Cucurbiturils Monofunctionalized on the Methylene Bridge and
Their Host-Guest Properties

J 2021

Cucurbiturils Monofunctionalized on the Methylene Bridge and Their Host-Guest Properties

KANDRNÁLOVÁ, Markéta a Vladimír ŠINDELÁŘ

Základní údaje

Originální název

Cucurbiturils Monofunctionalized on the Methylene Bridge and Their Host-Guest Properties

Autoři

KANDRNÁLOVÁ, Markéta a Vladimír ŠINDELÁŘ

Vydání

European Journal of Organic Chemistry, Weinheim, WILEY-VCH, 2021, 1434-193X

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.261

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/21:00119375

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

Cucurbiturils; Host-guest complexes; Macrocycles; Monofunctionalization; Self-assembly

Štítky

143180, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 8. 6. 2025 14:16, Mgr. Michaela Hylsová, Ph.D.

Anotace

V originále

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.

Návaznosti

EF17_043/0009632, projekt VaV

Název: CETOCOEN Excellence

GA20-13922S, projekt VaV

Název: Monofunkcializované bambusurily a jejich supramolekulární vlastnosti

Investor: Grantová agentura ČR, Monofunkcializované bambusurily a jejich supramolekulární vlastnosti

LM2018127, projekt VaV

Název: Česká infrastruktura pro integrativní strukturní biologii (Akronym: CIISB)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Czech Infrastructure for Integrative Structural Biology

90121, velká výzkumná infrastruktura

Název: RECETOX RI

Citovat

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://doi.org/10.1002/ejoc.202100705.

@article{1805314,
   author = {Kandrnálová, Markéta and Šindelář, Vladimír},
   article_location = {Weinheim},
   article_number = {33},
   doi = {https://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://doi.org/10.1002/ejoc.202100705.

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