Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
BCSJ Award Article
Simple Oligothiophene-Based Dyes for Dye-Sensitized Solar Cells (DSSCs): Anchoring Group Effects on Molecular Properties and Solar Cell Performance
Eigo MiyazakiTakashi OkanishiYuki SuzukiNozomi IshineHiroki MoriKazuo TakimiyaYutaka Harima
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2011 Volume 84 Issue 5 Pages 459-465


Simple oligothiophene-based dyes with a cyanoacrylic acid anchor were synthesized and evaluated as a photosensitizer for dye-sensitized solar cells (DSSCs). Although the molecular properties of the dyes at a glance are quite similar to those of related oligothiophene dyes with a carboxylic acid anchor, the DSSC performance of the former (up to η = 4.8%) is fairly improved over the latter (≈1.2%). Absorption spectra of the oligothiophene dyes with the cyanoacrylic acid are red-shifted compared to those with the carboxylic acid, resulting in the improved photocurrent conversion efficiency at above 600 nm in the DSSCs. With the aid of theoretical calculations, electronic properties of the oligothiophene dyes were investigated, and it turned out that the excited states of the dyes are significantly affected by the anchoring groups. The cyanoacrylic acid anchor brings about a stabilized LUMO with localized electron density on the cyanoacrylic acid moiety, whereas the carboxylic acid dye has relatively a high-lying LUMO with delocalized electron density over the oligothiophene moiety. Thus, the difference in the DSSC performance is rationalized by the different electronic structure at the excited states caused by the anchoring groups on the oligothiophene cores.

Oligothiophenes with a cyanoacrylic acid moiety were synthesized, and their DSSCs show power-to-conversion of 2.9–4.8%. Fullsize Image
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© 2011 The Chemical Society of Japan
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