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

Research output: Contribution to journalArticle

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

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Dimers
Butyric acid
Butyric Acid
butyric acid
copolymers
Copolymers
dimers
esters
Esters
Polymers
polymers
Thiophenes
Diels-Alder reactions
Hole mobility
Conjugated polymers
Optical band gaps
hole mobility
Palladium
Thiophene
Open circuit voltage

ASJC Scopus subject areas

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

Cite this

Donor-acceptor alternating copolymer based on thermally converted isothianaphthene dimer and thiazolothiazole subunits. / Umeyama, Tomokazu; Hirose, Kohei; Noda, Kei; Matsushige, Kazumi; Shishido, Tetsuya; Saarenpää, Hanna; Tkachenko, Nikolai V.; Lemmetyinen, Helge; Ono, Noboru; Imahori, Hiroshi.

In: Journal of Physical Chemistry C, Vol. 116, No. 33, 23.08.2012, p. 17414-17423.

Research output: Contribution to journalArticle

Umeyama, T, Hirose, K, Noda, K, Matsushige, K, Shishido, T, Saarenpää, H, Tkachenko, NV, 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, vol. 116, no. 33, pp. 17414-17423. https://doi.org/10.1021/jp305001p
Umeyama, Tomokazu ; Hirose, Kohei ; Noda, Kei ; Matsushige, Kazumi ; Shishido, Tetsuya ; Saarenpää, Hanna ; Tkachenko, Nikolai V. ; Lemmetyinen, Helge ; Ono, Noboru ; Imahori, Hiroshi. / Donor-acceptor alternating copolymer based on thermally converted isothianaphthene dimer and thiazolothiazole subunits. In: Journal of Physical Chemistry C. 2012 ; Vol. 116, No. 33. pp. 17414-17423.
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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.",
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AU - Noda, Kei

AU - Matsushige, Kazumi

AU - Shishido, Tetsuya

AU - Saarenpää, Hanna

AU - Tkachenko, Nikolai V.

AU - Lemmetyinen, Helge

AU - Ono, Noboru

AU - Imahori, Hiroshi

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