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Photoconversion of o-hydroxycinnamates to coumarins and its application to fluorescence imaging
Authors:Sung-Youl Cho  Joong-Gon Kim  Chan-Moon Chung
Affiliation:a Department of Chemistry, Yonsei University, Wonju, Kangwon-do 220-710, South Korea
b Biotechnology Division, Hanwha Chemical R&D Center, Taejon 305-345, South Korea
c Department of Chemical and Biomolecular Engineering, Sogang University, Seoul 121-742, South Korea
Abstract:(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.
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