Hypervalent Iodine Based Reversible Covalent Bond in Rotaxane
Synthesis

J 2019

Hypervalent Iodine Based Reversible Covalent Bond in Rotaxane Synthesis

KANDRNÁLOVÁ, Markéta, Zoran KOKAN, Václav HAVEL, Marek NEČAS, Vladimír ŠINDELÁŘ et. al.

Základní údaje

Originální název

Hypervalent Iodine Based Reversible Covalent Bond in Rotaxane Synthesis

Autoři

KANDRNÁLOVÁ, Markéta (203 Česká republika, domácí), Zoran KOKAN (191 Chorvatsko, domácí), Václav HAVEL (203 Česká republika, domácí), Marek NEČAS (203 Česká republika, domácí) a Vladimír ŠINDELÁŘ (203 Česká republika, garant, domácí)

Vydání

Angewandte Chemie International Edition, WEINHEIM (GERMANY), Verlag Chemie, 2019, 1433-7851

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 12.959

Kód RIV

RIV/00216224:14310/19:00108208

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1002/anie.201908953

UT WoS

000493165200001

Klíčová slova anglicky

anion receptors; bambusurils; dynamic covalent bonds; macrocycles; rotaxanes

Štítky

CF PROT, CF SAXS, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 17. 2. 2023 21:27, Mgr. Michaela Hylsová, Ph.D.

Anotace

V originále

Reversible covalent bonds play a significant role in achieving the high-yielding synthesis of mechanically interlocked molecules. Still, only a handful of such bonds have been successfully employed in synthetic procedures. Herein, we introduce a novel approach for the fast and simple preparation of interlocked molecules, combining the dynamic bond character of bis(acyloxy)iodate(I) anions with macrocyclic bambusuril anion receptors. The proof of principle was demonstrated on rotaxane synthesis, with near-quantitative yields observed in both the classical and "in situ" approach. The rotaxane formation was confirmed in the solid-state and solution by the X-ray and NMR studies. Our novel approach could be utilized in the fields of dynamic combinatorial chemistry, supramolecular polymers, or molecular machines, as well inspire further research on molecules that exhibit dynamic behavior, but owing to their high reactivity, have not been considered as constituents of more elaborate supramolecular structures.

Návaznosti

EF16_013/0001761, projekt VaV

Název: RECETOX RI

GA18-21801S, projekt VaV

Název: Chirální bambusurily

Investor: Grantová agentura ČR, Chirální bambusurily

LM2015043, projekt VaV

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

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

LM2015051, projekt VaV

Název: Centrum pro výzkum toxických látek v prostředí (Akronym: RECETOX RI)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Výzkumná infrastruktura RECETOX

Citovat

KANDRNÁLOVÁ, Markéta, Zoran KOKAN, Václav HAVEL, Marek NEČAS a Vladimír ŠINDELÁŘ. Hypervalent Iodine Based Reversible Covalent Bond in Rotaxane Synthesis. Angewandte Chemie International Edition. WEINHEIM (GERMANY): Verlag Chemie, 2019, roč. 58, č. 50, s. 18182-18185, 5 s. ISSN 1433-7851. Dostupné z: https://dx.doi.org/10.1002/anie.201908953.

@article{1639898,
   author = {Kandrnálová, Markéta and Kokan, Zoran and Havel, Václav and Nečas, Marek and Šindelář, Vladimír},
   article_location = {WEINHEIM (GERMANY)},
   article_number = {50},
   doi = {http://dx.doi.org/10.1002/anie.201908953},
   keywords = {anion receptors; bambusurils; dynamic covalent bonds; macrocycles; rotaxanes},
   language = {eng},
   issn = {1433-7851},
   journal = {Angewandte Chemie International Edition},
   title = {Hypervalent Iodine Based Reversible Covalent Bond in Rotaxane Synthesis},
   url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201908953},
   volume = {58},
   year = {2019}
}

TY  - JOUR
ID  - 1639898
AU  - Kandrnálová, Markéta - Kokan, Zoran - Havel, Václav - Nečas, Marek - Šindelář, Vladimír
PY  - 2019
TI  - Hypervalent Iodine Based Reversible Covalent Bond in Rotaxane Synthesis
JF  - Angewandte Chemie International Edition
VL  - 58
IS  - 50
SP  - 18182-18185
EP  - 18182-18185
PB  - Verlag Chemie
SN  - 14337851
KW  - anion receptors
KW  - bambusurils
KW  - dynamic covalent bonds
KW  - macrocycles
KW  - rotaxanes
UR  - https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201908953
L2  - https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201908953
N2  - Reversible covalent bonds play a significant role in achieving the high-yielding synthesis of mechanically interlocked molecules. Still, only a handful of such bonds have been successfully employed in synthetic procedures. Herein, we introduce a novel approach for the fast and simple preparation of interlocked molecules, combining the dynamic bond character of bis(acyloxy)iodate(I) anions with macrocyclic bambusuril anion receptors. The proof of principle was demonstrated on rotaxane synthesis, with near-quantitative yields observed in both the classical and "in situ" approach. The rotaxane formation was confirmed in the solid-state and solution by the X-ray and NMR studies. Our novel approach could be utilized in the fields of dynamic combinatorial chemistry, supramolecular polymers, or molecular machines, as well inspire further research on molecules that exhibit dynamic behavior, but owing to their high reactivity, have not been considered as constituents of more elaborate supramolecular structures.
ER  -

KANDRNÁLOVÁ, Markéta, Zoran KOKAN, Václav HAVEL, Marek NEČAS a Vladimír ŠINDELÁŘ. Hypervalent Iodine Based Reversible Covalent Bond in Rotaxane Synthesis. \textit{Angewandte Chemie International Edition}. WEINHEIM (GERMANY): Verlag Chemie, 2019, roč.~58, č.~50, s.~18182-18185, 5 s. ISSN~1433-7851. Dostupné z: https://dx.doi.org/10.1002/anie.201908953.

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