Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 39, Pages 11559-11563Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201506269
Keywords
carbenes; diarylethenes; nitrogen heterocycles; photochromism; photoswitches
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Funding
- Ministry of Education and the National Research Foundation of Korea
- Office of Naval Research [N00014-14-1-0650]
- National Science Foundation [CHE-0954364, CHE-1361462]
- IBS [IBS-R019-D1]
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The first isolable, photoswitchable N-heterocyclic carbene was synthesized and found to undergo reversible electrocyclic isomerization upon successive exposure to UV and visible radiation. The UV-induced ring closure afforded substantial changes to the electronic structure of the dithienylethene- based NHC, as evidenced by changes in the corresponding UV/Vis absorption and C-13 NMR spectra. Likewise, molecular orbital calculations revealed diminished electron density at the carbene nucleus upon photocyclization, consistent with the enhanced electrophilicity displayed by the ring-closed form. The photoswitchable NHC was successfully switched between its ring-opened and ring-closed states with high fidelity over multiple cycles. Furthermore, the ring-closed isomer was found to undergo facile N-H bond activation, allowing for the controlled capture and release of ammonia upon cycling between its isomeric states.
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