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タイトル: | Synthesis of 8-Aryl-O-methylcyanidins and Their Usage for Dye-Sensitized Solar Cell Devices |
著者: | Kimura, Yuki Oyama, Kin-ichi Murata, Yasujiro https://orcid.org/0000-0003-0287-0299 (unconfirmed) Wakamiya, Atsushi https://orcid.org/0000-0003-1430-0947 (unconfirmed) Yoshida, Kumi |
著者名の別形: | 村田, 靖次郎 若宮, 淳志 |
キーワード: | Physical and Theoretical Chemistry Inorganic Chemistry Organic Chemistry Spectroscopy Molecular Biology Catalysis Computer Science Applications |
発行日: | 16-Feb-2017 |
出版者: | MDPI AG |
誌名: | International Journal of Molecular Sciences |
巻: | 18 |
号: | 2 |
論文番号: | 427 |
抄録: | 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. |
著作権等: | © 2017 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/). |
URI: | http://hdl.handle.net/2433/218629 |
DOI(出版社版): | 10.3390/ijms18020427 |
PubMed ID: | 28212330 |
出現コレクション: | 学術雑誌掲載論文等 |
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