Citation: Cheng-Yan Wu, Yi-Nan Gao, Zi-Han Zhang, Rui Liu, Quan Tang, Zhong-Lin Lu. Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages[J]. Chinese Chemical Letters, ;2024, 35(11): 109649. doi: 10.1016/j.cclet.2024.109649 shu

Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages

Cheng-Yan Wu ^{a, b} ,
Yi-Nan Gao ^a ,
Zi-Han Zhang ^a ,
Rui Liu ^a ,
Quan Tang ^{a, *,} ,
Zhong-Lin Lu ^{a, *,}

a.
College of Chemistry, Beijing Normal University, Beijing 100875, China
b.
College of Chemistry and Materials Engineering, Bohai University, Jinzhou 121013, China

tangquan@bnu.edu.cn

luzl@bnu.edu.cn

Received Date: 4 December 2023
Revised Date: 19 January 2024
Accepted Date: 4 February 2024
Available Online: 13 February 2024

Figures(6)

Constructing more stable self-assembled organic nanotubes has been one of the focuses of scientists in recent decades. Hexakis(m-phenylene ethynylene) (m-PE) benzene macrocycles can form stable tubular self-assemblies in nonpolar or weakly polar solvents through the π-π interaction of the main skeleton and the hydrogen bonding of the side chain amide. We covalently linked two macrocyclic units at the para position of the macrocycles using two oligo(β-alanine) linkers through an efficient synthetic route. UV–visible spectroscopy, fluorescence spectroscopy, and circular dichroism spectroscopy were employed to demonstrate that the incorporation of two peptide chains significantly enhances the stability of the self-assemblies. Meanwhile, the average open time of the ion channel formed by the macrocyclic dimer in the lipid bilayer was significantly better than that of the ion channel formed by a single macrocycle. This study shows that this strategy effectively improves the efficiency of self-assembly and the stability of its formed self-assemblies, providing a feasible strategy for constructing organic self-assembled nanotubes in highly polar solvents.
- Macrocyclic compounds,
- Supramolecular assembly,
- Ion transportation,
- Synthetic ion channels,
- Molecular nanotubes
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