Donor-acceptor alternating copolymer based on thermally converted isothianaphthene dimer and thiazolothiazole subunits

Tomokazu Umeyama, Kohei Hirose, Kei Noda, Kazumi Matsushige, Tetsuya Shishido, Hanna Saarenpää, Nikolai V. Tkachenko, Helge Lemmetyinen, Noboru Ono, Hiroshi Imahori

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10 Citations (Scopus)

Abstract

A novel donor-acceptor-conjugated polymer PBITT consisting of isothianaphthene (ITN) dimer donor unit and thiazolothiazole acceptor unit was synthesized by thermal conversion method. First, a soluble precursor polymer with an alternating main chain structure of bicyclo[2.2.2]octadiene (BCOD)-fused thiophene dimer and benzodithiophene (PPBITT) was synthesized by palladium(0)-catalyzed Stille coupling reaction. The BCOD moiety underwent the retro-Diels-Alder reaction by the thermal treatment of a red PPBITT film to afford a dark blue film of PBITT that was insoluble in any organic solvents. The optical bandgap of PBITT (1.3 eV) became significantly narrow compared with that of PPBITT (2.1 eV) due to the stabilized quinoid resonance structure of the PBITT main chain. The field-effect hole mobility (μ h) of PBITT was determined to be 2.2 × 10 -4 cm 2 V -1 s -1 with on-off ratio (I on/I off) of 2.5 × 10 2, whereas the corresponding PPBITT-based device did not show any p- and n-type response. Organic photovoltaic (OPV) devices were fabricated based on the bulk heterojunction film of the polymers and [6,6]-phenyl-C 61-butyric acid methyl ester (PCBM). The device with the PBITT:PCBM film exhibited higher short-circuit current and lower open-circuit voltage than those of the PPBITT:PCBM-based device, resulting in the comparable power conversion efficiency (∼0.3%). These results obtained here will provide fundamental information on the design of thermally induced donor-acceptor alternating polymers for organic electronics.

Original languageEnglish
Pages (from-to)17414-17423
Number of pages10
JournalJournal of Physical Chemistry C
Volume116
Issue number33
DOIs
Publication statusPublished - 2012 Aug 23
Externally publishedYes

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Energy(all)
  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films

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    Umeyama, T., Hirose, K., Noda, K., Matsushige, K., Shishido, T., Saarenpää, H., Tkachenko, N. V., Lemmetyinen, H., Ono, N., & Imahori, H. (2012). Donor-acceptor alternating copolymer based on thermally converted isothianaphthene dimer and thiazolothiazole subunits. Journal of Physical Chemistry C, 116(33), 17414-17423. https://doi.org/10.1021/jp305001p