Synthesis and fluorescence study of 6,7-diaminocoumarin and its imidazolo derivatives

Novel 6,7-diamino-4-methylcoumarin and derived imidazolocoumarins were synthesized and their absorption and fluorescence properties were recorded in solvents of varying polarity. 6,7-Diamino-4-methylcoumarin is highly fluorescent, with a quantum yield of 0.78 in dioxane. The fluorescence intensity o...

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Bibliographic Details
Published in:Dyes and pigments 2013-02, Vol.96 (2), p.525-534
Main Authors: Sheshashena Reddy, T., Ram Reddy, A.
Format: Article
Language:English
Subjects:
6,7-Diamino-4-methylcoumarin
Carbonyl compounds
Cinnamaldehyde
Derivatives
Dyes
Fluorescence
Polarity
Quantum yield and Derivatization
Quenching
Solvatochromism
Solvents
Synthesis
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Summary:Novel 6,7-diamino-4-methylcoumarin and derived imidazolocoumarins were synthesized and their absorption and fluorescence properties were recorded in solvents of varying polarity. 6,7-Diamino-4-methylcoumarin is highly fluorescent, with a quantum yield of 0.78 in dioxane. The fluorescence intensity of 6,7-diamino-4-methylcoumarin, when mixed with different carbonyl group containing compounds, decreased. Based on the interaction of this diaminocoumarin with the carbonyl compound a fluorescent sensor with high selectivity towards electron rich benzaldehydes and cinnamaldehyde was developed. Green emissive diaminocoumarin on addition of benzaldehydes with electron donating groups turns to blue emissive arylimidazolocoumarin. [Display omitted] ► Synthesis of novel coumarin dyes. ► Solvent and structure dependent fluorescence. ► Selective detection of electron donating benzaldehydes and cinnamaldehyde by 6,7-diamino-4-methylcoumarin.
ISSN:0143-7208
1873-3743
DOI:10.1016/j.dyepig.2012.08.021