title: Efficient routes towards a series of 5,5'-bithiazolidinylidenes as π-electron acceptors.
abstract: 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.
authors.affiliation: Institut des Sciences Chimiques de Rennes - UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, Bât 10A, 35042 Rennes Cedex, France. Dominique.lorcy@univ-rennes1.fr.
authors.forename: Y
authors.initials: Y
authors.lastname: Le Gal
authors.forename: D
authors.initials: D
authors.lastname: Ameline
authors.forename: N
authors.initials: N
authors.lastname: Bellec
authors.forename: A
authors.initials: A
authors.lastname: Vacher
authors.forename: T
authors.initials: T
authors.lastname: Roisnel
authors.forename: V
authors.initials: V
authors.lastname: Dorcet
authors.forename: O
authors.initials: O
authors.lastname: Jeannin
authors.forename: D
authors.initials: D
authors.lastname: Lorcy