Design, synthesis, chemical stability, packing, cyclic voltammetry, ionisation potential, and charge transport of [1]benzothieno[3,2-b][1]benzothiophene derivatives

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RUZIÉ, Christian, KARPINSKA, Jolanta, LAURENT, Anne, SANGUINET, Lionel, HUNTER, Simon, ANTHOPOULOS, Thomas D., LEMAUR, Vincent, CORNIL, Jérôme, KENNEDY, Alan R., FENWICK, Olivier James, SAMORÌ, Paolo, SCHWEICHER, Guillaume, CHATTOPADHYAY, Basab et GEERTS, Yves Henri, sans date. Design, synthesis, chemical stability, packing, cyclic voltammetry, ionisation potential, and charge transport of [1]benzothieno[3,2-b][1]benzothiophene derivatives. Journal of Materials Chemistry C. sans date. Vol. 4, n° 22pp. 4863-4879. DOI 10.1039/C6TC01409G. 1. .
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Version acceptée pour publication (post-print auteur)
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Auteurs Christian Ruzié
Jolanta Karpinska
Anne Laurent
Lionel Sanguinet
Simon Hunter
Thomas D. Anthopoulos
Vincent Lemaur
Jérôme Cornil
Alan R. Kennedy
Olivier James Fenwick
Paolo Samorì
Guillaume Schweicher
Basab Chattopadhyay
Yves Henri Geerts
Unité de recherche du site Institut de Science et d'Ingénierie Supramoléculaires - ISIS - UMR7006
Langue

en
Volume

4
Numéro

22
Page de début

4863
Page de fin

4879
Date de première publication

2016-05-05
ISSN

2050-7526
2050-7534
Titre de la source (revue, livre…)

Journal of Materials Chemistry C
Résumé

Five new molecular semiconductors that differ from dioctylbenzothienobenzothiophene, by the introduction of ether or thioether side chains, have been synthesized and obtained in good yields. Their availability in sufficient quantities has allowed Show moreFive new molecular semiconductors that differ from dioctylbenzothienobenzothiophene, by the introduction of ether or thioether side chains, have been synthesized and obtained in good yields. Their availability in sufficient quantities has allowed investigation of their electrochemical behaviour in solution and their electronic properties in solid state. Both ether and thioether compounds oxidise rather easily in solution, but nevertheless, they exhibit rather high ionisation potentials. This is a consequence of their crystal structure. Dioctylthioetherbenzothienobenzothiophene is rather sensitive to oxidation and degrades easily in close to ambient conditions. Dioctyletherbenzothienobenzothiophene is more stable. Its charge carrier mobility remains however rather moderate, on the order of 0.5 cm2 V−1 s−1, whereas that of dioctylbenzothienobenzothiophene reached 4 cm2 V−1 s−1, in the same conditions. The difference is explained by intrinsic factors as shown by a theoretical modelling. Show less
DOI 10.1039/C6TC01409G
Titre abrégé de la source

J. Mater. Chem. C
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), CP 206/1, Boulevard du Triomphe, 1050 Bruxelles, Belgium
LUNAM Université, MOLTECH-Anjou UMRCNRS 6200, Université d'Angers, 2 Bd Lavoisier, 49045 Angers Cedex, France
Department of Physics and Centre for Plastic Electronics, Imperial College London, South Kensington, UK
Service de Chimie des Matériaux Nouveaux, Université de Mons (UMons), Place du Parc 20, 7000 Mons, Belgium
Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland
Fonction

aut
Audience

International
Envoyer vers HAL

5
URL https://univoak.eu/islandora/object/islandora:72565