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

KULKARNI, Shantanu Ganesh, Kristýna JELÍNKOVÁ, Marek NEČAS, Zdeňka PRUCKOVÁ, Michal ROUCHAL, Lenka DASTYCHOVÁ, Petr KULHÁNEK and Robert VÍCHA. A Photochemical/Thermal Switch Based on 4,4'-Bis(benzimidazolio)stilbene: Synthesis and Supramolecular Properties. ChemPhysChem. Weinheim: Wiley, 2020, vol. 21, No 18, p. 2084-2095. ISSN 1439-4235. Available from: https://dx.doi.org/10.1002/cphc.202000472.

Basic information

• Original name: A Photochemical/Thermal Switch Based on 4,4'-Bis(benzimidazolio)stilbene: Synthesis and Supramolecular Properties.
• Authors: KULKARNI, Shantanu Ganesh, Kristýna JELÍNKOVÁ, Marek NEČAS (203 Czech Republic, belonging to the institution), Zdeňka PRUCKOVÁ, Michal ROUCHAL, Lenka DASTYCHOVÁ, Petr KULHÁNEK (203 Czech Republic, guarantor, belonging to the institution) and Robert VÍCHA.
• Edition: ChemPhysChem, Weinheim, Wiley, 2020, 1439-4235.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10400 1.4 Chemical sciences
• Country of publisher: Germany
• Confidentiality degree: is not subject to a state or trade secret
• WWW: URL
• Impact factor: Impact factor: 3.102
• RIV identification code: RIV/00216224:14740/20:00118083
• Organization unit: Central European Institute of Technology
• Doi: http://dx.doi.org/10.1002/cphc.202000472
• UT WoS: 000563816800001
• Keywords in English: stilbene switch; cucurbit[n]uril; cyclodextrins; molecular devices; host-guest systems
• Tags: CF CRYO, CF SAXS, rivok
• Tags: International impact, Reviewed

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 (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.

Links

• LM2015085, research and development project: Name: CERIT Scientific Cloud (Acronym: CERIT-SC)

Investor: Ministry of Education, Youth and Sports of the CR, CERIT Scientific Cloud

• LM2018127, research and development project: Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)

Investor: Ministry of Education, Youth and Sports of the CR

• LQ1601, research and development project: Name: CEITEC 2020 (Acronym: CEITEC2020)

Investor: Ministry of Education, Youth and Sports of the CR

• 90042, large research infrastructures: Name: CESNET II
• 90070, large research infrastructures: Name: IT4Innovations