Construction of supramolecular self-assembly of cyclobutanocucurbit[5]uril and six aromatic amines

Abstract

Supramolecular self-assemblies are molecular aggregates formed by the combination of multiple molecules via intermolecular noncovalent bonding interactions. The synergy of hydrogen bonds and weak intermolecular interactions endows them with specific structures and functionalities. In this paper, 1H NMR spectroscopy, HPLC-QTOF mass spectrometry and other characterization methods were used to investigate the interaction modes of cyclobutanocucurbit[5]uril (CyB5Q[5]) and six aromatic amine compounds. The results showed that the negative electrostatic portal carbonyls of CyB5Q[5] interacted with the guest molecules via hydrogen bonding. The benzene ring in the guest molecules interacted with the methylene groups on the outer surface of CyB5Q[5] via CH···π interactions. [ZnCl4]2– anions acted as a structure-directing agent and participated in the ion-dipole interactions with the positive electrostatic outer surface of CyB5Q[5]. Three weak intermolecular interactions synergistically constructed a series of multi-level supramolecular self-assembly materials.