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Interaction of Cyclodextrins with Amphiphilic Alternating Cooligomers Possessing the Dense Triazole Backbone

delete2024-03-20
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PRE
AI
T
Tomoaki Yamamoto
R
R. Taguchi
Z
Zijun Yan
R
Ryo Ejima
许琳琳 cover
许琳琳 (Linlin Xu)
M
Masaki Nakahata
Y
Yuri Kamon
A
Akihito Hashidzume *
DOI:10.1021/acs.langmuir.4c00330delete
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Abstract

Abstract

En 中文
The interaction of cyclodextrins (CDs) with structure-controlled polymers is expected to provide significant insights into macromolecular recognition. However, the interaction of CDs with structure-controlled polymers has been an underexamined issue of investigation. Herein, alternating amphiphilic cooligomers (oligoCnAH, where n denotes the carbon number of alkyl groups; n = 4, 8, and 12) were synthesized by copper(I)-catalyzed azide-alkyne cycloaddition polymerization of heterodimers of 4-azido-5-hexynoic acid (AH) derivatives carrying N-alkylamide and t-butyl (tBu) ester side chains, followed by hydrolysis of the tBu ester, to study the interaction of CDs with oligoCnAH by H-1 NMR, nuclear Overhauser effect spectroscopy, and pulse-field-gradient spin-echo NMR. These NMR studies indicated that alpha CD interacted with oligoC4AH, alpha CD and beta CD interacted with oligoC8AH, and all CDs interacted with oligoC12AH. Based on the equilibrium models proposed, the binding constants were evaluated for the binary mixtures, which showed interaction. Comparing the interactions of the CDs/oligoC12AH binary mixtures with those of the binary mixtures of CDs and alternating copolymers of sodium maleate and dodecyl vinyl ether (polyC12M), it is concluded that oligoC12AH forms less stable micelles than does polyC12M presumably because of the lower molecular weight, the hydrophilic amide groups in the side chain, and the longer interval between neighboring C12 groups in oligoC12AH.
Keywords:
MACROMOLECULAR RECOGNITION
SUPRAMOLECULAR HYDROGELS
MOLECULAR RECOGNITION
BETA-CYCLODEXTRIN
SODIUM MALEATE
COMPLEXATION
TRANSITION
ELASTOMERS
COPOLYMERS
SWITCHES

Journal

Langmuir cover
Langmuir
IF:
3.9
Papers:
5.4W
Citations:
10.6W

Organization

S
shanghai jiao tong university
Scholars:
15.2W
Papers: 11.5W
Citations: 159
T
the university of osaka
Scholars:
2.8W
Papers: 1.8W
Citations: 6