含溴丁氧基的手性偶氮苯化合物的合成及其光异构化  

Synthesis and Photoisomerization of Azobenzene Compound Containing Bromobutoxy Group and Chiral Carbon

作　　者：赵常礼[1] 何延胜[1] 刘坤[1] 

机构地区：[1]沈阳化工大学材料科学与工程学院,辽宁沈阳110142

出　　处：《沈阳化工大学学报》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)

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.

关 键 词：偶氮苯 手性碳 溴丁氧基 光异构化 

分 类 号：O623.626[理学—有机化学]