Synthesis of bambusurils with perfluoroalkylthiobenzyl groups as highly potent halide receptors

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F25%3A00140539" target="_blank" >RIV/00216224:14310/25:00140539 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlelanding/2025/qo/d4qo01746c" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2025/qo/d4qo01746c</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d4qo01746c" target="_blank" >10.1039/d4qo01746c</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of bambusurils with perfluoroalkylthiobenzyl groups as highly potent halide receptors

Popis výsledku v původním jazyce

The preparation of anion receptors with ultrahigh binding affinities is an important, yet challenging, topic of supramolecular chemistry. The search for new structural motifs which would enhance the performance of anion receptors is therefore an important task. In this context, we report the synthesis of novel fluorinated bambus[6]urils that incorporate unique benzyl substituents with perfluoroalkylthio groups, aimed at enhancing their anion receptor capabilities. The synthetic strategy developed allows for the efficient preparation of these structural motifs. Ultrahigh stability of the complexes between halides and the prepared bambus[6]urils was observed and quantified using F-19 NMR competition experiments. Replacing -CF3 groups on benzylated bambus[6]urils by -SCF3 groups increased the affinity of the macrocycles towards anions and provided the strongest iodide receptor reported with a binding affinity of 4 x 10(13) M-1 in acetonitrile.

Název v anglickém jazyce

Synthesis of bambusurils with perfluoroalkylthiobenzyl groups as highly potent halide receptors

Popis výsledku anglicky

The preparation of anion receptors with ultrahigh binding affinities is an important, yet challenging, topic of supramolecular chemistry. The search for new structural motifs which would enhance the performance of anion receptors is therefore an important task. In this context, we report the synthesis of novel fluorinated bambus[6]urils that incorporate unique benzyl substituents with perfluoroalkylthio groups, aimed at enhancing their anion receptor capabilities. The synthetic strategy developed allows for the efficient preparation of these structural motifs. Ultrahigh stability of the complexes between halides and the prepared bambus[6]urils was observed and quantified using F-19 NMR competition experiments. Replacing -CF3 groups on benzylated bambus[6]urils by -SCF3 groups increased the affinity of the macrocycles towards anions and provided the strongest iodide receptor reported with a binding affinity of 4 x 10(13) M-1 in acetonitrile.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA23-05271S" target="_blank" >GA23-05271S: Chemická modifikace bambusurilů pro úpravu jejich vazebné afinity a selektivity</a><br>

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

2025

Kód důvěrnosti údajů

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

Název periodika

Organic Chemistry Frontiers

ISSN

2052-4129

e-ISSN

—

Svazek periodika

12

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

6

Strana od-do

130-135

Kód UT WoS článku

001345739800001

EID výsledku v databázi Scopus

2-s2.0-85208791935