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Triarylamine-Substituted Imidazole- and Quinoxaline-Fused Push–Pull Porphyrins for Dye-Sensitized Solar Cells

  1. Dr. Hironobu Hayashi1,
  2. Dr. Abeda Sultana Touchy2,
  3. Yuriko Kinjo1,
  4. Prof. Kei Kurotobi2,
  5. Yuuki Toude1,
  6. Prof. Seigo Ito3,
  7. Hanna Saarenpää4,
  8. Prof. Nikolai V. Tkachenko4,
  9. Prof. Helge Lemmetyinen4,
  10. Prof. Hiroshi Imahori1,2,*

Article first published online: 11 FEB 2013

DOI: 10.1002/cssc.201200869

Issue

ChemSusChem

ChemSusChem

Volume 6, Issue 3, pages 508–517, March 2013

Additional Information

How to Cite

Hayashi, H., Touchy, A. S., Kinjo, Y., Kurotobi, K., Toude, Y., Ito, S., Saarenpää, H., Tkachenko, N. V., Lemmetyinen, H. and Imahori, H. (2013), Triarylamine-Substituted Imidazole- and Quinoxaline-Fused Push–Pull Porphyrins for Dye-Sensitized Solar Cells. ChemSusChem, 6: 508–517. doi: 10.1002/cssc.201200869

Author Information

  1. 1

    Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510 (Japan)

  2. 2

    Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University, Nishikyo-ku, Kyoto 615-8510 (Japan), Fax: (+81) 75-383-2571

  3. 3

    Department of Electrical Engineering and Computer Sciences, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280 (Japan)

  4. 4

    Department of Chemistry and Bioengineering, Tampere University of Technology, P.O. Box 541, FIN-33101 Tampere (Finland)

*Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510 (Japan)

Publication History

  1. Issue published online: 4 MAR 2013
  2. Article first published online: 11 FEB 2013
  3. Manuscript Received: 14 NOV 2012

Funded by

  • MEXT. Grant Number: 21350100
  • Strategic Japanese-Finnish Cooperative Program
  • Advanced Low Carbon Technology Research and Development Program
  • WPI Initiative
  • JSPS
  • Academy of Finland

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Keywords:

  • dyes/pigments;
  • electrochemistry;
  • porphyrinoids;
  • sustainable chemistry;
  • synthesis design

Abstract

We have prepared a push–pull porphyrin with an electron-donating triarylamino group at the β,β′-edge through a fused imidazole group and an electron-withdrawing carboxyquinoxalino anchoring group at the opposite β,β′-edge (ZnPQI) and evaluated the effects of the push–pull structure of ZnPQI on optical, electrochemical, and photovoltaic properties. ZnPQI showed red-shifted Soret and Q bands relative to a reference porphyrin with only an electron-withdrawing group (ZnPQ), thus demonstrating the improved light-harvesting property of ZnPQI. The optical HOMO–LUMO gap was consistent with that estimated by DFT calculations. The ZnPQI-sensitized solar cell exhibited a relatively high power conversion efficiency (η) of 6.8 %, which is larger than that of the ZnPQ-sensitized solar cell (η=6.3 %) under optimized conditions. The short-circuit current and fill factor of the ZnPQI-sensitized solar cell are larger than those of the ZnPQ-sensitized solar cell, whereas the open circuit potential of the ZnPQI-sensitized cell is smaller than that of the ZnPQ-sensitized cell, leading to an overall improved cell performance of ZnPQI. Such fundamental information provides a new tool for the rational molecular design of highly efficient dye-sensitized solar cells based on push–pull porphyrins.

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