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@article{1352242,
author = {Ustrnul, Lukáš and Babiak, Michal and Kulhánek, Petr and Šindelář, Vladimír},
article_location = {WASHINGTON},
article_number = {14},
doi = {http://dx.doi.org/10.1021/acs.joc.6b01288},
keywords = {SUPRAMOLECULAR CHEMISTRY; CUCURBITURIL; SELF-ASSOCIATION},
language = {eng},
issn = {0022-3263},
journal = {Journal of Organic Chemistry},
title = {A Cucurbituril Derivative That Exhibits Cation-Modulated Self Assembly},
url = {http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b01288},
volume = {81},
year = {2016}
}
TY - JOUR
ID - 1352242
AU - Ustrnul, Lukáš - Babiak, Michal - Kulhánek, Petr - Šindelář, Vladimír
PY - 2016
TI - A Cucurbituril Derivative That Exhibits Cation-Modulated Self Assembly
JF - Journal of Organic Chemistry
VL - 81
IS - 14
SP - 6075-6080
EP - 6075-6080
PB - AMER CHEMICAL SOC
SN - 00223263
KW - SUPRAMOLECULAR CHEMISTRY
KW - CUCURBITURIL
KW - SELF-ASSOCIATION
UR - http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b01288
L2 - http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b01288
N2 - 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.
ER -
USTRNUL, Lukáš, Michal BABIAK, Petr KULHÁNEK and Vladimír ŠINDELÁŘ. A Cucurbituril Derivative That Exhibits Cation-Modulated Self Assembly. \textit{Journal of Organic Chemistry}. WASHINGTON: AMER CHEMICAL SOC, vol.~81, No~14, p.~6075-6080. ISSN~0022-3263. doi:10.1021/acs.joc.6b01288. 2016.
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