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


Type
Article
Change log
Authors
Strizhak, Alexander V 
Sharma, Krishna 
Babii, Oleg 
Afonin, Sergii 
Ulrich, Anne S 
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.

Description
Keywords
0305 Organic Chemistry
Journal Title
Org Biomol Chem
Conference Name
Journal ISSN
1477-0520
1477-0539
Volume Title
16
Publisher
Royal Society of Chemistry (RSC)
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)