Chinese Journal of Applied Chemistry ›› 2021, Vol. 38 ›› Issue (10): 1362-1370.DOI: 10.19894/j.issn.1000-0518.210356

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Supramolecular Self⁃Assembly of Azobenzene⁃4,4'⁃dicarboxylic Acid Derivatives in Water

Meng-Wei LI1(), Hong-Yan WANG1, Ying-Ying WANG1, Xiao-Ying KANG1, Mei-Fang LIU2(), Yu-Lan CHEN1   

  1. 1Tianjin Key Laboratory of Molecular Optoelectronic Science,Institute of Molecular Plus,Tianjin University,Tianjin 300354,China
    2College of Chemistry-Chemical & Environmental Engineering,Weifang University,Weifang 261061,China
  • Received:2021-07-21 Accepted:2021-08-31 Published:2021-10-01 Online:2021-10-15
  • Contact: Meng-Wei LI,Mei-Fang LIU
  • About author:liumf@iccas.ac.cn; lmw@tju.edu.cn
  • Supported by:
    National Key Research and Development Program of China(2017YFA0204503);the National Natural Science Foundation of China(51903187);the China Postdoctoral Science Foundation(2020M670642)

Abstract:

Two azobenzene-based carboxylates (Azo-2TBA Azo-2COONa) and a tetrapenylmethane-containing tetra-amidinium (TPM-4Cl) were designed and synthesized. Both the two carboxylates could assemble with TPM-4Cl in aqueous media through hydrogen bonding and electrostatic interaction, resulting needle-like crystals with high stability and high aspect ratio. The supramolecular structures constituted of tetra-amidinium (TPM4+) and carboxylates (Azo2-) in a molar ratio of 1∶2 were confirmed by Fourier transform infrared(FT-IR) and nuclear magnetic resonance (NMR) analysis. Additionally, it was found that the self-assembly and disassembly of assemblies could be regulated by acid or base triggers. This work not only provides a simple, green and efficient approach to construct three-dimensional ordered supramolecular structures, but also facilitates their applications in selective encapsulation and release of guests, such as small molecule drugs.

Key words: Self-assembly, Azobenzene, Acid-response, Hydrogen bonding interactions

CLC Number: