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Int. J. Mol. Sci. 2017, 18(2), 427; doi:10.3390/ijms18020427

Synthesis of 8-Aryl-O-methylcyanidins and Their Usage for Dye-Sensitized Solar Cell Devices

1
Graduate School of Information Science, Nagoya University, Chikusa, Nagoya 464-8601, Japan
2
Chemical Instrumentation Facility, Research Center for Materials Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
3
Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
*
Author to whom correspondence should be addressed.
Academic Editors: Nuno Mateus, Iva Fernandes and Maurizio Battino
Received: 24 December 2016 / Revised: 3 February 2017 / Accepted: 9 February 2017 / Published: 16 February 2017
(This article belongs to the Special Issue Anthocyanins)
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Abstract

Anthocyanins as natural pigments are colorful and environmentally compatible dyes for dye-sensitized solar cells (DSSCs). To increase the efficiency, we designed and synthesized unnatural O-methylflavonols and O-methylcyanidins that possess an aryl group at the 8-position. We synthesized per-O-methylquercetin from quercetin, then using selective demethylation prepared various O-methylquercetins. Using the Suzuki-Miyaura coupling reaction, 8-arylation of per-O-methylquercetin was achieved. Using a LiAlH4 reduction or Clemmensen reduction, these flavonols were transformed to the corresponding cyanidin derivatives in satisfactory yields. Using these dyes, we fabricated DSSCs, and their efficiency was investigated. The efficiency of tetra-O-methylflavonol was 0.31%. However, the introduction of the 8-aryl residue increased the efficiency to 1.04%. In comparison to these flavonols, O-methylcyanidins exhibited a lower efficiency of 0.05% to 0.52%. The introduction of the 8-aryl group into the cyanidin derivatives did not result in a remarkable increase in the efficiency. These phenomena may be due to the poor fit of the HOMO-LUMO level of the dyes to the TiO2 conduction band. View Full-Text
Keywords: 8-aryl-O-methylcyanidin; 8-aryl-O-methylquercetin; dye-sensitized solar cells; O-methylcyanidin; O-methylquercetin 8-aryl-O-methylcyanidin; 8-aryl-O-methylquercetin; dye-sensitized solar cells; O-methylcyanidin; O-methylquercetin
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Kimura, Y.; Oyama, K.-I.; Murata, Y.; Wakamiya, A.; Yoshida, K. Synthesis of 8-Aryl-O-methylcyanidins and Their Usage for Dye-Sensitized Solar Cell Devices. Int. J. Mol. Sci. 2017, 18, 427.

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