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

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Authors
Strizhak, Alexander V
Sharma, Krishna
Babii, Oleg
Afonin, Sergii
Ulrich, Anne S
Komarov, Igor V
Spring, David R
Publication Date
2018-11-14
Journal Title
Org Biomol Chem
ISSN
1477-0520
Publisher
Royal Society of Chemistry (RSC)
Volume
16
Issue
44
Pages
8559-8564
Language
eng
Type
Article
Physical Medium
Print
Metadata
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Citation
Strizhak, A. V., Sharma, K., Babii, O., Afonin, S., Ulrich, A. S., Komarov, I. V., & Spring, D. R. (2018). Highly reactive bis-cyclooctyne-modified diarylethene for SPAAC-mediated cross-linking.. Org Biomol Chem, 16 (44), 8559-8564. https://doi.org/10.1039/c8ob02428f
Abstract
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.
Keywords
0305 Organic Chemistry
Sponsorship
European Research Council (279337)
Royal Society (WM150022)
European Commission Horizon 2020 (H2020) Marie Sk?odowska-Curie actions (690973)
Engineering and Physical Sciences Research Council (EP/P020291/1)
Identifiers
External DOI: https://doi.org/10.1039/c8ob02428f
This record's URL: https://www.repository.cam.ac.uk/handle/1810/286309
Rights
Attribution 4.0 International
Licence URL: https://creativecommons.org/licenses/by/4.0/
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Attribution 4.0 International
Except where otherwise noted, this item's licence is described as Attribution 4.0 International