An Isolable, Photoswitchable N-Heterocyclic Carbene: On-Demand Reversible Ammonia Activation
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- An Isolable, Photoswitchable N-Heterocyclic Carbene: On-Demand Reversible Ammonia Activation
- Aaron J. Teator; Yuan Tian; Mu Chen; Jeehiun K. Lee; Christopher W. Bielawski
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.54, no.39, pp.11559 - 11563
- WILEY-V C H VERLAG GMBH
- 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 13C 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. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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