Oxacycle-Fused [1]Benzothieno[3,2‐b][1]benzothiophene Derivatives: Synthesis, Electronic Structure, Electrochemical Properties, Ionisation Potential, and Crystal Structure

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2018-10-02

21926506

ChemPlusChem

The molecular properties of [1]benzothieno[3,2‐b][1]benzothiophene (BTBT) are vulnerable to structural modifications, which in turn are determined by the functionalization of the backbone. Hence versatile synthetic strategies are needed to discover
Show moreThe molecular properties of [1]benzothieno[3,2‐b][1]benzothiophene (BTBT) are vulnerable to structural modifications, which in turn are determined by the functionalization of the backbone. Hence versatile synthetic strategies are needed to discover the properties of this molecule. To address this, we have attempted heteroatom (oxygen) functionalization of BTBT by a concise and easily scalable synthesis. Fourfold hydroxy‐substituted BTBT is the key intermediate, from which the compounds 2,3,7,8‐bis(ethylenedioxy)‐[1]benzothieno[3,2‐b][1]benzothiophene and 2,3,7,8‐bis(methylenedioxy)‐[1]benzothieno[3,2‐b][1]benzothiophene are synthesized. The difference in ether functionalities on the BTBT scaffold influences the ionisation potential values substantially. The crystal structure reveals the transformation of the herringbone motif in bare BTBT towards π‐stacked columns in the newly synthesized derivatives. The results are further justified by the simulated HOMO levels of the model compound.
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ChemPlusChem

ACL

Chimie/Matériaux

Laboratoire de Chimie des Polymères Faculté des Sciences; Université Libre de Bruxelles (ULB); 1050 Bruxelles Belgium
LUNAM Université MOLTECH-Anjou UMRCNRS 6200; Université d'Angers; 2 Bd Lavoisier 49045 Angers Cedex France
Department of Pure and Applied Chemistry; University of Strathclyde; 295 Cathedral Street Glasgow G1 1XL Scotland, UK
Service de Chimie des Matériaux Nouveaux; Université de Mons (UMons); Place du Parc 20 7000 Mons Belgium

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International

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