Synthesis and Properties of pH-Responsive Imidazolium-based Guests

Kód výsledku v IS VaVaI

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Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and Properties of pH-Responsive Imidazolium-based Guests

Popis výsledku v původním jazyce

Guest molecules with multiple non-equivalent binding sites are recently extensively studied as important components for complex supramolecular systems. Compounds bearing protondissociable groups (e.g. carboxylate, amine), which pH-affected dissociation can change binding properties of entire molecule, are of a particular interest. Herein, we report a preparation of imidazolium-based guest consisting of adamantane cage, permanently charged (benz)imidazolium cation, and dissociable carboxylic group linkedto the (benz)imidazolium by C5 aliphatic chain. In addition, we examined the binding properties of new guest towards cucurbit[n]urils (CBn, n=6 and 7) and ?-/?-cyclodextrins (CD) using NMR, ITC and ESI-MS techniques. Since the sphere-like adamantane cage perfectly fits the interior of CB7 and ?-CD, these two hosts predominantly occupy the adamantane binding site. On the other hand, the interior cavity of ?-CD and CB6 is too small to include bulky adamantane moiety. Therefore, these host

Název v anglickém jazyce

Synthesis and Properties of pH-Responsive Imidazolium-based Guests

Popis výsledku anglicky

Guest molecules with multiple non-equivalent binding sites are recently extensively studied as important components for complex supramolecular systems. Compounds bearing protondissociable groups (e.g. carboxylate, amine), which pH-affected dissociation can change binding properties of entire molecule, are of a particular interest. Herein, we report a preparation of imidazolium-based guest consisting of adamantane cage, permanently charged (benz)imidazolium cation, and dissociable carboxylic group linkedto the (benz)imidazolium by C5 aliphatic chain. In addition, we examined the binding properties of new guest towards cucurbit[n]urils (CBn, n=6 and 7) and ?-/?-cyclodextrins (CD) using NMR, ITC and ESI-MS techniques. Since the sphere-like adamantane cage perfectly fits the interior of CB7 and ?-CD, these two hosts predominantly occupy the adamantane binding site. On the other hand, the interior cavity of ?-CD and CB6 is too small to include bulky adamantane moiety. Therefore, these host

Druh

O - Ostatní výsledky

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2015

Kód důvěrnosti údajů

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