Syntheses of Near Infrared Absorbing Dyes
Project/Area Number |
01550664
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Research Category |
Grant-in-Aid for General Scientific Research (C)
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Allocation Type | Single-year Grants |
Research Field |
Synthetic chemistry
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Research Institution | Fukui University |
Principal Investigator |
KITAJIMA Hidehiko Fukui University, Faculty of Engineering, Department of Applied Chemistry and Biotechnology, Prof., 工学部・生物化学工学科, 教授 (50020186)
|
Co-Investigator(Kenkyū-buntansha) |
KEUMI Takashi Fukui University, Faculty of Engineering, Department of Applied Chemistry and Bi, 工学部生物化学工学科, 助教授 (10020215)
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Project Period (FY) |
1989 – 1990
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Project Status |
Completed (Fiscal Year 1990)
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Budget Amount *help |
¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1990: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1989: ¥1,500,000 (Direct Cost: ¥1,500,000)
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Keywords | Near Infrared Absorbing Dyes / Phenanthren-I, 4-Dione / Diels-Alder Reaction / Regioselectivity / MNDO MO / PPP-CI MO / フェナントレン1,4ージオン / DielsーAlder反応 / 深色シフト / 1,4-フェナントラキノン / PPP-MO |
Research Abstract |
Near infrared absorbing dyes have attracted considerable attention, since these organic dyes have prospect of many applications in the field of diode-laser optical storage. However, organic dyes which can absorb at near infrared light are not numerous and earnestly desired. In this study, the new deep-colored 6-dialkylaminophenanthren-1, 4-dione dyes 5a-5t were synthesized. 5 were prepared as follows : p-Benzoquinone derivatives 1 reacted with p-di-alkylaminostyrenes 2 in dioxane under reflux or at room temperature. 1-(p-dialkylaminopheny1)-ethanol 3 or 1-(p-dialkylaminophenyl) ethyl acetate 4 were employed as alternatives of styrene derivatives 2. The reactions proceeded via DielsーAlder reaction of 1 and 2, followed aromatization by 1 or 2. The regioselectivity of the reaction was explained by MNDO-MO calculations. The visible absorption band data of 5 in chloroform are summarized in Table. Chlorine atom substitutions in the 2 and 3 positions of 5a-5c produced bathochromic displacements of lambdamax (ca. 60nm). The absorption bands of 5a-5i examined by the PPP-CI MO calculations with variable beta approximation. The calculated lambda of these dyes were in agreement with the experimental data. Syntheses of 2, 3-dicyano derivatives of 5a-5c are in progress.
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Report
(3 results)
Research Products
(4 results)