A Cucurbituril Derivative That Exhibits Cation-Modulated Self Assembly

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F16%3A00088096" target="_blank" >RIV/00216224:14310/16:00088096 - isvavai.cz</a>

Výsledek na webu

<a href="http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b01288" target="_blank" >http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b01288</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.joc.6b01288" target="_blank" >10.1021/acs.joc.6b01288</a>

Jazyk výsledku

angličtina

Název v původním jazyce

A Cucurbituril Derivative That Exhibits Cation-Modulated Self Assembly

Popis výsledku v původním jazyce

Cucurbiturils are the most potent artificial receptors known for many organic molecules in water. However, little is known about their supramolecular chemistry in organic solvents. Here we present a new cucurbituril derivative, 1, and investigate its supramolecular properties in methanol. The macrocycle resembles a five -membered cucurbituril in which four glycoluril units are replaced with propanediurea. Macrocyde 1 can bind to one cation such as potassium or anilinium via each of its opposed portals. The stability of these complexes in methanol at nanomolar concentrations exceeds that of complexes between metal cations and crown ethers. Moreover, macrocycle 1 forms a self -assembled tetrameric aggregate in the solid state and in methanol. The tetramer is stabilized by the addition of up to 1 equiv of a cation but is fully disassembled in the presence of 2 equiv of the cation. Cations can thus be used to tune the aggregation of 1 in solution.

Název v anglickém jazyce

A Cucurbituril Derivative That Exhibits Cation-Modulated Self Assembly

Popis výsledku anglicky

Cucurbiturils are the most potent artificial receptors known for many organic molecules in water. However, little is known about their supramolecular chemistry in organic solvents. Here we present a new cucurbituril derivative, 1, and investigate its supramolecular properties in methanol. The macrocycle resembles a five -membered cucurbituril in which four glycoluril units are replaced with propanediurea. Macrocyde 1 can bind to one cation such as potassium or anilinium via each of its opposed portals. The stability of these complexes in methanol at nanomolar concentrations exceeds that of complexes between metal cations and crown ethers. Moreover, macrocycle 1 forms a self -assembled tetrameric aggregate in the solid state and in methanol. The tetramer is stabilized by the addition of up to 1 equiv of a cation but is fully disassembled in the presence of 2 equiv of the cation. Cations can thus be used to tune the aggregation of 1 in solution.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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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)

Rok uplatnění

2016

Kód důvěrnosti údajů

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

Název periodika

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

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Svazek periodika

81

Číslo periodika v rámci svazku

14

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

6

Strana od-do

6075-6080

Kód UT WoS článku

000380181500028

EID výsledku v databázi Scopus

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