Grinding-induced supramolecular charge-transfer assemblies with switchable vapochromism toward haloalkane isomers

Jia-Rui Wu, Gengxin Wu, Dongxia Li, Meng-Hao Li, Yan Wang and Ying-Wei Yang ()
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Jia-Rui Wu: Jilin University
Gengxin Wu: Jilin University
Dongxia Li: Jilin University
Meng-Hao Li: Jilin University
Yan Wang: Jilin University
Ying-Wei Yang: Jilin University

Nature Communications, 2023, vol. 14, issue 1, 1-12

Abstract: Abstract Synthetic macrocycles have proved to be of great application value in functional charge-transfer systems in the solid state in recent years. Here we show a switchable on-off type vapochromic system toward 1-/2-bromoalkane isomers by constructing solid-state charge-transfer complexes between electron-rich perethylated pillar[5]arene and electron-deficient aromatic acceptors including 4-nitrobenzonitrile and 1,4-dinitrobenzene. These charge-transfer complexes with different colors show opposite color changes upon exposure to the vapors of 1-bromoalkanes (fading) and 2-bromoalkanes (deepening). Single-crystal structures incorporating X-ray powder diffraction and spectral analyses demonstrate that this on-off type vapochromic behavior is mainly attributed to the destruction (off) and reconstruction (on) of the charge-transfer interactions between perethylated pillar[5]arene and the acceptors, for which the competitive host-guest binding of 1-bromoalkanes and the solid-state structural transformation triggered by 2-bromoalkanes are respectively responsible. This work provides a simple colorimetric method for distinguishing positional isomers with similar physical and chemical properties.

Date: 2023
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DOI: 10.1038/s41467-023-41713-9

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