Synthesis of bambusurils with perfluoroalkylthiobenzyl groups as highly potent halide receptors

Result code in 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>

Result on the web

<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>

Result language

angličtina

Original language name

Synthesis of bambusurils with perfluoroalkylthiobenzyl groups as highly potent halide receptors

Original language description

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.

Czech name

—

Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10401 - Organic chemistry

Project

<a href="/en/project/GA23-05271S" target="_blank" >GA23-05271S: Chemical modification of bambusurils for adjusting their binding affinity and selectivity</a><br>

Continuities

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

Publication year

2025

Confidentiality

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

Name of the periodical

Organic Chemistry Frontiers

ISSN

2052-4129

e-ISSN

—

Volume of the periodical

12

Issue of the periodical within the volume

1

Country of publishing house

GB - UNITED KINGDOM

Number of pages

6

Pages from-to

130-135

UT code for WoS article

001345739800001

EID of the result in the Scopus database

2-s2.0-85208791935