to specify a bespoke type of narrative that derives from, and directs, the performative activities of others. Based on this idea, a compositional method for producing works that incorporate dramatized-performative narrative is proposed. The method specifically explores, and experiments with, various ways of: (1) predetermining dramatized performances through the use of a performance-score, (2) sonically capturing the executions of these performances with various recording techniques, and (3) using these recordings as the central material for composing and structuring electroacoustic works of music. The works that have been composed using this method are: four 8-channel compositions: Moments of Liberty, I - IV, and the three stereo compositions: Echo, the nymph of reflection and Once there was a forest, I and II. Taken as a whole, the compositions highlight the compositional, musical and narrative potential of this novel method. The accompanying text begins with a brief introduction to the central writings on narrative and referential sound in electroacoustic music. It goes on to define the term dramatized-performative narrative in electroacoustic music, while setting out a series of research aims and objectives. Finally, it discusses the method itself and its relation to dramatized-performative narrative, and provides a brief analysis of each work in the accompanying portfolio.

Published
2021

90. Blue Dragon, White Tiger : the paradox of flux and flow in sound art and martial arts

Author

McEvoy, Caterina and Moore, Adrian J.

Subjects
781.3
Abstract

This portfolio consists of seven works: five electroacoustic compositions and two longer durational sound art installation works, which are products of practice-based research. The written commentary explores concepts and ideas found in Chinese aesthetics and Eastern philosophy and links to a discussion of the creative process behind the pieces. As a seasoned martial artist, I find I connect my own practice and experience to my compositional processes. The malleability of movement and change is a key aspect of my earlier works, and transformation becomes key in the later sound art installation pieces in this portfolio. The titles of some of the works are influenced by chapters in the Dao de jing (168 BC) or Book of Changes, which created a context for exploration of Daoist principles as part of my creative process. The principles of transition and flux are of interest to me both as a sound artist and martial artist. The interaction between energy and oscillatory phenomena are prevalent to both martial arts (Yin and Yang) and electroacoustic music (where one might situate and navigate sound through a series of polar opposites). As an artist, I often question how we come to grips with something that is in a state of constant flux. Flux is a maelstrom of material; its counterpart, flow is the state where comprehension of flux is manageable. Sound art can be considered as being in a state of constant sonic flux, as a force, an energy, which through apprehension and understanding leads to flow. Hence the compositional approach has been one which involves indeterminate procedures, 'free improvisation' and spontaneous expression as reflected in Daoist philosophy. This workflow is rooted in similar practice to martial arts, intuitive aesthetic practices that move between states of flux and flow and which embody Dao.

Published
2019

92. 4-[(Methoxy­glycyl)­carbonyl]­tetra­thia­fulvalene.

Author

Batsanov, Andrei S., Viles, Sarah L., and Moore, Adrian J.

Subjects
*METHOXYETHANOL, *MOLECULAR structure, *ESTERS, *ORGANIC compounds, *CHEMICAL bonds, *HYDROGEN bonding, *MOLECULAR association
Abstract

The title compound, C10H9NO3S4, has a nearly planar tetra­thia­fulvalene–amide moiety and an ester group normal to it. Molecules in the crystal structure are linked by S⋯O interactions and N—H⋯O hydrogen bonds. [ABSTRACT FROM AUTHOR]

Published
2005
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93. Combining high electron affinity and intramolecular charge transfer in 1,3-dithiole-nitrofluorene push-pull diads.

Author

Perepichka DF, Perepichka IF, Ivasenko O, Moore AJ, Bryce MR, Kuz'mina LG, Batsanov AS, and Sokolov NI

Subjects
Crystallography, X-Ray, Electrons, Fluorenes chemical synthesis, Models, Chemical, Models, Molecular, Molecular Structure, Stereoisomerism, Toluene chemistry, Fluorenes chemistry, Toluene analogs & derivatives
Abstract

Attaching electron-rich 1,3-dithiol-2-ylidene moieties to polynitrofluorene electron acceptors leads to the formation of highly conjugated compounds 6 to 11, which combine high electron affinity with a pronounced intramolecular charge transfer (ICT) that is manifested as an intense absorption band in their visible spectra. Such a rare combination of optical and electronic properties is beneficial for several applications in optoelectronics. Thus, incorporation of fluorene-dithiole derivative 6a into photoconductive films affords photothermoplastic storage media with dramatically increased photosensitivity in the ICT region. A wide structural variation of the dithiole and fluorene parts of the molecules reveals excellent correlation between the ICT energy and the reduction potential with the Hammett's parameters for the substituents. Although only a small solvatochromism of the ICT band was observed, heating the solution led to a pronounced blueshift, which was probably as a result of increased twisting around the C9=C14 bond that links the fluorene and dithiole moieties. X-ray crystallographic analysis of 7a, 8a, 10a, 11a and 13a confirms an ICT interaction in the ground state of the molecules. The C9=C14 double bond between the donor and acceptor is substantially elongated and its length increases as the donor character of the dithiole moiety is enhanced.

Published
2008
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