沈阳化工大学学报
瀋暘化工大學學報
침양화공대학학보
JOURNAL OF SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
2011年
4期
310-315,325
,共7页
偶氮苯%手性%照射%光异构化
偶氮苯%手性%照射%光異構化
우담분%수성%조사%광이구화
azobenzene%chirality%irradiation%photoisomerization
以对氨基苯甲酸为原料,经重氮偶合、取代和酯化等一系列反应,合成一种新型含手性碳的偶氮苯化合物——4-(羧酸-2-甲基丁酯酯基)-(4'-辛氧基)偶氮苯(MBCO-Azo).利用红外光谱(FT-IR)和核磁共振氢谱(1H-NMR)对其结构进行了鉴定.通过紫外可见吸收光谱(UV-Vis)研究MBCO-Azo在甲醇溶液中的光异构化反应.结果表明:在360 nm紫外光照射下,MBCO-Azo发生由反式到顺式异构化反应,随后在440 nm可见光照射下发生由顺式到反式异构化反应.在光异构化中MBCO-Azo最大吸收波长变化较宽,可达到24 nm.由于手性单元的引入,MBCO-Azo由反式到顺式的光异构化速率略大于4-(羧基)-(4'-辛氧基)偶氮苯(CO-Azo),而顺式到反式的回复速率则略小.
以對氨基苯甲痠為原料,經重氮偶閤、取代和酯化等一繫列反應,閤成一種新型含手性碳的偶氮苯化閤物——4-(羧痠-2-甲基丁酯酯基)-(4'-辛氧基)偶氮苯(MBCO-Azo).利用紅外光譜(FT-IR)和覈磁共振氫譜(1H-NMR)對其結構進行瞭鑒定.通過紫外可見吸收光譜(UV-Vis)研究MBCO-Azo在甲醇溶液中的光異構化反應.結果錶明:在360 nm紫外光照射下,MBCO-Azo髮生由反式到順式異構化反應,隨後在440 nm可見光照射下髮生由順式到反式異構化反應.在光異構化中MBCO-Azo最大吸收波長變化較寬,可達到24 nm.由于手性單元的引入,MBCO-Azo由反式到順式的光異構化速率略大于4-(羧基)-(4'-辛氧基)偶氮苯(CO-Azo),而順式到反式的迴複速率則略小.
이대안기분갑산위원료,경중담우합、취대화지화등일계렬반응,합성일충신형함수성탄적우담분화합물——4-(최산-2-갑기정지지기)-(4'-신양기)우담분(MBCO-Azo).이용홍외광보(FT-IR)화핵자공진경보(1H-NMR)대기결구진행료감정.통과자외가견흡수광보(UV-Vis)연구MBCO-Azo재갑순용액중적광이구화반응.결과표명:재360 nm자외광조사하,MBCO-Azo발생유반식도순식이구화반응,수후재440 nm가견광조사하발생유순식도반식이구화반응.재광이구화중MBCO-Azo최대흡수파장변화교관,가체도24 nm.유우수성단원적인입,MBCO-Azo유반식도순식적광이구화속솔략대우4-(최기)-(4'-신양기)우담분(CO-Azo),이순식도반식적회복속솔칙략소.
A novel azobenzene compound containing chiral carbon,4-(2-methyl butylcarboxylate)-(4′-octyloxy)azobenzene(MBCO-Azo)was synthesized by diazo coupling,substitution and esterification reaction.The structures of compounds were characterized by FT-IR and 1H-NMR.The photoisomerization of MBCO-Azo was investigated using UV-Vis spectroscopy.The results indicate that MBCO-Azo in MeOH can undergo trans→cis isomerization irradiated with 360 nm UV-light,and cis→trans isomerization irradiated subsequently with 440 nm visible light.The change of the maximum absorption wavelength of MBCO-Azo became widely.The ratio of trans→cis isomerization of MBCO-Azo was slightly faster than that of 4-(carboxy)-(4′-octyloxy)azobenzene(CO-Azo),while the ratio of cis→trans isomerization of MBCO-Azo was slight slower than that of CO-Azo due to the introduction of chiral carbon.