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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.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01188237
Contributor : Laurent Jonchère <>
Submitted on : Friday, August 28, 2015 - 4:26:15 PM
Last modification on : Friday, July 10, 2020 - 4:24:48 PM

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Y. Le Gal, D. Ameline, N. Bellec, A. Vacher, T. Roisnel, et al.. Efficient routes towards a series of 5,5'-bithiazolidinylidenes as π-electron acceptors. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2015, 13 (31), pp.8479--8486. ⟨10.1039/C5OB01169H⟩. ⟨hal-01188237⟩

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