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

Andrew T. Turley, Promeet K. Saha, Andrew Danos, Aisha N. Bismillah, Andrew P. Monkman, Dmitry S. Yufit, Basile F. E. Curchod, Marc K. Etherington, Paul R. McGonigal*

*Corresponding author for this work

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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.
Original languageEnglish
Article numbere202202193
Number of pages9
JournalAngewandte Chemie - International Edition
Issue number24
Early online date13 Apr 2022
Publication statusPublished - 13 Jun 2022


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