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

doi:10.19894/j.issn.1000-0518.210356

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

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)

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Abstract

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 （Azo^2-） 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:

O641.3

Meng-Wei LI, Hong-Yan WANG, Ying-Ying WANG, Xiao-Ying KANG, Mei-Fang LIU, Yu-Lan CHEN. Supramolecular Self⁃Assembly of Azobenzene⁃4，4'⁃dicarboxylic Acid Derivatives in Water[J]. Chinese Journal of Applied Chemistry, 2021, 38(10): 1362-1370.

Figures/Tables 9

Fig.1 （A） Hydrogen bonding interactions between amidinium cations and carboxylate anions. （B） Structure of the supermolecular assembly TPM?Azo

Fig.2 Synthetic routes of Azo?2COONa， Azo?2TBA and TPM?4Cl

Fig.3 Photograph of needle-like TPM?Azo crystals taken under an optical microscope

Fig.4 FT-IR spectra of （A） Azo?2TBA， TPM?4Cl and the corresponding TPM?Azo and （B） Azo?2COONa， TPM?4Cl and the corresponding TPM?Azo

Fig.5 1H NMR spectrum of the acid-digested TPM?Azo （400 MHz， 298 K， DMSO-d6 containing a drop of conc. DCl（aq）， peak marked * corresponds to water）

Fig.6 （A） TGA and （B） DSC curves of TPM-Azo

Fig.7 Photographs of TPM?Azo crystals after the addition of HCl（aq） and NaOH（aq） taken under an optical microscope

Fig.8 UV-Vis absorption spectra of the aqueous solutions of （a） Azo?2TBA and （b） Azo?2COONa （2.0×105 mol/L） before and after the 365 nm UV irradiation for 8 min

Fig.9 Photographs of TPM?Azo crystals upon 365 nm UV irradiation taken under an optical microscope

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

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