Turley, Andrew T., Saha, Promeet K., Danos, Andrew et al. (6 more authors) (2022) Extended Conjugation Attenuates the Quenching of Aggregation-Induced Emitters by Photocyclization Pathways. Angewandte Chemie - International Edition. e202202193. ISSN 1433-7851
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.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2022 The Authors. 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. |
Keywords: | Aggregation-Induced Emission,Carbocycles,Fluorescence,Molecular Rotors,Photochemistry |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 02 Mar 2023 15:50 |
Last Modified: | 17 Dec 2024 00:25 |
Published Version: | https://doi.org/10.1002/anie.202202193 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1002/anie.202202193 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:196977 |
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Description: Angew Chem Int Ed - 2022 - Turley - Extended Conjugation Attenuates the Quenching of Aggregation‐Induced Emitters by
Licence: CC-BY 2.5