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A Photochemical/Thermal Switch Based on 4,4′‐Bis(benzimidazolio)stilbene: Synthesis and Supramolecular Properties.
Author(s) -
Kulkarni Shantanu Ganesh,
Jelínková Kristýna,
Nečas Marek,
Prucková Zdeňka,
Rouchal Michal,
Dastychová Lenka,
Kulhánek Petr,
Vícha Robert
Publication year - 2020
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.202000472
Subject(s) - supramolecular chemistry , isomerization , stoichiometry , chemistry , irradiation , molecular dynamics , photochemistry , proton nmr , photochromism , molecule , stereochemistry , computational chemistry , organic chemistry , catalysis , physics , nuclear physics
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 1 H NMR data and molecular dynamics simulations, we found that two distinct complexes with different stoichiometry, i. e., guest@β‐CD and guest@β‐CD 2 , 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.