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Highly reactive bis-cyclooctyne-modified diarylethene for SPAAC-mediated cross-linking

Org. Biomol. Chem. 2018, 16 (44), 8559-8564

DOI: 10.1039/C8OB02428F

Strizhak A.; Sharma K.; Babii O.; Afonin S.; Ulrich A.; Komarov I.; Spring D.

Photoisomerizable diarylethenes equipped with triple bonds are promising building blocks for constructing bistable photocontrollable systems. Here we report on the design, synthesis and application of a cross-linking reagent which is based on a diarylethene core and features two strained cyclooctynes. High reactivity of the cyclooctyne rings in catalyst-free 1,3-dipolar cycloaddition reactions was suggested to stem from the additional strain imposed by the fused thiophene rings. This hypothesis was confirmed by quantum chemical calculations.

Highly reactive bis-cyclooctyne-modified diarylethene

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