期刊
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
卷 -, 期 12, 页码 2453-2457出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/b006449l
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Coumarins exhibit fluorescence that is dependent on the nature of their substituents. We have found that the strong fluorescence of 7-hydroxycoumarin in aqueous media is completely lost in 7-aryloxycoumarins. Judging from the relation between the electron-donating character of the substituent at the 7-position and the relative quantum efficiency of fluorescence, we considered that the fluorescence properties of 7-hydroxycoumarin derivatives can be explained in terms of the intramolecular charge transfer (ICT) mechanism. On this basis, we designed and synthesized 7-(4'-hydroxyphenoxy)coumarin, 7-(2'-hydroxyphenoxy)coumarin, 7-(4'-aminophenoxy)coumarin and 7-(2'-aminophenoxy)coumarin, which we expected would be dearylated by highly reactive oxygen species. We found that these nonfluorescent aryloxycoumarins were dearylated to afford highly fluorescent 7-hydroxycoumarin upon reaction specifically with hydroxyl radical ((OH)-O-.), but not superoxide (O-2(-)), hydrogen peroxide (H2O2), or singlet oxygen (O-1(2)). We suggest that these compounds may be applicable as specific fluorescence probes for hydroxyl radicals in an aqueous environment.
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