Two Squares in a Barrel: An Axially Disubstituted
Conformationally Rigid Aliphatic Binding Motif for
Cucurbit[6]uril

J 2023

Two Squares in a Barrel: An Axially Disubstituted Conformationally Rigid Aliphatic Binding Motif for Cucurbit[6]uril

JELINKOVA, Kristyna, Aneta ZAVODNA, Jiri KALETA, Petr JANOVSKY, Filip ZATLOUKAL et. al.

Basic information

Original name

Two Squares in a Barrel: An Axially Disubstituted Conformationally Rigid Aliphatic Binding Motif for Cucurbit[6]uril

Authors

JELINKOVA, Kristyna, Aneta ZAVODNA, Jiri KALETA, Petr JANOVSKY, Filip ZATLOUKAL, Marek NEČAS (203 Czech Republic, guarantor, belonging to the institution), Zdenka PRUCKOVA, Lenka DASTYCHOVA, Michal ROUCHAL and Robert VICHA

Edition

Journal of Organic Chemistry, WASHINGTON, AMER CHEMICAL SOC, 2023, 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:

URL

Impact factor

Impact factor: 3.600 in 2022

RIV identification code

RIV/00216224:14310/23:00132619

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acs.joc.3c01556

UT WoS

001092725700001

Keywords in English

HOST-GUEST BINDING; AFFINITY; MOVEMENT; ROTAXANE; SENSOR; CAVITY; MODES; SALTS

Abstract

V originále

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.

Links

90242, large research infrastructures

Name: CIISB III

Citovat

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. 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.

@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.

Detailed Information on Publication Record