Journal
JOURNAL OF PHOTOPOLYMER SCIENCE AND TECHNOLOGY
Volume 30, Issue 5, Pages 561-568Publisher
TECHNICAL ASSOC PHOTOPOLYMERS,JAPAN
DOI: 10.2494/photopolymer.30.561
Keywords
Benzothiadiazole; Acceptor unit; Ring-fusion; Thiazole; Imidazole
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Funding
- Center of Innovation Program (COI)
- Advanced Low Carbon Technology R&D Program (ALCA) from Japan Science and Technology Agency, JST
- Low Carbon Technology Research and Development Program from Ministry of the Environment
- JSPS KAKENHI [JP26288093]
- JSPS
- Grants-in-Aid for Scientific Research [17J10525] Funding Source: KAKEN
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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.
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