| KANDRNÁLOVÁ, Markéta a Vladimír ŠINDELÁŘ. Cucurbiturils Monofunctionalized on the Methylene Bridge and Their Host-Guest Properties. European Journal of Organic Chemistry. Weinheim: WILEY-VCH, 2021, roč. 2021, č. 33, s. 4733-4736. ISSN 1434-193X. Dostupné z: https://dx.doi.org/10.1002/ejoc.202100705. |
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@article{1805314,
author = {Kandrnálová, Markéta and Šindelář, Vladimír},
article_location = {Weinheim},
article_number = {33},
doi = {http://dx.doi.org/10.1002/ejoc.202100705},
keywords = {Cucurbiturils; Host-guest complexes; Macrocycles; Monofunctionalization; Self-assembly},
language = {eng},
issn = {1434-193X},
journal = {European Journal of Organic Chemistry},
title = {Cucurbiturils Monofunctionalized on the Methylene Bridge and Their Host-Guest Properties},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202100705},
volume = {2021},
year = {2021}
}
TY - JOUR
ID - 1805314
AU - Kandrnálová, Markéta - Šindelář, Vladimír
PY - 2021
TI - Cucurbiturils Monofunctionalized on the Methylene Bridge and Their Host-Guest Properties
JF - European Journal of Organic Chemistry
VL - 2021
IS - 33
SP - 4733-4736
EP - 4733-4736
PB - WILEY-VCH
SN - 1434193X
KW - Cucurbiturils
KW - Host-guest complexes
KW - Macrocycles
KW - Monofunctionalization
KW - Self-assembly
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202100705
N2 - Monofunctionalization of cucurbiturils is essential for transferring these potent supramolecular macrocyclic hosts into real-world application. Here, we present the synthesis of cucurbit[6]urils 1 and 2 in which one methylene bridge is modified by a single substituent containing a nitro or an ammonium group. We investigated host-guest properties in water and 0.2 M NaCl using H-1 NMR and isothermal titration calorimetry, particularly for 2. The macrocycle 2 self-associated into dimeric aggregates in pure water, but readily disassembled in the presence of NaCl or organic cations. Cucurbit[7]uril was able to encapsulate the ammonium substituent of 2 inside its cavity resulting in a complex of 1 : 1 stoichiometry with an association constant of 3.1x10(5) M-1. The presented host-guest properties together with further possible derivatization showcase the potential of cucurbiturils modified in the methylene position such as 1 and 2 for the development of advanced supramolecular systems.
ER -
KANDRNÁLOVÁ, Markéta a Vladimír ŠINDELÁŘ. Cucurbiturils Monofunctionalized on the Methylene Bridge and Their Host-Guest Properties. \textit{European Journal of Organic Chemistry}. Weinheim: WILEY-VCH, 2021, roč.~2021, č.~33, s.~4733-4736. ISSN~1434-193X. Dostupné z: https://dx.doi.org/10.1002/ejoc.202100705.
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