Control of Guest Inclusion and Chiral Recognition Ability of 6-O-Modified β-Cyclodextrins in Organic Solvents by Aromatic Substituents at the 2-O Position.
chiral recognition
cyclodextrins
inclusion complexes
nonpolar solvents
polyaromatic compounds
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
08 2020
08 2020
Historique:
received:
09
07
2020
revised:
08
08
2020
entrez:
29
8
2020
pubmed:
29
8
2020
medline:
29
8
2020
Statut:
ppublish
Résumé
The host-guest chemistry and applications of cyclodextrins in aqueous media is well established. However, a comprehensive study in organic solvents is lacking. Here, we report the design and synthesis of 6-O-tert-butyldimethylsilylated β-cyclodextrin (TBDMS-β-CD) bearing various aromatic substitutions at the 2-O position and their inclusion complex formation with aromatic guests in nonpolar organic solvents. Compared to the parent TBDMS-β-CD, these derivatives exhibit at least a 10-fold increase in inclusion ability toward pyrene through cooperative guest binding with the CD cavity and the aromatic substituents at the 2-O position. The type of the aromatic substituent largely affects the chiral recognition ability of TBDMS-β-CD toward 1-(1-naphthyl)ethylamine in cyclohexane. A TBDMS-β-CD derivative with a p-tolyl substituent has a remarkable chiral selectivity for the (S)-1-(1-naphthyl)ethylamine over the corresponding (R)-isomer (K
Identifiants
pubmed: 32856786
doi: 10.1002/cplu.202000522
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1928-1933Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036.
K. E. Krakowiak, J. S. Bradshaw, D. J. Zamecka-Krakowiak, Chem. Rev. 1989, 89, 929-972.
J. E. Richman, T. J. Atkins, J. Am. Chem. Soc. 1974, 96, 2268-2270.
J. S. Kim, D. T. Quang, Chem. Rev., 2007, 107, 3780-3799.
C. Wieser, C. B. Dieleman, D. Matt, Coord. Chem. Rev. 1997, 165, 93-161.
W. Gerhard, Angew. Chem. Int. Ed. 1994, 33, 803-822;
Angew. Chem. 1994, 106, 851-870;
Comprehensive Supramolecular Chemistry, Vol. 3 (Eds.: J. Szejtli, T. Osa), Pergamon, Oxford, 1996;
Cyclodextrins and Their Complexes (Ed.: H. Dodziuk), Wiley-VCH, Weinheim, 2006;
G. Crini, Chem. Rev. 2014, 114, 10940-10975.
F. M. Menger, M. A. Dulany, Tetrahedron Lett. 1985, 26, 267-270.
T. Kida, Y. Fujino, K. Miyawaki, E. Kato, M. Akashi, Org. Lett. 2009, 11, 5282-5285.
T. Kida, T. Iwamoto, Y. Fujino, N. Tohnai, M. Miyata, M. Akashi, Org. Lett. 2011, 13, 4570-4573.
T. Kida, T. Iwamoto, H. Asahara, T. Hinoue, M. Akashi, J. Am. Chem. Soc. 2013, 135, 3371-3374.
H. Asahara, T. Kida, T. Iwamoto, T. Hinoue, M. Akashi, Tetrahedron 2014, 70, 197-203.
G. Gokel, Chem. Soc. Rev. 1992, 21, 39-47.
C. Asahara, T. Iwamoto, M. Akashi, H. Shigemitsu, T. Kida, ChemPlusChem 2018, 83, 868-873.
K. Takeo, H. Mitoh, K. Uemura, Carbohydr. Res. 1989, 187, 203-221.