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Molecular Engineering of Nonhalogenated Solution-Processable Bithiazole-Based Electron-Transport Polymeric Semiconductors

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journal contribution
posted on 28.04.2015, 00:00 by Boyi Fu, Cheng-Yin Wang, Bradley D. Rose, Yundi Jiang, Mincheol Chang, Ping-Hsun Chu, Zhibo Yuan, Canek Fuentes-Hernandez, Bernard Kippelen, Jean-Luc Brédas, David M. Collard, Elsa Reichmanis
The electron deficiency and trans-planar conformation of bithiazole is potentially beneficial for the electron-transport performance of organic semiconductors. However, the incorporation of bithiazole into polymers through a facile synthetic strategy remains a challenge. Herein, 2,2′-bithiazole was synthesized in one step and copolymerized with di­thienyl­diketo­pyrrolopyrrole to afford poly­(di­thienyl­diketo­pyrrolopyrrole-bithiazole), PDBTz. PDBTz exhibited electron mobility reaching 0.3 cm2 V–1 s–1 in organic field-effect transistor (OFET) configuration; this contrasts with a recently discussed isoelectronic conjugated polymer comprising an electron-rich bithiophene and dithienyldiketopyrrolopyrrole, which displays merely hole-transport characteristics. This inversion of charge-carrier transport characteristics confirms the significant potential for bithiazole in the development of electron-transport semiconducting materials. Branched 5-decylheptacyl side chains were incorporated into PDBTz to enhance polymer solubility, particularly in nonhalogenated, more environmentally compatible solvents. PDBTz cast from a range of nonhalogenated solvents exhibited film morphologies and field-effect electron mobility similar to those cast from halogenated solvents.

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