Fluorescent sensors, whose fluorescence properties can be changed by binding to or reacting with each analyte molecular species, enable the estimation of its concentration or activity. Structures of most small molecule-based fluorescent sensors consist of fluorophore and the recognition site for each analyte, and both of them are covalently linked at each appropriate position. We developed various fluorescent sensors based on coumarin as fluorophore by introducing recognition sites via two orthogonal reactions, Suziki-Miyaura coupling reaction and Husigen 1,3-cycloaddition reaction. Thus, bromo- and/or azido-substituted coumarin moieties were conjugated with various arylboronic acids or phenylacetylenes, yielding several fluorescent sensors with various mode of fluorescent change. In addition, multi-analyte type fluorescent sensor, in which the modes of fluorescent changes induced by two analytes were different from each other, could be also obtained.

Development of various fluorescent sensors based on coumarin utilizing two orthogonal reactions

244th National Meeting (2012)

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