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

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.

Automated summary

This study investigates the photophysical and electrochemical properties of a new class of fluorinated benzonitrile compounds that are substituted with mixed phenoxazine and carbazole units. The compounds exhibit dual broad emission due to both localized and charge-transfer absorptions over a large range of the UV-vis spectrum. In solution, their photoluminescence quantum yields vary from a few percent to 18% in a more rigid environment. Additionally, the compounds demonstrate thermally activated delayed fluorescence, which is influenced by the number of phenoxazine substituents. Electrochemistry also reveals significant changes in the reduction mechanisms based on the remaining fluorine atoms on the benzonitrile core.