摘要
以4-羧基-4'-羟基偶氮苯(CH-Azo)为偶氮苯化合物母体,经溴代烷取代、水解反应,再与S(-)-2-甲基-1-丁醇发生酯化反应,制备得到含溴代烷氧基反应性基团的手性偶氮苯化合物——4-(羧酸-2-甲基丁酯基)-4'-(1-溴丁氧基)偶氮苯(CMB-Azo).利用红外光谱(FT-IR)、核磁共振氢谱(1H-NMR)对其结构进行表征.通过紫外、可见光交替照射观察CMB-Azo和4-(羧酸-1-溴丁酯基)-4'-(1-溴丁氧基)偶氮苯(CBB-Azo)在甲醇溶液中的紫外可见吸收光谱变化.结果表明:在355 nm紫外光和455 nm可见光交替照射下,CMB-Azo和CBB-Azo均发生由反式到顺式和由顺式到反式的光异构化反应.由于手性碳原子的引入,顺式的CMB-Azo仅60%恢复到原来的反式结构.
A novel azobenzene compound containing bromobutoxy group and chiral carbon,4-（2-methyl butylcarboxylate）-4′-（1-bromobutoxy） azobenzene（CMB-Azo） was synthesized by subsequent reactions of substitution,hydrolysis and esterification.The structure of CMB-Azo was characterized by FT-IR and 1H-NMR.The Changes in UV-Vis spectra of CMB-Azo and 4-（1-bromobutyl carboxylate）-4′-（1-bromobutoxy） azobenzene（CBB-Azo） irradiated by the light were detected.The results showed that CMB-Azo and CBB-Azo in MeOH could undergo trans→cis isomerization irradiated with 355 nm UV-light,and cis→trans isomerization irradiated subsequently with 445 nm visible light.Compared with that of CBB-Azo,the photoisomerization of CMB-Azo changed slowly due to the introduction of chiral carbon.
出处
《沈阳化工大学学报》
CAS
2012年第3期224-229,269,共7页
Journal of Shenyang University of Chemical Technology
基金
辽宁省教育厅高等学校科研项目(20060681)
关键词
偶氮苯
手性碳
溴丁氧基
光异构化
azobenzene chiral carbon bromobutoxy group photoisomerization
