Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 47, Pages 21224-21229Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202010133
Keywords
atropisomer; photoracemization; subphthalocyanine; tetracyano-1; 3-butadiene; triplet state
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Funding
- Spanish MICINN [CTQ2017-85393-P]
- Scuola Normale Superiore research program
- Severo Ochoa Programme for Centres of Excellence in RD (MINECO) [SEV2016-0686]
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In recent years, several tetracyanobuta-1,3-diene (TCBD) conjugates have been prepared by linking the tetracyano unit to various electroactive moieties. These push-pull conjugates, besides showing interesting physicochemical properties, are axially chiral, a feature arising from the restricted rotation around the central bond of the butadiene. Yet, only in a few cases, separation and isolation of the enantiomers have been successfully achieved, owing to the configurational lability of the corresponding enantiopure species. Herein, we report the first example of photo- and electroactive TCBD-based derivatives showing unprecedented configurational stability and a peculiar light-triggered enantiomer conversion mechanism enabled by triple-state photogeneration. These systems represent a nice addition to the fast-increasing arsenal of artificial, light-controllable molecular switches.
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