Citation: SONG Xiumei, FENG Zongcai, WANG Zhaoyang, CHEN Xiaoling, LIANG Zhimei, LIANG Yanyu. Synthesis, Characterization and Photoisomerization Properties of Pseudostilbene Azobenzenes[J]. Chinese Journal of Applied Chemistry, ;2016, 33(4): 442-451. doi: 10.11944/j.issn.1000-0518.2016.04.150282 shu

Synthesis, Characterization and Photoisomerization Properties of Pseudostilbene Azobenzenes

1.
a Development Center for New Materials Engineering & Technology in Universities of Guangdong, Industrial Technology Research Institute, Lingnan Normal University, Zhanjiang, Guangdong 524048, China;
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b School of Chemistry and Chemical Engineering, Lingnan Normal University, Zhanjiang, Guangdong 524048, China;
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c School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China

Corresponding author: FENG Zongcai,
Received Date: 6 August 2015
Available Online: 19 November 2015
Fund Project:

A series of novel pseudostilbene azobenzenes was synthesized and their structures were characterized by FT-IR, NMR, MS(ESI) and elemental analysis. The photoisomerization properties and reversible cis/trans isomerization rate constants in solvent were measured via UV-Vis spectroscopy, as well as the fatigue resistance property in polymethyl methacrylate(PMMA) film was performed. The azobenzenes in ethyl acetate have the two bands of π-π^* and n-π^* inverted on the energy scale and π-π^* and n-π^* bands are practically superimposed. The isomerization rate constants range from 10^-1 to 10⁰ s^-1. The trans to cis isomerization rate constants depend on the dipole-dipole interactions and molecular steric hindrance, with the dipole-dipole interactions having larger impact on monobromo-azobenzenes than dibromo-azobenzenes, and a reverse impact from molecular steric hindrances. The faster trans to cis transformation corresponds to the slower cis to trans transformation. The azobenzene has a good fatigue resistance to some extent in PMMA film.
- pseudostilbene azobenzenes,
- azo coupling,
- photochromic,
- cis/trans isomerization,
- rate constant
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