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.

Základní údaje

Originální název

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

Autoři

JELINKOVA, Kristyna, Aneta ZAVODNA, Jiri KALETA, Petr JANOVSKY, Filip ZATLOUKAL, Marek NEČAS (203 Česká republika, garant, domácí), Zdenka PRUCKOVA, Lenka DASTYCHOVA, Michal ROUCHAL a Robert VICHA

Vydání

Journal of Organic Chemistry, WASHINGTON, AMER CHEMICAL SOC, 2023, 0022-3263

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.600 v roce 2022

Kód RIV

RIV/00216224:14310/23:00132619

Organizační jednotka

Přírodovědecká fakulta

DOI

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

UT WoS

001092725700001

Klíčová slova anglicky

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

Štítky

CF BIC, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 15. 10. 2024 17:42, Ing. Marie Švancarová

Anotace

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.

Návaznosti

90242, velká výzkumná infrastruktura

Název: CIISB III

Citovat

JELINKOVA, Kristyna, Aneta ZAVODNA, Jiri KALETA, Petr JANOVSKY, Filip ZATLOUKAL, Marek NEČAS, Zdenka PRUCKOVA, Lenka DASTYCHOVA, Michal ROUCHAL a 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, roč. 88, č. 22, s. 15615-15625. ISSN 0022-3263. Dostupné z: 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 a 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, roč.~88, č.~22, s.~15615-15625. ISSN~0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.3c01556.

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