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Paper | Regular issue | Vol 106, No. 2, 2023, pp.277-289
Published online, 7th December, 2022
DOI: 10.3987/COM-22-14771
■ Supramolecular Self-Assembly Based on Symmetric Tetramethyl-Substituted Cucurbit[6]uril and Small Aromatic Amines

Lin Zhang, Jun Zheng, Xuanxun Wang, Zhu Tao, and Qianjun Zhang*

*Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Institute of Applied Chemistry, Guizhou University, Guiyang, 550025, China

Abstract

In this paper, the interactions formed between symmetric tetramethyl-substituted cucurbit[6]uril (TMeQ[6]) and 4-cyanoaniline (CYA), 4,4'-methylenedianiline (MET), and 4-benzylaniline (BEN), were investigated using 1H NMR spectroscopy and X-ray single crystal diffraction analysis. X-Ray single crystal diffraction showed that CYA was encapsulated in the cavity of TMeQ[6] and formed 1:1 host-guest complex 1. Both MET and BEN were located at the TMeQ[6] portal and coordinated to form complex 2 and complex 3, respectively, forming weak interactions with TMeQ[6], such as hydrogen bonding, C-H···π interactions, and ion-dipole interactions. Complexes 1~3 self-assemble to construct supramolecular nanoscale structures under the induction of [ZnCl4]2- ions. The 1H NMR spectroscopic analysis supported the crystallographic results in which an clathration or portal interaction occured between host and guest molecules.