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

Turley, Andrew Thomas, Saha, Promeet Kar, Danos, Andrew, Bismillah, Aisha Naziran, Monkman, Andrew P, Yufit, Dmitry S, Curchod, Basile F E, Etherington, Marc and McGonigal, Paul Ronald (2022) Extended Conjugation Attenuates the Quenching of Aggregation‐Induced Emitters by Photocyclization Pathways. Angewandte Chemie International Edition, 61 (24). e202202193. ISSN 1433-7851

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Official URL: https://doi.org/10.1002/anie.202202193

Abstract

Herein, we expose how the antagonistic relationship between solid-state luminescence and photocyclization of oligoaryl alkene 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.

Item Type: Article
Additional Information: Funding information: A.T.T., P.K.S. and A.N.B. gratefully acknowledge the Engineering and Physical Sciences Research Council (EPSRC) for Doctoral Training Grants (EP/N509462/1, EP/R513039/1, and EP/M507854/1, respectively). B.F.E.C. thanks the facilities of the Hamilton HPC Service of Durham University. P.R.M. acknowledges funding from the Northeast Centre for Energy Materials (NECEM). We thank Prof Ian Baxendale for useful discussions and access to a photoreactor.
Uncontrolled Keywords: Carbocycles, Fluorescence, Aggregation-Induced Emission, Molecular Rotors, Photochemistry
Subjects: F100 Chemistry
F200 Materials Science
F300 Physics
Department: Faculties > Engineering and Environment > Mathematics, Physics and Electrical Engineering
Depositing User: Rachel Branson
Date Deposited: 05 Apr 2022 14:10
Last Modified: 24 Jun 2022 15:15
URI: http://nrl.northumbria.ac.uk/id/eprint/48820

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