J 2016

A Cucurbituril Derivative That Exhibits Cation-Modulated Self Assembly

USTRNUL, Lukáš, Michal BABIAK, Petr KULHÁNEK and Vladimír ŠINDELÁŘ

Basic information

Original name

A Cucurbituril Derivative That Exhibits Cation-Modulated Self Assembly

Authors

USTRNUL, Lukáš (203 Czech Republic, belonging to the institution), Michal BABIAK (703 Slovakia, belonging to the institution), Petr KULHÁNEK (203 Czech Republic, belonging to the institution) and Vladimír ŠINDELÁŘ (203 Czech Republic, guarantor, belonging to the institution)

Edition

Journal of Organic Chemistry, WASHINGTON, AMER CHEMICAL SOC, 2016, 0022-3263

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

Impact factor

Impact factor: 4.849

RIV identification code

RIV/00216224:14310/16:00088096

Organization unit

Faculty of Science

UT WoS

000380181500028

Keywords (in Czech)

SUPRAMOLEKULÁRNÍ CHEMIE; CUCURBITURIL; SELF-ASOCIACE

Keywords in English

SUPRAMOLECULAR CHEMISTRY; CUCURBITURIL; SELF-ASSOCIATION

Tags

International impact, Reviewed
Změněno: 23/8/2016 15:21, Mgr. Lukáš Ustrnul, Ph.D.

Abstract

V originále

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.

Links

GA13-15576S, research and development project
Name: Syntéza a supramolekulární vlastnosti bambusurilů
Investor: Czech Science Foundation
LM2011028, research and development project
Name: RECETOX ? Národní infrastruktura pro výzkum toxických látek v prostředí
Investor: Ministry of Education, Youth and Sports of the CR
LM2015043, research and development project
Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)
Investor: Ministry of Education, Youth and Sports of the CR
LM2015085, research and development project
Name: CERIT Scientific Cloud (Acronym: CERIT-SC)
Investor: Ministry of Education, Youth and Sports of the CR, CERIT Scientific Cloud
LO1214, research and development project
Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX)
Investor: Ministry of Education, Youth and Sports of the CR