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.

Basic information

Original name

Hypervalent Iodine Based Reversible Covalent Bond in Rotaxane Synthesis

Authors

KANDRNÁLOVÁ, Markéta (203 Czech Republic, belonging to the institution), Zoran KOKAN (191 Croatia, belonging to the institution), Václav HAVEL (203 Czech Republic, belonging to the institution), Marek NEČAS (203 Czech Republic, belonging to the institution) and Vladimír ŠINDELÁŘ (203 Czech Republic, guarantor, belonging to the institution)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10400 1.4 Chemical sciences

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 12.959

RIV identification code

RIV/00216224:14310/19:00108208

Organization unit

Faculty of Science

DOI

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

UT WoS

000493165200001

Keywords in English

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

Abstract

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.

Links

EF16_013/0001761, research and development project

Name: RECETOX RI

GA18-21801S, research and development project

Name: Chirální bambusurily

Investor: Czech Science Foundation

LM2015043, research and development project

Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)

Investor: Ministry of Education, Youth and Sports of the CR

LM2015051, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX RI)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

KANDRNÁLOVÁ, Markéta, Zoran KOKAN, Václav HAVEL, Marek NEČAS and Vladimír ŠINDELÁŘ. Hypervalent Iodine Based Reversible Covalent Bond in Rotaxane Synthesis. Angewandte Chemie International Edition. WEINHEIM (GERMANY): Verlag Chemie, 2019, vol. 58, No 50, p. 18182-18185, 5 pp. ISSN 1433-7851. Available from: 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 and Vladimír ŠINDELÁŘ. Hypervalent Iodine Based Reversible Covalent Bond in Rotaxane Synthesis. \textit{Angewandte Chemie International Edition}. WEINHEIM (GERMANY): Verlag Chemie, 2019, vol.~58, No~50, p.~18182-18185, 5 pp. ISSN~1433-7851. Available from: https://dx.doi.org/10.1002/anie.201908953.

Detailed Information on Publication Record