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.
| Original language | English |
|---|---|
| Pages (from-to) | 8559-8564 |
| Number of pages | 6 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 16 |
| Issue number | 44 |
| DOIs | |
| Publication status | Published - 2018 |
Bibliographical note
Funding Information:The authors acknowledge EU funding by the EU H2020-MSCA-RISE-2015 through the PELICO project (grant 690973). DRS acknowledges support from the Engineering and Physical Sciences Research Council (EP/P020291/1) and Royal Society (Wolfson Research Merit Award). K. S. would like to thank Trinity College, Cambridge Trust, Cambridge Nehru Trust and the Cambridge Philosophical Society for providing fellowships. Part of this work was performed using the Darwin Supercomputer of the University of Cambridge High Performance Computing Service (http://www.hpc.cam.ac.uk/), provided by Dell Inc. using Strategic Research Infrastructure Funding from the Higher Education Funding Council for England and funding from the Science and Technology Facilities Council. ASU and SA thank the DFG for supporting GRK 2039, ASU and OB acknowledge the BMBF for VIP-PLUS funding. IVK acknowledges the Alexander von Humboldt Foundation (Germany) for financial support as a recipient of the Georg Forster Research Prize.
Publisher Copyright:
© The Royal Society of Chemistry.