Binding study on 1-adamantylalkyl(benz)imidazolium salts to cyclodextrins and cucurbit[n]urils
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F20%3A63526120" target="_blank" >RIV/70883521:28110/20:63526120 - isvavai.cz</a>
Result on the web
<a href="https://pubs.rsc.org/en/content/articlelanding/2020/NJ/D0NJ00738B#!divAbstract" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2020/NJ/D0NJ00738B#!divAbstract</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d0nj00738b" target="_blank" >10.1039/d0nj00738b</a>
Alternative languages
Result language
angličtina
Original language name
Binding study on 1-adamantylalkyl(benz)imidazolium salts to cyclodextrins and cucurbit[n]urils
Original language description
Multitopic guests are used as key components of molecular triggers, switchers, sensors, or reactors in recent supramolecular chemistry studies. The increasing complexity of these compounds correlates with the need for versatile, synthetically available binding motifs (building blocks) with tuneable supramolecular properties. The utilisation of a favoured 1-adamantylmethyl moiety in ammonium, imidazolium and pyridinium salts is sometimes restricted by synthetic difficulties most likely related to the adamantane cage bulkiness. Therefore, we prepared a series of new adamantylated (benz)imidazolium salts with longer flexible linkers between the adamantane cage and cationic moiety. We tested the supramolecular properties of these binding motifs towards the natural cyclodextrins α-CD, β-CD and γ-CD and cucurbit[n]urils (n= 7, 8) using NMR, mass spectrometry and titration calorimetry. All tested guests formed 1:1 complexes with the abovementioned hosts, retaining binding strengths, selectivity, and complex geometries in comparison to the parent methylene-linked homologues. We did not confirm our original concern that longer linkers would negatively affect the binding strength towards CBns due to the reduction in the ion-dipole interaction contribution. Therefore, we believe that adamantylalkyl imidazolium binding motifs can be used for multitopic supramolecular guest construction.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
—
Continuities
S - Specificky vyzkum na vysokych skolach
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
NEW JOURNAL OF CHEMISTRY
ISSN
1144-0546
e-ISSN
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Volume of the periodical
44
Issue of the periodical within the volume
17
Country of publishing house
GB - UNITED KINGDOM
Number of pages
9
Pages from-to
7071-7079
UT code for WoS article
000532252100043
EID of the result in the Scopus database
2-s2.0-85084429923