ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Supramolecular self-assembly between symmetric tetramethyl cucurbit[6]uril and 1,2-Di(4-pyridyl)ethylene derivative

Cai-Lai Yue, Hai-Yan Wang, Mao-Xia Yang, Yang Luo, Qian-Jun Zhang, Zhu Tao, and Xin Xiao

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

E-mail: ouyyangl@126.com

Received: 28 April 2023  Accepted: 10 September 2023

Abstract:

In recent years, symmetrical α,α′,δ,δ′-tetramethyl-cucurbit[6]uril (TMeQ[6]) has attracted much attention from many researchers due to its interesting assembly pattern. Herein, we have investigated the host–guest interactions pattern of the symmetric TMeQ[6] with (E)-1-(5-carboxypentyl)-4-(2-(pyridin-4-yl)vinyl)pyridin-1-ium. (ECPP). Furthermore, their binding behaviors were investigated by ¹H NMR spectroscopy, MALDI-TOF mass spectrometry, isothermal titration calorimeter, fluorescence, and UV–vis spectrum. The results indicate that TMeQ[6] and ECPP form host–guest complexes in a host/guest molar ratio of 1:1. TMeQ[6] is bound with the vinylpyridine group of ECPP. In addition, TMeQ[6]-ECPP exhibits a high association constant Ka = (1.520 ± 0.58) × 10⁶ M⁻¹, ΔH =  − 53.40 kJ/mol, ΔS =  − 60 J/mol·K. which provides a promising foundation for potential studies of the assemblies.

Graphical abstract

Keywords: Host–guest complexes; TMeQ[6]; Vinylpyridine derivative; Spectroscopy

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-03074-x

Chemical Papers 77 (12) 7625–7631 (2023)