The stability of a photocatalyst under irradiation is important in photoredox applications. In this work, we investigated the stability of a thermally activated delayed fluorescence (TADF) photocatalyst {3DPAFIPN [2,4,6-tris(diphenylamino)-5-fluoroisophthalonitrile]}, recently employed in photoredox-mediated processes, discovering that in the absence of quenchers the chromophore is unstable and is efficiently converted by irradiation with visible light into another species based on the carbazole-1,3-dicarbonitrile moiety. The new species obtained is itself a TADF emitter and finds useful applications in photoredox transformations. At the excited state, it is a strong reductant and was efficiently applied to cobalt-mediated allylation of aldehydes, whereas other TADFs (4CzIPN and 3DPAFIPN) failed to promote efficient photocatalytic cycles.

Pinosa, E., Bassan, E., Cetin, S., Villa, M., Potenti, S., Calogero, F., et al. (2023). Light-Induced Access to Carbazole-1,3-dicarbonitrile: A Thermally Activated Delayed Fluorescent (TADF) Photocatalyst for Cobalt-Mediated Allylations. JOURNAL OF ORGANIC CHEMISTRY, 88(10), 6390-6400 [10.1021/acs.joc.2c01825].

Light-Induced Access to Carbazole-1,3-dicarbonitrile: A Thermally Activated Delayed Fluorescent (TADF) Photocatalyst for Cobalt-Mediated Allylations

Pinosa, Emanuele
Primo
;
Bassan, Elena;Cetin, Sultan;Villa, Marco;Potenti, Simone;Calogero, Francesco;Gualandi, Andrea
;
Fermi, Andrea
;
Ceroni, Paola;Cozzi, Pier Giorgio
2023

Abstract

The stability of a photocatalyst under irradiation is important in photoredox applications. In this work, we investigated the stability of a thermally activated delayed fluorescence (TADF) photocatalyst {3DPAFIPN [2,4,6-tris(diphenylamino)-5-fluoroisophthalonitrile]}, recently employed in photoredox-mediated processes, discovering that in the absence of quenchers the chromophore is unstable and is efficiently converted by irradiation with visible light into another species based on the carbazole-1,3-dicarbonitrile moiety. The new species obtained is itself a TADF emitter and finds useful applications in photoredox transformations. At the excited state, it is a strong reductant and was efficiently applied to cobalt-mediated allylation of aldehydes, whereas other TADFs (4CzIPN and 3DPAFIPN) failed to promote efficient photocatalytic cycles.
2023
Pinosa, E., Bassan, E., Cetin, S., Villa, M., Potenti, S., Calogero, F., et al. (2023). Light-Induced Access to Carbazole-1,3-dicarbonitrile: A Thermally Activated Delayed Fluorescent (TADF) Photocatalyst for Cobalt-Mediated Allylations. JOURNAL OF ORGANIC CHEMISTRY, 88(10), 6390-6400 [10.1021/acs.joc.2c01825].
Pinosa, Emanuele; Bassan, Elena; Cetin, Sultan; Villa, Marco; Potenti, Simone; Calogero, Francesco; Gualandi, Andrea; Fermi, Andrea; Ceroni, Paola; Cozzi, Pier Giorgio
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/905024
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