Separation of benzene and toluene associated with vapochromic behaviors by hybrid[4]arene-based co-crystals

Jingyu Chen, Wenjie Zhang, Wenzhi Yang, Fengcheng Xi, Hongyi He, Minghao Liang, Qian Dong, Jiawang Hou, Mengbin Wang (), Guocan Yu () and Jiong Zhou ()
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Jingyu Chen: Northeastern University
Wenjie Zhang: Northeastern University
Wenzhi Yang: Northeastern University
Fengcheng Xi: Northeastern University
Hongyi He: Northeastern University
Minghao Liang: Northeastern University
Qian Dong: Northeastern University
Jiawang Hou: Northeastern University
Mengbin Wang: Zhejiang University
Guocan Yu: Tsinghua University
Jiong Zhou: Northeastern University

Nature Communications, 2024, vol. 15, issue 1, 1-13

Abstract: Abstract The combination of macrocyclic chemistry with co-crystal engineering has promoted the development of materials with vapochromic behaviors in supramolecular science. Herein, we develop a macrocycle co-crystal based on hybrid[4]arene and 1,2,4,5-tetracyanobenzene that is able to construct vapochromic materials. After the capture of benzene and toluene vapors, activated hybrid[4]arene-based co-crystal forms new structures, accompanied by color changes from brown to yellow. However, when hybrid[4]arene-based co-crystal captures cyclohexane and pyridine, neither structures nor colors change. Interestingly, hybrid[4]arene-based co-crystal can separate benzene from a benzene/cyclohexane equal-volume mixture and allow toluene to be removed from a toluene/ pyridine equal-volume mixture with purities reaching 100%. In addition, the process of adsorptive separation can be visually monitored. The selectivity of benzene from a benzene/cyclohexane equal-volume mixture and toluene from a toluene/ pyridine equal-volume mixture is attributed to the different changes in the charge-transfer interaction between hybrid[4]arene and 1,2,4,5-tetracyanobenzene when hybrid[4]arene-based co-crystal captures different vapors. Moreover, hybrid[4]arene-based co-crystal can be reused without losing selectivity and performance. This work constructs a vapochromic material for hydrocarbon separation.

Date: 2024
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DOI: 10.1038/s41467-024-45592-6

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