Near infrared absorbing soluble poly(cyclopenta[2,1-b:3,4-b′] dithiophen-4-one)vinylene polymers exhibiting high hole and electron mobilities in ambient air

Zhuping Fei, Xiang Gao, Jeremy Smith, Pichaya Pattanasattayavong, Ester Buchaca Domingo, Natalie Stingelin, Scott E. Watkins, Thomas Anthopoulos, R. Joseph Kline, Martin Heeney*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

We report the synthesis of two novel cyclopenta[2,1-b:3,4-b′] dithiophen-4-one monomers containing solubilizing alkyl groups in the peripheral 3,5 positions. Polymerization with (E)-1,2-bis(tributylstannyl)-ethylene under Stille coupling conditions afforded the first reported examples of soluble poly(cyclopentadithiophen-4-one)vinylenes. The resulting polymers absorb in the near-infrared, with a maximum thin film absorbance around 815 nm and have optical band gaps of 1.25 eV. The polymers exhibit promising ambipolar field effect transistor performance, with average saturated mobilities of 0.5 cm 2 V-1 s-1 for holes and 0.12 cm 2V-1 s-1 for electrons. The ambipolar transistors operate in both the hole and electron transport regimes in ambient air. Prolonged exposure to ambient atmosphere leads to a gradual loss of the electron transport behavior, with little change observed in the p-type mobility.

Original languageEnglish (US)
Pages (from-to)59-68
Number of pages10
JournalChemistry of Materials
Volume25
Issue number1
DOIs
StatePublished - Jan 8 2013

Keywords

  • conjugated polymers
  • low band gap polymer
  • near-infrared absorbers
  • polymer field effect transistors
  • structure-property relationships

ASJC Scopus subject areas

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

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