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

J 2020

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 et. al.

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

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10400 1.4 Chemical sciences

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

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

Abstract

V originále

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

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

90127, large research infrastructures

Name: CIISB II

Citovat

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.

@article{1736716,
   author = {Kulkarni, Shantanu Ganesh and Jelínková, Kristýna and Nečas, Marek and Prucková, Zdeňka and Rouchal, Michal and Dastychová, Lenka and Kulhánek, Petr and Vícha, Robert},
   article_location = {Weinheim},
   article_number = {18},
   doi = {http://dx.doi.org/10.1002/cphc.202000472},
   keywords = {stilbene switch; cucurbit[n]uril; cyclodextrins; molecular devices; host-guest systems},
   language = {eng},
   issn = {1439-4235},
   journal = {ChemPhysChem},
   title = {A Photochemical/Thermal Switch Based on 4,4'-Bis(benzimidazolio)stilbene: Synthesis and Supramolecular Properties.},
   url = {https://doi.org/10.1002/cphc.202000472},
   volume = {21},
   year = {2020}
}

TY  - JOUR
ID  - 1736716
AU  - Kulkarni, Shantanu Ganesh - Jelínková, Kristýna - Nečas, Marek - Prucková, Zdeňka - Rouchal, Michal - Dastychová, Lenka - Kulhánek, Petr - Vícha, Robert
PY  - 2020
TI  - A Photochemical/Thermal Switch Based on 4,4'-Bis(benzimidazolio)stilbene: Synthesis and Supramolecular Properties.
JF  - ChemPhysChem
VL  - 21
IS  - 18
SP  - 2084-2095
EP  - 2084-2095
PB  - Wiley
SN  - 14394235
KW  - stilbene switch
KW  - cucurbit[n]uril
KW  - cyclodextrins
KW  - molecular devices
KW  - host-guest systems
UR  - https://doi.org/10.1002/cphc.202000472
L2  - https://doi.org/10.1002/cphc.202000472
N2  - 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.
ER  -

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. \textit{ChemPhysChem}. Weinheim: Wiley, 2020, vol.~21, No~18, p.~2084-2095. ISSN~1439-4235. Available from: https://dx.doi.org/10.1002/cphc.202000472.

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