Synthesis of Azole-fused Benzothiadiazoles as Key Units for Functional π-Conjugated Compounds

2,1,3-Benzothiadiazole (BT) is a widely used electron-accepting unit in organic electronics including organic solar cells (OSCs). As modifications of BT skeleton, two types of azole-fused BT units were designed and synthesized; thiazole-fused BT with an electron-withdrawing C=N bond and imidazole-fu...

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Bibliographic Details
Published in:Journal of Photopolymer Science and Technology 2017/06/26, Vol.30(5), pp.561-568
Main Authors: Nakamura, Tomoya, Okazaki, Shuhei, Arakawa, Noriko, Satou, Motoi, Endo, Masaru, Murata, Yasujiro, Wakamiya, Atsushi
Format: Article
Language:English
Subjects:
Acceptor unit
Benzothiadiazole
Electronic structure
Imidazole
Nitrogen
Oxidation
Photovoltaic cells
Ring-fusion
Solar cells
Sulfur
Thiazole
Valence
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Summary:2,1,3-Benzothiadiazole (BT) is a widely used electron-accepting unit in organic electronics including organic solar cells (OSCs). As modifications of BT skeleton, two types of azole-fused BT units were designed and synthesized; thiazole-fused BT with an electron-withdrawing C=N bond and imidazole-fused BT with an electron-donating nitrogen atom as well as an electron-withdrawing C=N bond. Electrochemical measurements and theoretical calculations suggest that thiazole-fusion enhances the electron-accepting ability, whereas imidazole-fusion endows the BT skeleton with electron-donating ability while maintaining its electron-accepting ability. Moreover, in thiazole-fused BT units, the electronic structure could be further modulated by varying the oxidation state of the sulfur atom in methylthio group at the fused thiazole ring.
ISSN:0914-9244
1349-6336
DOI:10.2494/photopolymer.30.561