Binding study on 1-adamantylalkyl(benz)imidazolium salts to cyclodextrins and cucurbit[n]urils

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Binding study on 1-adamantylalkyl(benz)imidazolium salts to cyclodextrins and cucurbit[n]urils

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Binding study on 1-adamantylalkyl(benz)imidazolium salts to cyclodextrins and cucurbit[n]urils

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2020

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

NEW JOURNAL OF CHEMISTRY

ISSN

1144-0546

e-ISSN

—

Svazek periodika

44

Číslo periodika v rámci svazku

17

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

7071-7079

Kód UT WoS článku

000532252100043

EID výsledku v databázi Scopus

2-s2.0-85084429923