Functionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F20%3A00114331" target="_blank" >RIV/00216224:14310/20:00114331 - isvavai.cz</a>

Výsledek na webu

<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cplu.202000261" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cplu.202000261</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/cplu.202000261" target="_blank" >10.1002/cplu.202000261</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Functionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates

Popis výsledku v původním jazyce

Bambusurils are a class of macrocyclic anion receptors that exhibit notable anion recognition properties, able to bind various inorganic anions as well the carboxylates or sulfonates. Recently, we reported enantioselective recognition of chiral carboxylates using non-functionalized chiral bambusuril derivatives. Herein, we report the synthesis and host-guest properties of two new representatives of chiral bambusuril macrocycles bearing ester functional groups, differing by the substituents attached to their portals. Their supramolecular properties in terms of carboxylate binding were studied by means of NMR in DMSO-d(6). The reported bambusurils bind selected chiral carboxylates with enantioselectivity factors up to 3.1. The results indicated that the selectivity towards different carboxylates is governed by the steric constraint of the substituents surrounding bambusuril portals. No clear trend in the binding affinities and their enantioselectivities was found.

Název v anglickém jazyce

Functionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates

Popis výsledku anglicky

Bambusurils are a class of macrocyclic anion receptors that exhibit notable anion recognition properties, able to bind various inorganic anions as well the carboxylates or sulfonates. Recently, we reported enantioselective recognition of chiral carboxylates using non-functionalized chiral bambusuril derivatives. Herein, we report the synthesis and host-guest properties of two new representatives of chiral bambusuril macrocycles bearing ester functional groups, differing by the substituents attached to their portals. Their supramolecular properties in terms of carboxylate binding were studied by means of NMR in DMSO-d(6). The reported bambusurils bind selected chiral carboxylates with enantioselectivity factors up to 3.1. The results indicated that the selectivity towards different carboxylates is governed by the steric constraint of the substituents surrounding bambusuril portals. No clear trend in the binding affinities and their enantioselectivities was found.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10400 - Chemical sciences

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2020

Kód důvěrnosti údajů

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

Název periodika

CHEMPLUSCHEM

ISSN

2192-6506

e-ISSN

—

Svazek periodika

85

Číslo periodika v rámci svazku

6

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

8

Strana od-do

1307-1314

Kód UT WoS článku

000544057700025

EID výsledku v databázi Scopus

2-s2.0-85086713149