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Multichromophoric sugar for fluorescence photoswitching

Maisonneuve, S; Metivier, R; Yu, P; Nakatani, K; Xie, J BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10, 1471-1481.

A multichromophoric glucopyranoside 2 bearing three dicyanomethylenepyran (DCM) fluorophores and one diarylethene (DAE) photochrome has been prepared by Cu(I)-catalyzed alkyne-azide cycloaddition reaction. The fluorescence of 2 was switched off upon UV irradiation, in proportion with the open to closed form (OF to CF) conversion extent of the DAE moiety. A nearly 100% Forster-type resonance energy transfer (FRET) from all three DCM moieties to a single DAE (in its CF) moiety was achieved. Upon visible irradiation, the initial fluorescence intensity was recovered. The observed photoswiching is reversible, with excellent photo resistance.

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Publication

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Paru le 30 juin 2014

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DOI: 10.3762/bjoc.10.151