A Photochemical/Thermal Switch Based on 4,4'-Bis(benzimidazolio)stilbene: Synthesis and Supramolecular Properties.

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Authors

KULKARNI Shantanu Ganesh JELÍNKOVÁ Kristýna NEČAS Marek PRUCKOVÁ Zdeňka ROUCHAL Michal DASTYCHOVÁ Lenka KULHÁNEK Petr VÍCHA Robert

Year of publication 2020
Type Article in Periodical
Magazine / Source ChemPhysChem
MU Faculty or unit

Central European Institute of Technology

Citation
Web https://doi.org/10.1002/cphc.202000472
Doi http://dx.doi.org/10.1002/cphc.202000472
Keywords stilbene switch; cucurbit[n]uril; cyclodextrins; molecular devices; host-guest systems
Description 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 (beta-CD, gamma-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@beta-CD and guest@beta-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.
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