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Citation: SONG Xiumei, FENG Zongcai, CHEN Jianqiao, WANG Zhaoyang, FENG Cuijuan, LU Yangli. Synthesis,Crystal Structure and Isomerization Property of 3',5'-Dibromo-3-methoxy-4-hydroxyazobenzene[J]. Chinese Journal of Applied Chemistry, ;2014, 31(11): 1273-1279. doi: 10.3724/SP.J.1095.2014.40001 shu

Synthesis,Crystal Structure and Isomerization Property of 3',5'-Dibromo-3-methoxy-4-hydroxyazobenzene

1.
a Development Center for New Materials Engineering & Technology in Universities of Guangdong, Industrial Technology Institute, Zhanjiang Normal College, Zhanjiang 524048, China;
2.
b School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China;
3.
c Faculty of Science, Shantou Polytechnic, Shantou 515078, China

Corresponding author: FENG Zongcai,
Received Date: 2 January 2014
Available Online: 11 March 2014
Fund Project: 广东省自然科学基金(S2011010001544) (S2011010001544)广东省高等学校高层次人才基金(批准号粤财教[2011]431号) (批准号粤财教[2011]431号)高分子材料工程国家重点实验室(四川大学)开放课题基金(KF201208)资助项目 (四川大学)开放课题基金(KF201208)

Starting from 4-amino nitrobenzene,3',5'-dibromo-3-methoxy-4-hydroxyazobenzene(6) was synthesized via sequential reactions of dibromination,diazotization deamination,nitro-reduction and diazo coupling.Polymethyl methacrylate(PMMA) films containing azobenzene 6 were obtained by a physical doping process.The structure of the title compound was characterized by elemental analysis,FT-IR,MS(ESI),¹H NMR,¹³C NMR,MS,especially by the X-ray single crystal diffraction.The crystal crystallizes in the monoclinic space group C2/c,with a=1.6182(3) nm,b=0.81847(16) nm,c=2.1945(4) nm,β=102.819(2)°,V=2.8342(10) nm³,Z=8,D_c=1.809 g/cm³,μ=5.719 mm^-1,F(000)=1504,R₁=0.0366 and ωR₂=0.0764.The title compound exists in the trans-form.The intermolecular hydrogen bonds and π-π stacking between benzene rings contributes to one-dimensional infinite chain structure along b axis.By UV-Vis spectroscopy method,the reaction rate constants for trans-cis photoisomerization and cis-trans thermal back-isomerization are at the range of 10^-1~10^-2min^-1.
- dibromo-methoxy-hydroxyazobenzene,
- crystal structure,
- trans-cis photoisomerization,
- thermal backisomerization,
- rate constant
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