Highly reactive bis-cyclooctyne-modified diarylethene for SPAAC-mediated cross-linking.
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Peer-reviewed
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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.
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0305 Organic Chemistry
Journal Title
Org Biomol Chem
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Journal ISSN
1477-0520
1477-0539
1477-0539
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16
Publisher
Royal Society of Chemistry (RSC)
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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)
Royal Society (WM150022)
European Commission Horizon 2020 (H2020) Marie Sk?odowska-Curie actions (690973)
Engineering and Physical Sciences Research Council (EP/P020291/1)