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

Accès libre Peer reviewed | |
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Version acceptée pour publication (post-print auteur) | |
Paternité - Pas d'utilisation commerciale [CC] [BY] [NC] | |
Auteurs |
Meera Mohankumar Basab Chattopadhyay Rachid Hadji Lionel Sanguinet Alan R. Kennedy Vincent Lemaur Jérôme Cornil Olivier James Fenwick Paolo Samorì Yves Geerts |
Unité de recherche du site |
Institut de Science et d'Ingénierie Supramoléculaires - ISIS - UMR7006 |
Langue |
en |
Date de première publication |
2018-10-02 |
ISSN |
21926506 |
Titre de la source (revue, livre…) |
ChemPlusChem |
Résumé |
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. Show less |
DOI | 10.1002/cplu.201800346 |
Titre abrégé de la source |
ChemPlusChem |
Type de publication |
ACL |
Domaine |
Chimie/Matériaux |
Unité de recherche extérieure au site |
Laboratoire de Chimie des Polymères Faculté des Sciences; Université Libre de Bruxelles (ULB); 1050 Bruxelles Belgium |
Fonction |
aut |
Identifiant ORCID |
0000-0001-5106-1880 0000-0001-8601-286X 0000-0002-2660-5767 |
Identifiant idREF |
175441898 144461757 076363759 181088452 109288335 |
Audience |
International |
Envoyer vers HAL |
5 |
URL | https://univoak.eu/islandora/object/islandora:71906 |