Issue 3, 2022

Dissymmetrical tails-regulated helical nanoarchitectonics of amphiphilic ornithines: nanotubes, bundles and twists

Abstract

How dissymmetrical tails (i.e. tails of different lengths) in one lipid molecule exert an impact on the structure and properties of the resulting assembly is an intriguing issue in both biological and material senses. However, the underlying mechanism that engenders such phenomena is still obscure, which prompted us to unmask it by exploring the self-assembly behaviours of artificial building blocks comprising dissymmetrical tails. Here, a series of Fmoc-protected ornithine lipids with dissymmetrical alkyl tails was designed and the dissymmetry of the two tails was found to hierarchically tune the self-assembled nanostructures from nanotubes to bundles and nanotwists. With the Fmoc-headgroup employed as a chromophorous probe, it was revealed that the alkyl chain dissymmetry controlled the interacting modes of van der Waals interactions between alkyl tails, π–π stacking between Fmoc motifs and hydrogen bonding formed by the three amide bonds in lipid bilayers. The counterbalance between those noncovalent interactions was responsible for such remarkable tuning ability towards self-assembly and emissive behaviours of the lipids, including circularly polarized light emission. This work provides insight into dissymmetrical tails-regulated biological structures and functions of natural lipids, and also sets up a novel strategy of rationally modulating chiral and emissive properties of supramolecular materials, i.e., tunable CPL materials, by exploitation of the tail dissymmetry.

Graphical abstract: Dissymmetrical tails-regulated helical nanoarchitectonics of amphiphilic ornithines: nanotubes, bundles and twists

Supplementary files

Article information

Article type
Paper
Submitted
15 Huk 2021
Accepted
21 N’w 2021
First published
22 N’w 2021

Nanoscale, 2022,14, 1001-1007

Dissymmetrical tails-regulated helical nanoarchitectonics of amphiphilic ornithines: nanotubes, bundles and twists

H. Wang, L. Xu, X. Zhu, C. Xue, L. Zhang and M. Liu, Nanoscale, 2022, 14, 1001 DOI: 10.1039/D1NR07538A

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