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Unsymmetrically Substituted Donor–π–Acceptor‐Type 5,15‐Diazaporphyrin Sensitizers: Synthesis, Optical and Photovoltaic Properties
Author(s) -
Omomo Satoshi,
Tsuji Yukihiro,
Sugiura Kenichi,
Higashino Tomohiro,
Nakano Haruyuki,
Imahori Hiroshi,
Matano Yoshihiro
Publication year - 2017
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201700051
Subject(s) - chromophore , photochemistry , acceptor , dye sensitized solar cell , electrochemistry , energy conversion efficiency , absorption spectroscopy , electron donor , absorption (acoustics) , chemistry , spectroscopy , materials science , optoelectronics , organic chemistry , catalysis , optics , electrode , physics , quantum mechanics , electrolyte , condensed matter physics , composite material
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 TiO 2 ‐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.