Molecular Engineering of Non-Halogenated Solution-Processable Bithiazole based Electron Transport Polymeric Semiconductors

Boyi Fu, Cheng-Yin Wang, Bradley Daniel Rose, Yundi Jiang, Mincheol Chang, Ping-Hsun Chu, Zhibo Yuan, Canek Fuentes-Hernandez, Kippelen Bernard, Jean-Luc Bredas, David M. Collard, Elsa Reichmanis

Research output: Contribution to journalArticlepeer-review

70 Scopus citations

Abstract

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 cm2V-1s-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 non-halogenated, more environmentally compatible solvents. PDBTz cast from a range of non-halogenated solvents exhibited film morphologies and field-effect electron mobility similar to those cast from halogenated solvents.
Original languageEnglish (US)
Pages (from-to)2928-2937
Number of pages10
JournalChemistry of Materials
Volume27
Issue number8
DOIs
StatePublished - Apr 13 2015

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