Enabling Racemization of Axially Chiral Subphthalocyanine-Tetracyanobutadiene-Aniline Enantiomers by Triplet State Photogeneration |
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Authors: | Giulia Lavarda Dr. Nicholus Bhattacharjee Dr. Giuseppe Brancato Prof. Tomás Torres Dr. Giovanni Bottari |
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Affiliation: | 1. Departamento de Química Orgánica, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049 Madrid, Spain;2. Scuola Normale Superiore, Piazza dei Cavalieri 7, 56126 Pisa, Italy Istituto Nazionale di Fisica Nucleare, Largo Pontecorvo 3, 56100 Pisa, Italy;3. Scuola Normale Superiore, Piazza dei Cavalieri 7, 56126 Pisa, Italy |
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Abstract: | 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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Keywords: | atropisomer photoracemization subphthalocyanine tetracyano-1,3-butadiene triplet state |
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