Efficient routes towards a series of 5,5′-bithiazolidinylidenes as π-electron acceptors

Autor: Nathalie Bellec, D. Ameline, Antoine Vacher, Thierry Roisnel, Y. Le Gal, Olivier Jeannin, Dominique Lorcy, Vincent Dorcet
Přispěvatelé: 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), 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)
Rok vydání: 2015
Předmět:
Zdroj: Organic and Biomolecular Chemistry
Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2015, 13 (31), pp.8479--8486. ⟨10.1039/C5OB01169H⟩
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry, 2015, 13 (31), pp.8479--8486. ⟨10.1039/C5OB01169H⟩
ISSN: 1477-0539
1477-0520
Popis: International audience; Different approaches have been studied in order to prepare efficiently the sulfur rich electron acceptor, DEBTTT. Among the various routes used, the one going through the synthesis of a bicyclic derivative, where the thiazole-2-chalcogenone is fused with a 1,3-dithiole-2-one, leads to the target molecule under milder conditions and better yield. Thus, this approach has been explored for the synthesis of a series of acceptors either by modifying the substituent on the thiazole core or by changing the exocyclic chalcogen atoms. All these sulfur rich electron acceptors exhibit short intra- and intermolecular SS contacts in the solid state. Electrochemical investigations show that the nature of the exocyclic chalcogen atom of the thiazole ring has a significant influence on the accepting ability as a cathodic shift of about 220 mV is observed just by changing sulfur for oxygen. This structural modification enables the tuning of the redox properties.
Databáze: OpenAIRE
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