Photoconversion of o-hydroxycinnamates to coumarins and its application to fluorescence imaging

( E)- o-Hydroxycinnamates were synthesized and their photochemical behavior was investigated in liquid and solid states. It was confirmed by 1H NMR spectroscopy that the ( E)- o-hydroxycinnamates converted into the corresponding coumarins via ( Z)- o-hydroxycinnamate intermediates. The photoconversi...

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Bibliographic Details
Published in:Tetrahedron letters 2009-08, Vol.50 (33), p.4769-4772
Main Authors: Cho, Sung-Youl, Song, Young-Kyu, Kim, Joong-Gon, Oh, Se-Young, Chung, Chan-Moon
Format: Article
Language:English
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Summary:( E)- o-Hydroxycinnamates were synthesized and their photochemical behavior was investigated in liquid and solid states. It was confirmed by 1H NMR spectroscopy that the ( E)- o-hydroxycinnamates converted into the corresponding coumarins via ( Z)- o-hydroxycinnamate intermediates. The photoconversion was greatly accelerated in the presence of p-toluenesulfonic acid. The optical properties of the cinnamates were compared with those of the corresponding coumarins. Fluorescence imaging was successfully accomplished by photoirradiation of PMMA films containing the cinnamates.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.06.031