Hydrogen‐Bonding‐Regulated Supramolecular Nanostructures and Impact on Multivalent Binding

Bonded with a purpose: Two bolaamphiphiles consisting of a hydrophobic naphthalene diimide unit connected at one end to a hydrophilic wedge by a H‐bonding group (hydrazide or amide) and at the other to a glucose moiety showed distinct H‐bonding‐regulated behavior with the formation of vesicles or cylindrical micelles (see picture). The adaptive cylindrical micelles formed by amide H‐bonding exhibited superior multivalent binding with concanavalin A.

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.

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