| Project/Area Number |
61550641
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Kochi University |
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Principal Investigator |
YOSHIDA Katsuhira Faculty of Science, Kochi University, Associate Professor, 理学部, 助教授 (30036595)
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| Project Period (FY) |
1986 – 1987
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| Project Status |
Completed (Fiscal Year 1987)
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| Budget Amount *help |
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1987: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1986: ¥1,500,000 (Direct Cost: ¥1,500,000)
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| Keywords | Arthraquinone derivatives / 5,8-Quinolinedione derivatives / 1,2-Naphtoquinone derivatives / Functional dyes / Amination / Arylation / 近赤外吸収色素 / アントラキノン誘導体 / 5,8-キノリンジオン誘導体 / アミノ化 / アリール化 / 金属キレート / 光アミノ化 / 光ヒドロキシル化 |
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| Research Abstract |
New syntheses of various quinone derivatives promoted by metal chelate formation and functional properties of the quinones have been investigated. The results are summarized as follows:
1. The reaction of some diamino- and dihydroxy-anthraquinones with alkylamines was examined in the presence of metal salts. The alkylamino groups were directly introduced into the anthraquinone nucleus to afford various aminoanthraquinone derivatives.
2. The reaction of 5,8-quinolinedione with various amines was strongly promoted by some metal ions to give regioselectively the 6-aminated and/or the 6-arylated products.
3. The reaction of 1,2-naphthoquinones with various amines was also promoted by some metal ions to give regioselectively the 4-aminated and/or 4-arylated products.
4. Among the quinone dervatives obtained by the above reactions, many compounds showed chromotropic properties. For example, 4-arylamino-1,2-naphthoquinones showed a clear solvatochromism induced by the quinone-quinoneimine tautomerism. The 6-substituent-5,8-quinolinediones and 4-substituent-1,2-naphthoquinones showed a metalochromism with a large bathochromic shift for the metal chelate complexation and showed a strong absorption maximum in the near infrared reagion. These compounds are expected to be used as metal ion indicators, optical filters, or new near infrared absorbing dyes.
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