Molecular engineering of nonhalogenated solution-processable bithiazole-based electron-transport polymeric semiconductors

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

Research output: Contribution to journalArticlepeer-review

72 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 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.

Original languageEnglish (US)
Pages (from-to)2928-2937
Number of pages10
JournalChemistry of Materials
Volume27
Issue number8
DOIs
StatePublished - Apr 28 2015
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

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