Extended Conjugation Attenuates the Quenching of Aggregation-Induced Emitters by Photocyclization Pathways

Turley, A.T.; Saha, P.K.; Danos, A.; Bismillah, A.N.; Monkman, A.P.; Yufit, D.S.; Curchod, B.F.E.; Etherington., M.K.; McGonigal, P.R.

doi:10.1002/anie.202202193

Extended Conjugation Attenuates the Quenching of Aggregation-Induced Emitters by Photocyclization Pathways

Turley, A.T.; Saha, P.K.; Danos, A.; Bismillah, A.N.; Monkman, A.P.; Yufit, D.S.; Curchod, B.F.E.; Etherington., M.K.; McGonigal, P.R.

Authors

A.T. Turley

P.K. Saha

Dr Andrew Danos andrew.danos@durham.ac.uk
Senior Experimental Officer

Dr Aisha Bismillah aisha.n.bismillah@durham.ac.uk
Academic Visitor

Professor Andrew Monkman a.p.monkman@durham.ac.uk
Professor

Dr Dmitry Yufit d.s.yufit@durham.ac.uk
Academic Visitor

Dr Basile Curchod basile.f.curchod@durham.ac.uk
Academic Visitor

M.K. Etherington.

Dr Paul Mcgonigal paul.mcgonigal@durham.ac.uk
Academic Visitor

Abstract

Herein, we expose how the antagonistic relationship between solid-state luminescence and photocyclization of oligoaryl alkenes chromophores is modulated by the conjugation length of their alkenyl backbones. Heptaaryl cycloheptatriene molecular rotors exhibit aggregation-induced emission characteristics. We show that their emission is turned off upon breaking the conjugation of the cycloheptatriene by epoxide formation. While this modification is deleterious to photoluminescence, it enables formation of extended polycyclic frameworks by Mallory reactions. We exploit this dichotomy (i) to manipulate emission properties in a controlled manner and (ii) as a synthetic tool to link together pairs of phenyl rings in a specific sequence. This method to alter the tendency of oligoaryl alkenes to undergo photocyclization can inform the design of solid-state emitters that avoid this quenching mechanism, while also allowing selective cyclization in syntheses of polycyclic aromatic hydrocarbons.

Citation

Turley, A., Saha, P., Danos, A., Bismillah, A., Monkman, A., Yufit, D., …McGonigal, P. (2022). Extended Conjugation Attenuates the Quenching of Aggregation-Induced Emitters by Photocyclization Pathways. Angewandte Chemie International Edition, 61(24), Article e202202193. https://doi.org/10.1002/anie.202202193

Journal Article Type	Article
Acceptance Date	Mar 27, 2022
Online Publication Date	Mar 28, 2022
Publication Date	Jun 13, 2022
Deposit Date	Mar 28, 2022
Publicly Available Date	Mar 29, 2022
Journal	Angewandte Chemie International Edition
Print ISSN	1433-7851
Electronic ISSN	1521-3773
Publisher	Wiley
Peer Reviewed	Peer Reviewed
Volume	61
Issue	24
Article Number	e202202193
DOI	https://doi.org/10.1002/anie.202202193

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