Synthesis and Properties of Symmetric Azobenzene Derivative†

doi:10.7503/cjcu20150839

Abstract

Abstract:

A new symmetric azobenzene compound(A) with triple alkoxy chain in each terminal was synthesized via Cu(Ⅰ)-catalyzed amino coupling reaction as the key step. The structure of this compound was identified with ¹H NMR, ¹³C NMR and elemental analysis. The property of compound A was investigated by UV-Vis spectroscopy and scanning electron microscopy(SEM). The results showed that compound A can form organolgels with different organic solvents, and the sol-gel transition could be observed under UV and visible light irradiation. The SEM images of xerogels of compound A showed the formation of three-dimensional networks composed of entangled fibrous aggregates. The gels were heating-, light- and mechan- responsive. The UV-Vis spectroscopy confirmed the photoresponsible behavior of compound A.

Key words: Azobenzene, Photoresponsible behavior, Gel

CLC Number:

O625.65

TrendMD:

YAN Chao, XIAO Yulong, DAI Heng, CHENG Xiaohong. Synthesis and Properties of Symmetric Azobenzene Derivative^†[J]. Chem. J. Chinese Universities, 2016, 37(3): 475.

Figures/Tables 5

Table 1 Gels prepared with compound A in different solvents*

Solvent	Form of compound A	Solvent	Form of compound A
Toluene	Solution	DMSO	Insolution
Cyclohexanone	Solution	Ethylacetate	Precipitation
n-Butanol	Gelation	n-Hexane	Precipitation
1,4-Dioxane	Gelation	V(Methanol)∶V(Dichloromethane)=1∶1	Gelation
Pyridine	Gelation	Cyclohexane	Precipitation
Acetone	Gelation	DMF	Insolution

Fig.1 Photographs of gels prepared with compound A in n-butanol

Fig.2 SEM images of xerogel formed by compound A in n-butanol(A) and in 1,4-dioxane(B)

Fig.3 Photoinduced reversible gel-sol transitions in n-butanol gel of compound A

Fig.4 UV-Vis spectra of compound A in CH2Cl2 under irradiation of UV-light(A) and visible light(B) Time/s: a—f. 5, 15, 60, 120, 300, 600.

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