Highly reactive bis-cyclooctyne-modified diarylethene for SPAAC-mediated cross-linking.
Strizhak, Alexander V
Organic & biomolecular chemistry
Royal Society of Chemistry (RSC)
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Strizhak, A. V., Sharma, K., Babii, O., Afonin, S., Ulrich, A. S., Komarov, I. V., & Spring, D. (2018). Highly reactive bis-cyclooctyne-modified diarylethene for SPAAC-mediated cross-linking.. Organic & biomolecular chemistry, 16 (44), 8559-8564. https://doi.org/10.1039/c8ob02428f
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.
European Research Council (279337)
Royal Society (WM150022)
European Commission Horizon 2020 (H2020) Marie Sk?odowska-Curie actions (690973)
External DOI: https://doi.org/10.1039/c8ob02428f
This record's URL: https://www.repository.cam.ac.uk/handle/1810/286309
Attribution 4.0 International
Licence URL: https://creativecommons.org/licenses/by/4.0/