Deng Caiming, Abdurehman Samat, Liu Lang, Wu Dongling, Jia Dianzeng, Zhou Rong
Key Laboratory of Material and Technology for Clean Energy, Ministry of Education, Institute of Applied Chemistry, Xinjiang University, Urumqi 830046, Xinjiang, China.
Key Laboratory of Material and Technology for Clean Energy, Ministry of Education, Institute of Applied Chemistry, Xinjiang University, Urumqi 830046, Xinjiang, China; State Key Laboratory on Integrated Optoelectronics, College of Electronic Science and Engineering, Jilin University, Changchun 130012, China.
Spectrochim Acta A Mol Biomol Spectrosc. 2015 Sep 5;148:318-23. doi: 10.1016/j.saa.2015.04.001. Epub 2015 Apr 9.
Through the design of molecules and the modification of structures, ten novel pyrazolone derivatives containing 3-cyanobenzal have been synthesized. They are 1-phenyl-3-methyl-4-(3-cyanobenzal)-5-hydroxypyrazole thiosemicarbazone (1)/4-methyl-3-thiosemicarbazone (2)/4-ethyl-3-thiosemicarbazone (3)/4-phenyl-3-thiosemicarbazone (4)/4-phenylsemicarbazone (5) and 1,3-diphenyl-4-(3-cyanobenzal)-5-hydroxypyrazole thiosemicarbazone (6)/4-methyl-3-thiosemicarbazone (7)/4-ethyl-3-thiosemicarbazone (8)/4-phenyl-3-thiosemicarbazone (9)/4-phenylsemicarbazone (10), in which seven compounds (1, 2, 3, 6, 7, 8 and 10) have photoisomerization behaviors. Their structures, photoisomerization properties, and first-order kinetics were investigated. The results show that the compounds 2, 3, 7 and 8 exhibit irreversible photoisomerization behaviors, the other three compounds have reversible photoisomerization behaviors under 365nm light irradiation and heat. But only 1,3-diphenyl-4-(3-cyanobenzal)-5-hydroxypyrazole 4-phenylsemicarbazone (10) exhibits good photochromic properties and fatigue resistance. Moreover, effects of various temperatures on the thermal bleaching reaction for 10 and substituent groups on the photochromic phenomenon are discussed.
通过分子设计和结构修饰，合成了10种含3-氰基亚苄基的新型吡唑啉酮衍生物。它们分别是1-苯基-3-甲基-4-(3-氰基亚苄基)-5-羟基吡唑硫代半卡巴腙(1)/4-甲基-3-硫代半卡巴腙(2)/4-乙基-3-硫代半卡巴腙(3)/4-苯基-3-硫代半卡巴腙(4)/4-苯基半卡巴腙(5)以及1,3-二苯基-4-(3-氰基亚苄基)-5-羟基吡唑硫代半卡巴腙(6)/4-甲基-3-硫代半卡巴腙(7)/4-乙基-3-硫代半卡巴腙(8)/4-苯基-3-硫代半卡巴腙(9)/4-苯基半卡巴腙(10)，其中7种化合物(1、2、3、6、7、8和10)具有光异构化行为。对它们的结构、光异构化性质和一级动力学进行了研究。结果表明，化合物2、3、7和8表现出不可逆的光异构化行为，其他三种化合物在365nm光照和加热条件下具有可逆的光异构化行为。但只有1,3-二苯基-4-(3-氰基亚苄基)-5-羟基吡唑4-苯基半卡巴腙(10)表现出良好的光致变色性能和抗疲劳性。此外，还讨论了不同温度对10的热漂白反应的影响以及取代基对光致变色现象的影响。
