Abstract

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% Förster-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.

Highlights

  • The development of functional nanomaterials is nowadays a very attractive field of fundamental and applied research

  • Monosaccharides can be readily functionalized with several propargyl groups to synthesize, using click chemistry, multivalent neoglycoconjugates for recognition studies with carbohydrate-binding proteins [21,22,23,24] or to develop light-harvesting antenna systems [17]

  • O-Propargylation followed by microwave-assisted CuAAC with azido-functionalized DCM fluorophore 5 [25] in the presence of copper sulfate and sodium ascorbate led to the fluorescent glucoside 6

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Summary

Introduction

The development of functional nanomaterials is nowadays a very attractive field of fundamental and applied research.

Results
Conclusion
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