Synthesis of Near Infrarad Absorbing Dyes Derived from (Dialkylamino) thiazole Dimers
| Project/Area Number |
11650869
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
有機工業化学
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| Research Institution | Gifu University |
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Principal Investigator |
MATSUI Masaki Faculty of Engineering, Department of Chemistry Gifu University Associate Professor, 工学部, 助教授 (60108058)
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| Project Period (FY) |
1999 – 2000
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| Project Status |
Completed (Fiscal Year 2000)
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| Budget Amount *help |
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2000: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1999: ¥2,700,000 (Direct Cost: ¥2,700,000)
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| Keywords | near infrared absorbing dyes / thiazoles / functional dyes / azo dyes / indamine dyes / solvatochromism / halochromism / chromophoric system / スクアリリウム色素 / クロコニウム色素 |
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| Research Abstract |
Since (dialkylamino) thiazole dimers show very strong electron-donating ability, these compound are interesting materials in dyes chemistry. The synthesis, structure, and UV-Vis absorption spectra of azo and indamine dyes deerived from (dialkylamino) thiazole dimers are examined in this report.
Azo dyes were synthesized by the diazotization of arylamines followed by coupling with (dialkylamino) thiazole dimers in moderate yields. The azo dyes showed 1) the first and second absorption were abserved at 568-737 (ε=24000-88000) and 404-475 (ε=9200-52000) nm, respectively. 2) bithiazolyl moiety was planar and the dihedral angle between the phenyl and bithiazolyl moieties were 8.5 degree, the azo dye being planar. 3) the nagative solvatochromism was observed for azo dyes having very strong electron-withdrawing substituents such as the 4-(perfluoroalkylsulfonyl)- and 2,4-dinitrophenyls.
Indamine dyes were obtained by the reaction of (dialkylamino) thiazole dimers with arylnitroso compounds followed by heating with metal salts in low to moderate yields. Nickel (II) tetrafluoroborate was the best one. 1) the first absorption bands were observed at 648-725 nm (ε=3900-55000), 2) these indamined dyes are found to show intramolecular charge-transfer chromophoric system on the basis of substituent and MO calculation. 3) the near the dihedral angle between the bithiazolyl and arylamino moieties to parpendicular, the more bathochromic the compound, due to increase in the energy level of HOMO.
Thus, (dialkylamino) thiazole dimers are very unique compounds. Azo and indamine dyes prepared in this study showed their first absorption bands in the near infrared reagion. These informations are completely new in the field of dye chemistry.
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Report
(3 results)
Research Products
(6 results)
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[Publications] J.-J.Kim,K.Funabiki,H.Muramatsu,K.Shibata,S.-H.Kim,H.Shiozaki,H.Hartmann,and M.Matsui: "Synthesis, Structure, and Absorption Spectra of Azo Dyes Derived from (Dialkylamino) thiazole Dimers"J.Chem.Soc., Perkin Trans.2,. 379-387 (2001)
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