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@article{2352419,
author = {Jelinkova, Kristyna and Zavodna, Aneta and Kaleta, Jiri and Janovsky, Petr and Zatloukal, Filip and Nečas, Marek and Pruckova, Zdenka and Dastychova, Lenka and Rouchal, Michal and Vicha, Robert},
article_location = {WASHINGTON},
article_number = {22},
doi = {http://dx.doi.org/10.1021/acs.joc.3c01556},
keywords = {HOST-GUEST BINDING; AFFINITY; MOVEMENT; ROTAXANE; SENSOR; CAVITY; MODES; SALTS},
language = {eng},
issn = {0022-3263},
journal = {Journal of Organic Chemistry},
title = {Two Squares in a Barrel: An Axially Disubstituted Conformationally Rigid Aliphatic Binding Motif for Cucurbit[6]uril},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.3c01556},
volume = {88},
year = {2023}
}
TY - JOUR
ID - 2352419
AU - Jelinkova, Kristyna - Zavodna, Aneta - Kaleta, Jiri - Janovsky, Petr - Zatloukal, Filip - Nečas, Marek - Pruckova, Zdenka - Dastychova, Lenka - Rouchal, Michal - Vicha, Robert
PY - 2023
TI - Two Squares in a Barrel: An Axially Disubstituted Conformationally Rigid Aliphatic Binding Motif for Cucurbit[6]uril
JF - Journal of Organic Chemistry
VL - 88
IS - 22
SP - 15615-15625
EP - 15615-15625
PB - AMER CHEMICAL SOC
SN - 00223263
KW - HOST-GUEST BINDING
KW - AFFINITY
KW - MOVEMENT
KW - ROTAXANE
KW - SENSOR
KW - CAVITY
KW - MODES
KW - SALTS
UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c01556
N2 - Novel binding motifs suitable for the construction of multitopic guest-based molecular devices (e.g., switches, sensors, data storage, and catalysts) are needed in supramolecular chemistry. No rigid, aliphatic binding motif that allows for axial disubstitution has been described for cucurbit[6]uril (CB6) so far. We prepared three model guests combining spiro[3.3]heptane and bicyclo[1.1.1]pentane centerpieces with imidazolium and ammonium termini. We described their binding properties toward CB6/7 and alpha-/beta-CD using NMR, titration calorimetry, mass spectrometry, and single-crystal X-ray diffraction. We found that a bisimidazolio spiro[3.3]heptane guest forms inclusion complexes with CB6, CB7, and beta-CD with respective association constants of 4.0 x 10(4), 1.2 x 10(12), and 1.4 x 10(2). Due to less hindering terminal groups, the diammonio analogue forms more stable complexes with CB6 (K = 1.4 x 10(6)) and CB7 (K = 3.8 x 10(12)). The bisimidazolio bicyclo[1.1.1]pentane guest forms a highly stable complex only with CB7 with a K value of 1.1 x 10(11). The high selectivity of the new binding motifs implies promising potential in the construction of multitopic supramolecular components.
ER -
JELINKOVA, Kristyna, Aneta ZAVODNA, Jiri KALETA, Petr JANOVSKY, Filip ZATLOUKAL, Marek NEČAS, Zdenka PRUCKOVA, Lenka DASTYCHOVA, Michal ROUCHAL and Robert VICHA. Two Squares in a Barrel: An Axially Disubstituted Conformationally Rigid Aliphatic Binding Motif for Cucurbit[6]uril. \textit{Journal of Organic Chemistry}. WASHINGTON: AMER CHEMICAL SOC, 2023, vol.~88, No~22, p.~15615-15625. ISSN~0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.3c01556.
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