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Issue 26, 2017
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Aqueous dispersions of nanostructures formed through the self-assembly of iminolipids with exchangeable hydrophobic termini

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Abstract

The addition of amines to an aldehyde surfactant, which was designed to be analogous to didodecyldimethylammonium bromide, gave exchangeable “iminolipids” that self-assembled to give stable aqueous dispersions of nano-sized vesicles. For example, sonication of suspensions of the n-hexylamine-derived iminolipid gave vesicles 50 to 200 nm in diameter that could encapsulate a water-soluble dye. The iminolipids could undergo dynamic exchange with added amines, and the resulting equilibrium constants (Krel) were quantified by 1H NMR spectroscopy. In the absence of lipid self-assembly, in CDCl3, the assayed primary amines gave very similar Krel values. However in D2O the value of Krel generally increased with increasing amine hydrophobicity, consistent with partitioning into a self-assembled bilayer. Amines with aromatic groups showed significantly higher values of Krel in D2O compared to similarly hydrophobic alkylamines, suggesting that π–π interactions favor lipid self-assembly. Given this synergistic relationship, π-rich pyrenyliminolipids were created and used to exfoliate graphite, leading to aqueous dispersions of graphene flakes that were stable over several months.

Graphical abstract: Aqueous dispersions of nanostructures formed through the self-assembly of iminolipids with exchangeable hydrophobic termini

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Supplementary files

Article information


Submitted
02 May 2017
Accepted
15 Jun 2017
First published
15 Jun 2017

Phys. Chem. Chem. Phys., 2017,19, 17036-17043
Article type
Paper

Aqueous dispersions of nanostructures formed through the self-assembly of iminolipids with exchangeable hydrophobic termini

W. Li, D. McManus, H. Liu, C. Casiraghi and S. J. Webb, Phys. Chem. Chem. Phys., 2017, 19, 17036
DOI: 10.1039/C7CP02868G

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