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.

Základní údaje

Originální název

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

Autoři

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

Vydání

ChemPhysChem, Weinheim, Wiley, 2020, 1439-4235

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.102

Kód RIV

RIV/00216224:14740/20:00118083

Organizační jednotka

Středoevropský technologický institut

DOI

https://doi.org/10.1002/cphc.202000472

UT WoS

000563816800001

EID Scopus

2-s2.0-85089898024

Klíčová slova anglicky

stilbene switch; cucurbit[n]uril; cyclodextrins; molecular devices; host-guest systems

Štítky

14313010, CF CRYO, CF SAXS, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 27. 10. 2024 14:07, Ing. Martina Blahová

Anotace

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.

Návaznosti

LM2015085, projekt VaV

Název: CERIT Scientific Cloud (Akronym: CERIT-SC)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CERIT Scientific Cloud

LQ1601, projekt VaV

Název: CEITEC 2020 (Akronym: CEITEC2020)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CEITEC 2020

90042, velká výzkumná infrastruktura

Název: CESNET II

90070, velká výzkumná infrastruktura

Název: IT4Innovations

90127, velká výzkumná infrastruktura

Název: CIISB II

Citovat

KULKARNI, Shantanu Ganesh; Kristýna JELÍNKOVÁ; Marek NEČAS; Zdeňka PRUCKOVÁ; Michal ROUCHAL; Lenka DASTYCHOVÁ; Petr KULHÁNEK a Robert VÍCHA. A Photochemical/Thermal Switch Based on 4,4'-Bis(benzimidazolio)stilbene: Synthesis and Supramolecular Properties. ChemPhysChem. Weinheim: Wiley, 2020, roč. 21, č. 18, s. 2084-2095. ISSN 1439-4235. Dostupné z: https://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 = {https://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 a Robert VÍCHA. A Photochemical/Thermal Switch Based on 4,4'-Bis(benzimidazolio)stilbene: Synthesis and Supramolecular Properties. \textit{ChemPhysChem}. Weinheim: Wiley, 2020, roč.~21, č.~18, s.~2084-2095. ISSN~1439-4235. Dostupné z: https://doi.org/10.1002/cphc.202000472.

Přehled o publikaci