Improvement of Fluorescence Characteristics of Coumarins: Syntheses and Fluorescence Properties of 6-Methoxycoumarin and Benzocoumarin Derivatives as Novel Fluorophores Emitting in the Longer Wavelength Region and Their Application to Analytical Reagents
| Autor: | Toshinobu Masuda, Chiyomi Murata, Hitoshi Nohta, Hideyuki Yoshida, Masatoshi Yamaguchi, Akira Takadate, Yasuko Kamochi, Kenichiro Todoroki |
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| Rok vydání: | 2005 |
| Předmět: |
General Chemistry
General Medicine Conjugated system Photochemistry Fluorescence symbols.namesake chemistry.chemical_compound Wavelength Spectrometry Fluorescence chemistry Coumarins Reagent Stokes shift Intramolecular force Excited state Drug Discovery symbols Indicators and Reagents Derivatization Acetonitrile |
| Zdroj: | CHEMICAL & PHARMACEUTICAL BULLETIN. 53:750-758 |
| ISSN: | 1347-5223 0009-2363 |
| DOI: | 10.1248/cpb.53.750 |
| Popis: | To improve the fluorescence characteristics, especially emission wavelength, of coumarins, various 3-substituted-6-methoxycoumarin derivatives were synthesized, and then benzocoumarin derivatives were also synthesized in expectation of the shift to the longer wavelength region by the extension of the conjugated system. Their fluorescence properties were investigated spectrophotometrically in acetonitrile and evaluated from the viewpoint of the intramolecular charge transfer (ICT) between push- and pull-substituents in the ground and the excited states. Among them, benzocoumarin derivatives especially fluoresced in the longer wavelength around 540 nm with remarkably large Stokes shifts beyond 10000 cm - 1 . Using such fluorophores, some novel fluorescence derivatization reagents for carboxylic acids, alcohols, phenols, and amines were preliminarily prepared as an example, and their derivatized products were also found to fluoresce in the longer wavelength region with large Stokes shifts. |
| Databáze: | OpenAIRE |
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