Intramolecular Donor–Acceptor Regioregular Poly(3-hexylthiophene)s Presenting Octylphenanthrenyl-Imidazole Moieties Exhibit Enhanced Charge Transfer for Heterojunction Solar Cell Applications

Authors

  • Yao-Te Chang,

    1. Department of Materials Science and Engineering, National Chiao, Tung University 1001 Ta Hsueh Road, Hsinchu, 30049 (Taiwan ROC)
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  • So-Lin Hsu,

    1. Department of Materials Science and Engineering, National Chiao, Tung University 1001 Ta Hsueh Road, Hsinchu, 30049 (Taiwan ROC)
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  • Guan-Yu Chen,

    1. Department of Materials Science and Engineering, National Chiao, Tung University 1001 Ta Hsueh Road, Hsinchu, 30049 (Taiwan ROC)
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  • Ming-Hsin Su,

    1. Department of Materials Science and Engineering, National Chiao, Tung University 1001 Ta Hsueh Road, Hsinchu, 30049 (Taiwan ROC)
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  • Thounaojam Avinash Singh,

    1. Department of Applied Chemistry and Institute of Molecular Science, National Chiao Tung University, 1001 Ta Hsueh Road, Hsinchu, 30049 (Taiwan ROC)
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  • Eric Wei-Guang Diau,

    1. Department of Applied Chemistry and Institute of Molecular Science, National Chiao Tung University, 1001 Ta Hsueh Road, Hsinchu, 30049 (Taiwan ROC)
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  • Kung-Hwa Wei

    Corresponding author
    1. Department of Materials Science and Engineering, National Chiao, Tung University 1001 Ta Hsueh Road, Hsinchu, 30049 (Taiwan ROC)
    • Department of Materials Science and Engineering, National Chiao, Tung University 1001 Ta Hsueh Road, Hsinchu, 30049 (Taiwan ROC).
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  • We are grateful for financial support provided by the National Science Council through Project NSC 95-2120-M-009-007. We thank Hsu-Shen Wang for assistance with the synthesis of devices and Chen-Chia Chen for assistance with the study of devices discussed in this paper. Supporting Information is available online from Wiley InterScience or from the author.

Abstract

Intramolecular donor–acceptor structures prepared by covalently binding conjugated octylphenanthrenyl-imidazole moieties onto the side chains of regioregular poly(3-hexylthiophene)s exhibit lowered bandgaps and enhanced electron transfer compared to the parent polymer, e.g., conjugation of 90 mol% octylphenanthrenyl-imidazole moieties onto poly(3-hexylthiophene) chains reduces the optical bandgap from 1.91 to 1.80 eV, and the electron transfer probability is at least twice as high as that of pure poly(3-hexylthiophene) when blended with [6,6]-phenyl-C61-butyric acid methyl ester. The lowered bandgap and the fast charge transfer both contribute to much higher external quantum efficiencies, thus much higher short-circuit current densities for copolymers presenting octylphenanthrenyl-imidazole moieties, relative to those of pure poly(3-hexylthiophene)s. The short-circuit current density of a device prepared from a copolymer presenting 90 mol% octylphenanthrenyl-imidazole moieties is 13.7 mA · cm−2 which is an increase of 65% compared to the 8.3 mA · cm−2 observable for a device containing pure poly(3-hexylthiophene). The maximum power conversion efficiency of this particular copolymer is 3.45% which suggest that such copolymers are promising polymeric photovoltaic materials.

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