Publication: The synthesis and fluorescence properties of novel chromenone-crown ethers
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Date
2010
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TAYLOR & FRANCIS LTD
Abstract
o-Dihyroxy-3-phenylchromenone derivatives, namely, 6,7-dihydroxy-3-(3',4'-dimethoxyphenyl)chromenone and 6,7-dimethoxy-3-(3',4'-dihydroxyphenyl)chromenone, were obtained from 2,4,5-trihydroxybenzaldehyde/3,4-dimethoxyphenylacetic acid and 2-hydroxy-4,5-dimethoxybenzaldehyde/3,4-dihydroxyphenylacetic acid, respectively, in the presence of acetic anhydride and sodium acetate under an inert atmosphere, after treatment with MeOH/HCl(aq). The chromenone-crown ethers were prepared from cyclic condensation of o-dihydroxy-3-phenylchromenones with poly(ethylene glycol) ditosylates in the presence of CH3CN/alkali metal carbonates. The chromatographically purified novel chromenone-crown ethers were identified by 1H NMR, MALDI-TOF mass spectrometry and elemental analysis. The fluorescence and UV-vis spectroscopic properties of the obtained chromenone-crown ethers and their complexes with Li+, Na+ and K+ perchlorate salts were estimated in acetonitrile. The quantum yields of novel chromenone-crown ethers were determined by the comparative method. [image omitted].
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Keywords
chromenone-crown ethers, 3-phenylchromenone, quantum yield, synthesis, cation binding, CATION-BINDING, COMPLEXATION, CONDUCTOMETRY, MACROCYCLES, RECOGNITION, DERIVATIVES, EXTRACTION, SPECTRA