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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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 |
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| 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: | 13 Apr 2023 08:00 |
| URI: | https://nrl.northumbria.ac.uk/id/eprint/48820 |
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