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