2,5-二苯基-1,3,4-噻二唑衍生物的一锅法合成及性质研究  

One pot synthesis and charateristic of 2,5-diphenyl-1,3,4-thiadiazole

作　　者：彭雄伟[1] 谭晓平[1] 张瑞林 程晓红[1] 

机构地区：[1]教育部自然资源药物化学重点实验室云南大学化学科学与工程学院,云南昆明650091

出　　处：《云南大学学报（自然科学版）》2016年第4期632-637,共6页Journal of Yunnan University(Natural Sciences Edition)

基　　金：国家自然科学基金(21274119;21364017);云南省自然科学基金重点项目(2013FA007);云南省教育厅科研基金重大项目(ZD2015001)

摘　　要：从易得原料苯甲酰氯和苯甲酰肼出发,一锅法完成了3个2,5-二苯基-1,3,4-噻二唑衍生物的高效合成.研究发现,当原料苯甲酰肼中苯环上取代基为CN、NO_2、OCH_3时,预期产物用该合成方法能获得较好的产率;当取代基为碘时,由于产物复杂,无法获得预期产物.紫外荧光光谱测试表明,所合成的2,5-二苯基-1,3,4噻二唑衍生物在蓝光材料和有机半导体材料中具有潜在的应用前景.密度泛函理论(DFT)计算结果显示该类化合物具有共平面结构,末端吸电子取代基能引起ICT(分子内电荷转移)效应.Starting form readily available materials （benzoyl chloride and benzoyl hydrazine） via one-pot way,three 2,5- bisphenyl -1,3,4-thiadiazole derivatives were synthesized.When the benzoyl hydrazines have the substituents as R =-NO2,-OCH3,-CN respectively , expected 2,5- diphenyl -1,3,4- thiadiazole products with good yields can be obtained, when the benzoyl hydrazine has the substituent as R--I , no expected product can be separated.UV and fluorescence spectra indicated that these materials could be used as potential blue emi- ting and organic semiconductor materials.Theoretical calculations based on density functional theory（DFT） with the Gaussian 03W program package at B3LYP/（6-31G,d） level indicated that these compounds have coconju- gated configurations and ICT effects induced by terminal electro withdrawing groups.

关 键 词：1 3 4-噻二唑 一锅法 有机合成 

分 类 号：O626.25[理学—有机化学]