Unsymmetrically Substituted Donor–π–Acceptor-Type 5,15-Diazaporphyrin Sensitizers: Synthesis, Optical and Photovoltaic Properties

Satoshi Omomo, Yukihiro Tsuji, Kenichi Sugiura, Tomohiro Higashino, Haruyuki Nakano, Hiroshi Imahori, Yoshihiro Matano

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The first examples of unsymmetrical β-substituted donor–π–acceptor (D–π–A)-type 5,15-diazaporphyrin (DAP) sensitizers with both p-aminophenyl and p-carboxyphenyl groups at their peripheral 3-, 7-, 13-, and/or 17-positions have been synthesized for use in dye-sensitized solar cells (DSSCs). UV/Vis absorption and emission spectroscopy, electrochemical measurements, and DFT calculations revealed that these D–π–A dyes exhibit high light-harvesting properties over the whole visible range because of the intrinsic charge-transfer character of their electronic transitions. The cell performances of TiO2-based DSSCs fabricated with the newly prepared DAP derivatives were evaluated under standard AM1.5 conditions. Among the four dyes examined, 13,17-bis(p-carboxyphenyl)-3,7-bis[p-(N,N-dimethylamino)phenyl]-DAP showed the highest power conversion efficiency (2.0 %), which was 20 times larger than that obtained with 3-(p-carboxyphenyl)-DAP. These results show that the DAP chromophore could be used as the electron-accepting π unit in various types of functional dyes.

Original languageEnglish
Pages (from-to)695-704
Number of pages10
JournalChemPlusChem
Volume82
Issue number5
DOIs
Publication statusPublished - May 1 2017

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Coloring Agents
Emission spectroscopy
Chromophores
Ultraviolet spectroscopy
Absorption spectroscopy
Discrete Fourier transforms
Conversion efficiency
Charge transfer
Derivatives
Electrons
Dye-sensitized solar cells

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Unsymmetrically Substituted Donor–π–Acceptor-Type 5,15-Diazaporphyrin Sensitizers : Synthesis, Optical and Photovoltaic Properties. / Omomo, Satoshi; Tsuji, Yukihiro; Sugiura, Kenichi; Higashino, Tomohiro; Nakano, Haruyuki; Imahori, Hiroshi; Matano, Yoshihiro.

In: ChemPlusChem, Vol. 82, No. 5, 01.05.2017, p. 695-704.

Research output: Contribution to journalArticle

Omomo, Satoshi ; Tsuji, Yukihiro ; Sugiura, Kenichi ; Higashino, Tomohiro ; Nakano, Haruyuki ; Imahori, Hiroshi ; Matano, Yoshihiro. / Unsymmetrically Substituted Donor–π–Acceptor-Type 5,15-Diazaporphyrin Sensitizers : Synthesis, Optical and Photovoltaic Properties. In: ChemPlusChem. 2017 ; Vol. 82, No. 5. pp. 695-704.
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