Bicyclo[2.2.0]hexene derivatives as a proaromatic platform for group transfer and chemical sensing

Bin Wu, Jianing Wang, Xingchen Liu and Rong Zhu ()
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Bin Wu: Peking University
Jianing Wang: Peking University
Xingchen Liu: Peking University
Rong Zhu: Peking University

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: Abstract Here we report the design, preparation, synthetic utility, and sensing application of a class of proaromatic structures, namely bicyclo[2.2.0]hexene (BCH) derivatives. Building on a valence isomerism concept, they feature modular and easy synthesis as well as high thermal stability, and can be oxidatively activated under mild conditions. New alkyl transfer reactions using BCHs as a radical donor have been developed to showcase the utility of their proaromaticity. Moreover, the redox-triggered valence isomerization of a quinoline-derived BCH led to colorimetric and fluorescent responses toward vapors of electrophilic reagents in solution and solid phase, respectively. This optical response was shown to involve a 1,3-cyclohexadiene structure that possesses an intramolecular charge transfer excited state with interesting aggregation induced emission (AIE) character. Thus, the potential of BCHs has been demonstrated as a versatile platform for the development of new reagents and functional materials.

Date: 2021
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DOI: 10.1038/s41467-021-24054-3

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