1. Persulfurated Benzene‐Cored Asterisks with π‐Extended ThioNaphthyl Arms: Synthesis, Structural, Photophysical and Covalent Dynamic Properties
- Author
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Sapna Gahlot, Alessandro Gradone, Myriam Roy, Michel Giorgi, Simone Conti, Paola Ceroni, Marco Villa, Marc Gingras, Centre Interdisciplinaire de Nanoscience de Marseille (CINaM), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS), Department of Chemistry 'Giacomo Ciamician', University of Bologna/Università di Bologna, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Fédération des Sciences Chimiques de Marseille (FRSCM), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR-20-CE07-0031,SulfurDance,'La Danse du Soufre' : Polythioarenes en tant que Plateformes en Chimie Covalente Dynamique(2020), Gahlot, Sapna, Gradone, Alessandro, Roy, Myriam, Giorgi, Michel, Conti, Simone, Ceroni, Paola, Villa, Marco, and Gingras, Marc
- Subjects
[CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry ,materials science ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,sulfur ,Organic Chemistry ,photophysic ,arene ,General Chemistry ,aromatic substitution ,Catalysis ,supramolecular chemistry - Abstract
The synthesis of regioisomeric asterisks (5) and (6) incorporating a benzene core with six 1-naphthylthio or six 2-naphthylthio arms are reported in search for new materials with optoelectronic properties. The consequences on the extension of a pi system surrounding a persulfurated benzene core provide a new avenue to study the structural, photophysical, and chemical properties of such family of all-organic phosphors. It also diverts the persulfuration mechanism after two radical cyclizations for making a [5]dithiohelicene by-product (7) and favors dynamic sulfur component exchange reactions surrounding the core. These exchanges convert asterisks (5) and (6), non-phosphorescent at 20 degrees C to the highly phosphorescent (4) (phi similar to 100 %, solid state at 20 degrees C). For asterisks (5) and (6), the absence of the typical phosphorescence of the per(phenylthio)benzene core in the solid state at 20 degrees C and the presence of a weak naphthalene-based phosphorescence at 77 K is attributed to an energy transfer from the triplet state of the persulfurated benzene core to the outer naphthalene moieties, resulting in an antenna system.
- Published
- 2022
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