Dimeric molecular clips based on glycoluril

J 2017

Dimeric molecular clips based on glycoluril

SOKOLOV, Jan, Tomáš LÍZAL and Vladimír ŠINDELÁŘ

Basic information

Original name

Dimeric molecular clips based on glycoluril

Authors

SOKOLOV, Jan (203 Czech Republic, belonging to the institution), Tomáš LÍZAL (203 Czech Republic, belonging to the institution) and Vladimír ŠINDELÁŘ (203 Czech Republic, guarantor, belonging to the institution)

Edition

New Journal of Chemistry, Cambridge, ROYAL SOC. CHEMISTRY, 2017, 1144-0546

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 3.201

RIV identification code

RIV/00216224:14310/17:00095287

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1039/c7nj00969k

UT WoS

000405276100008

Keywords in English

CUCURBITURIL HOMOLOGS; DERIVATIVES; RECOGNITION; CHEMISTRY; FAMILY; WATER; N=5

Abstract

V originále

Glycoluril dimers 4a and 4b were prepared and successfully transformed to glycoluril dimeric clips 7a and 7b. H-1 NMR spectroscopy was used to reveal that the dimeric clip 7b with methyl substituents in its structure exists as a mixture of two distinct conformers in D2O at ambient temperature, while 7a possesses only one stable conformer under the same conditions due to its bulky phenyl substituents. The coalescence temperatures for 7b and its precursor 5b were determined. Both dimeric clips 7a and 7b formed complexes with methylviologen in D2O in which each of two clip-binding sites was occupied by one molecule of the guest. Thus, this study uncovers possible use of glycoluril dimers 4a and 4b as general building blocks for glycoluril-based supramolecular host molecules with two binding sites in their structure.

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

Citovat

SOKOLOV, Jan, Tomáš LÍZAL and Vladimír ŠINDELÁŘ. Dimeric molecular clips based on glycoluril. New Journal of Chemistry. Cambridge: ROYAL SOC. CHEMISTRY, 2017, vol. 41, No 14, p. 6105-6111. ISSN 1144-0546. Available from: https://dx.doi.org/10.1039/c7nj00969k.

@article{1400358,
   author = {Sokolov, Jan and Lízal, Tomáš and Šindelář, Vladimír},
   article_location = {Cambridge},
   article_number = {14},
   doi = {http://dx.doi.org/10.1039/c7nj00969k},
   keywords = {CUCURBITURIL HOMOLOGS; DERIVATIVES; RECOGNITION; CHEMISTRY; FAMILY; WATER; N=5},
   language = {eng},
   issn = {1144-0546},
   journal = {New Journal of Chemistry},
   title = {Dimeric molecular clips based on glycoluril},
   url = {http://pubs.rsc.org/en/Content/ArticleLanding/2017/NJ/C7NJ00969K#!divAbstract},
   volume = {41},
   year = {2017}
}

TY  - JOUR
ID  - 1400358
AU  - Sokolov, Jan - Lízal, Tomáš - Šindelář, Vladimír
PY  - 2017
TI  - Dimeric molecular clips based on glycoluril
JF  - New Journal of Chemistry
VL  - 41
IS  - 14
SP  - 6105-6111
EP  - 6105-6111
PB  - ROYAL SOC. CHEMISTRY
SN  - 11440546
KW  - CUCURBITURIL HOMOLOGS
KW  - DERIVATIVES
KW  - RECOGNITION
KW  - CHEMISTRY
KW  - FAMILY
KW  - WATER
KW  - N=5
UR  - http://pubs.rsc.org/en/Content/ArticleLanding/2017/NJ/C7NJ00969K#!divAbstract
L2  - http://pubs.rsc.org/en/Content/ArticleLanding/2017/NJ/C7NJ00969K#!divAbstract
N2  - Glycoluril dimers 4a and 4b were prepared and successfully transformed to glycoluril dimeric clips 7a and 7b. H-1 NMR spectroscopy was used to reveal that the dimeric clip 7b with methyl substituents in its structure exists as a mixture of two distinct conformers in D2O at ambient temperature, while 7a possesses only one stable conformer under the same conditions due to its bulky phenyl substituents. The coalescence temperatures for 7b and its precursor 5b were determined. Both dimeric clips 7a and 7b formed complexes with methylviologen in D2O in which each of two clip-binding sites was occupied by one molecule of the guest. Thus, this study uncovers possible use of glycoluril dimers 4a and 4b as general building blocks for glycoluril-based supramolecular host molecules with two binding sites in their structure.
ER  -

SOKOLOV, Jan, Tomáš LÍZAL and Vladimír ŠINDELÁŘ. Dimeric molecular clips based on glycoluril. \textit{New Journal of Chemistry}. Cambridge: ROYAL SOC. CHEMISTRY, 2017, vol.~41, No~14, p.~6105-6111. ISSN~1144-0546. Available from: https://dx.doi.org/10.1039/c7nj00969k.

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