α‐Cyano Triaryl[3]radialene: Unsymmetrical Stereo‐configuration, Clustering‐enhanced Excimer Emission, and Radical‐involved Multimodal Information Switching
- 23 May 2023
- journal article
- research article
- Published by Wiley in Angewandte Chemie
- Vol. 62 (27), e202305011
- https://doi.org/10.1002/anie.202305011
Abstract
[3]Radialene has a peculiar topology and cross-conjugation system, representing a unique molecular scaffold in organic materials. Herein, we report a special class of stereoisomeric alpha-cyano triaryl[3]radialenes (CTRs) that show concentration-caused quenching in solution but emit red-shifted and enhanced luminescence in the crystalline state. Clustering of multiple cyano groups and their through-space interactions with the [3]radialene ring significantly extend pi-electron communication meanwhile rigidifying the propeller conformation multivalently, thus playing a key role behind the state-dependent luminescence. These radialenes with a substantial electron affinity undergo a reversible electron transfer transition to anionic radicals with good stability, showing switching of photoabsorption, photoluminescence and electron spin resonance (ESR) signal. We also established proof-of-concept applications of CTRs for multimodal information encryption and chemical sensing.Funding Information
- National Natural Science Foundation of China (51922039, T2122011)
- Basic and Applied Basic Research Foundation of Guangdong Province (2020A1515110786)
- China Postdoctoral Science Foundation (2021M701147)
- Natural Science Foundation of Hunan Province (2022JJ30152, 2021JJ304060)
- Scientific Research Foundation of Hunan Provincial Education Department (20C1149)
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