A photochemical/thermal switch based on 4,4′-bis(benzimidazolio)stilbene: Synthesis and supramolecular properties

Abstract

Stilbene derivatives are well-recognised substructures of molecular switches based on photochemically and/or thermally induced (E)/(Z) isomerisation. We combined a stilbene motif with two benzimidazolium arms to prepare new sorts of supramolecular building blocks and examined their binding properties towards cucurbit[n]urils (n=7, 8) and cyclodextrins (β-CD, γ-CD) in water. Based on the 1H NMR data and molecular dynamics simulations, we found that two distinct complexes with different stoichiometry, i. e., guest@β-CD and guest@β-CD2, coexist in equilibrium in a water solution of the (Z)-stilbene-based guests. We also demonstrated that the bis(benzimidazolio)stilbene guests can be transformed from the (E) into the (Z) form via UV irradiation and back via thermal treatment in DMSO. © 2020 Wiley-VCH GmbH