pH Control on the Sequential Uptake and Release of Organic
Cations by Cucurbit[7]uril

J 2017

pH Control on the Sequential Uptake and Release of Organic Cations by Cucurbit[7]uril

MIKULŮ, Lukáš, Romana MICHALICOVÁ, Vivian IGLESIAS, Mirza Arfan YAWER, Angel KAIFER et. al.

Basic information

Original name

pH Control on the Sequential Uptake and Release of Organic Cations by Cucurbit[7]uril

Authors

MIKULŮ, Lukáš (203 Czech Republic, belonging to the institution), Romana MICHALICOVÁ (203 Czech Republic, belonging to the institution), Vivian IGLESIAS (840 United States of America), Mirza Arfan YAWER (586 Pakistan, belonging to the institution), Angel KAIFER (724 Spain), Přemysl LUBAL (203 Czech Republic, belonging to the institution) and Vladimír ŠINDELÁŘ (203 Czech Republic, guarantor, belonging to the institution)

Edition

Chemistry - A European Journal, WEINHEIM, WILEY-V C H VERLAG GMBH, 2017, 0947-6539

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 5.160

RIV identification code

RIV/00216224:14310/17:00094680

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1002/chem.201604417

UT WoS

000395583200018

Keywords in English

cage compounds; drug delivery; macrocycles; molecular devices; supramolecular chemistry

Abstract

V originále

Cucurbit[7]uril (CB7) is a macrocycle with the ability to form the most stable supramolecular complexes in water ever reported for an artificial receptor. Its use for the design of advanced functional materials is, however, very limited because there is no example of a fully reversible CB7 based supramolecular complex enabling repetitious dissociation/ association controlled by external stimuli. We report the synthesis of a new ferrocene amino acid that forms with CB7 a 1:1 inclusion complex that is stable in submicromolar concentration at low pH but dissociates at high pH. This reversible process was used for the sequential uptake and release of bispyridinium and antraquinone guests by CB7, which is controlled by adjusting the pH of the solution.

Links

GA13-15576S, research and development project

Name: Syntéza a supramolekulární vlastnosti bambusurilů

Investor: Czech Science Foundation

LM2011028, research and development project

Name: RECETOX ? Národní infrastruktura pro výzkum toxických látek v prostředí

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

LO1214, research and development project

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

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

LQ1601, research and development project

Name: CEITEC 2020 (Acronym: CEITEC2020)

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

Citovat

MIKULŮ, Lukáš, Romana MICHALICOVÁ, Vivian IGLESIAS, Mirza Arfan YAWER, Angel KAIFER, Přemysl LUBAL and Vladimír ŠINDELÁŘ. pH Control on the Sequential Uptake and Release of Organic Cations by Cucurbit[7]uril. Chemistry - A European Journal. WEINHEIM: WILEY-V C H VERLAG GMBH, 2017, vol. 23, No 10, p. 2350-2355. ISSN 0947-6539. Available from: https://dx.doi.org/10.1002/chem.201604417.

@article{1376060,
   author = {Mikulů, Lukáš and Michalicová, Romana and Iglesias, Vivian and Yawer, Mirza Arfan and Kaifer, Angel and Lubal, Přemysl and Šindelář, Vladimír},
   article_location = {WEINHEIM},
   article_number = {10},
   doi = {http://dx.doi.org/10.1002/chem.201604417},
   keywords = {cage compounds; drug delivery; macrocycles; molecular devices; supramolecular chemistry},
   language = {eng},
   issn = {0947-6539},
   journal = {Chemistry - A European Journal},
   title = {pH Control on the Sequential Uptake and Release of Organic Cations by Cucurbit[7]uril},
   url = {http://onlinelibrary.wiley.com/doi/10.1002/chem.201604417/abstract},
   volume = {23},
   year = {2017}
}

TY  - JOUR
ID  - 1376060
AU  - Mikulů, Lukáš - Michalicová, Romana - Iglesias, Vivian - Yawer, Mirza Arfan - Kaifer, Angel - Lubal, Přemysl - Šindelář, Vladimír
PY  - 2017
TI  - pH Control on the Sequential Uptake and Release of Organic Cations by Cucurbit[7]uril
JF  - Chemistry - A European Journal
VL  - 23
IS  - 10
SP  - 2350-2355
EP  - 2350-2355
PB  - WILEY-V C H VERLAG GMBH
SN  - 09476539
KW  - cage compounds
KW  - drug delivery
KW  - macrocycles
KW  - molecular devices
KW  - supramolecular chemistry
UR  - http://onlinelibrary.wiley.com/doi/10.1002/chem.201604417/abstract
L2  - http://onlinelibrary.wiley.com/doi/10.1002/chem.201604417/abstract
N2  - Cucurbit[7]uril (CB7) is a macrocycle with the ability to form the most stable supramolecular complexes in water ever reported for an artificial receptor. Its use for the design of advanced functional materials is, however, very limited because there is no example of a fully reversible CB7 based supramolecular complex enabling repetitious dissociation/ association controlled by external stimuli. We report the synthesis of a new ferrocene amino acid that forms with CB7 a 1:1 inclusion complex that is stable in submicromolar concentration at low pH but dissociates at high pH. This reversible process was used for the sequential uptake and release of bispyridinium and antraquinone guests by CB7, which is controlled by adjusting the pH of the solution.
ER  -

MIKULŮ, Lukáš, Romana MICHALICOVÁ, Vivian IGLESIAS, Mirza Arfan YAWER, Angel KAIFER, Přemysl LUBAL and Vladimír ŠINDELÁŘ. pH Control on the Sequential Uptake and Release of Organic Cations by Cucurbit[7]uril. \textit{Chemistry - A European Journal}. WEINHEIM: WILEY-V C H VERLAG GMBH, 2017, vol.~23, No~10, p.~2350-2355. ISSN~0947-6539. Available from: https://dx.doi.org/10.1002/chem.201604417.

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