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Hydrogen‐Bonding‐Regulated Supramolecular Nanostructures and Impact on Multivalent Binding
Author(s) -
Sikder Amrita,
Ray Debes,
Aswal Vinod K.,
Ghosh Suhrit
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201812217
Subject(s) - hydrogen bond , chemistry , supramolecular chemistry , micelle , vesicle , amphiphile , nanostructure , halogen bond , crystallography , supramolecular assembly , moiety , amide , stacking , stereochemistry , membrane , nanotechnology , materials science , organic chemistry , molecule , copolymer , polymer , aqueous solution , crystal structure , biochemistry
Abstract Herein we describe the H‐bonding‐regulated nanostructure, thermodynamics, and multivalent binding of two bolaamphiphiles NDI‐1 and NDI‐2 consisting of a hydrophobic naphthalene diimide connected to a hydrophilic wedge by a H‐bonding group and a glucose moiety on its two arms. NDI‐1 and NDI‐2 differ by the single H‐bonding group, namely, hydrazide or amide, which triggers the formation of vesicles and cylindrical micelles, respectively. Although the extended H‐bonding ensures stacking with head‐to‐head orientation and the formation of an array of the appended glucose moieties in both systems, the adaptive cylindrical structure exhibited superior multivalent binding with concanavalin A (ConA) to that of the vesicle. A control amphiphile lacking a H‐bonding group assembled with a random lateral orientation to produce spherical micelles without any notable multivalent binding.