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Novel Easy to Synthesize Benzonitrile Compounds with Mixed Carbazole and Phenoxazine Substituents Exhibiting Dual Emission and TADF Properties

Maggiore, Antonio; Qu, Yangyang; Guillot, Régis; Pander, Piotr; Vasylieva, Marharyta; Data, Przemyslaw; Dias, Fernando B.; Audebert, Pierre; Clavier, Gilles; Miomandre, Fabien

Novel Easy to Synthesize Benzonitrile Compounds with Mixed Carbazole and Phenoxazine Substituents Exhibiting Dual Emission and TADF Properties Thumbnail


Authors

Antonio Maggiore

Yangyang Qu

Régis Guillot

Marharyta Vasylieva

Przemyslaw Data

Pierre Audebert

Gilles Clavier

Fabien Miomandre



Abstract

The photophysical and electrochemical properties of a new class of fluorinated benzonitrile compounds substituted with mixed phenoxazine and carbazole units have been investigated. When absorbing in a large range of the UV–vis spectrum due to both localized and charge-transfer absorptions, these compounds show dual broad emission in solution and intense emission in PMMA films, with photoluminescence quantum yields changing from a few percent in solution to 18% in a more rigid environment. The compounds also exhibit thermally activated delayed fluorescence demonstrated by the role of oxygen in the quenching of delayed fluorescence and by time-resolved luminescence studies, with an efficiency directly related to the number of phenoxazine substituents. Electrochemistry reveals dramatic changes in the reduction mechanisms according to the number of remaining fluorine atoms on the benzonitrile core. All these results demonstrate how it is possible to tune the photophysical and electrochemical properties of easily synthesizable derivatives by controlling the nature and relative number of the substituents on a simple aromatic platform.

Citation

Maggiore, A., Qu, Y., Guillot, R., Pander, P., Vasylieva, M., Data, P., …Miomandre, F. (2022). Novel Easy to Synthesize Benzonitrile Compounds with Mixed Carbazole and Phenoxazine Substituents Exhibiting Dual Emission and TADF Properties. Journal of Physical Chemistry B (Soft Condensed Matter and Biophysical Chemistry), 126(14), 2740-2753. https://doi.org/10.1021/acs.jpcb.2c00219

Journal Article Type Article
Online Publication Date Mar 30, 2022
Publication Date Apr 14, 2022
Deposit Date Jun 17, 2022
Publicly Available Date Mar 30, 2023
Journal Journal of Physical Chemistry B (Soft Condensed Matter and Biophysical Chemistry)
Print ISSN 1520-6106
Electronic ISSN 1520-5207
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 126
Issue 14
Pages 2740-2753
DOI https://doi.org/10.1021/acs.jpcb.2c00219

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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Physical Chemistry B, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.jpcb.2c00219





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