单取代对叔丁基杯[6]芳烃Schiff碱的合成及对金属离子的识别性能  

Syntheses and recognition for metal ion of mono-substituted p-tert-butylcalix [6] arene Schiff bases

作　　者：李亮[1] 李浩克[1] 颜朝国[2] 

机构地区：[1]上海应用技术学院化学与环境工程学院,上海201418 [2]扬州大学化学化工学院,江苏扬州225002

出　　处：《化学试剂》2013年第10期883-886,932,共5页Chemical Reagents

基　　金：国家自然科学基金资助项目(20972132);上海高校青年教师培养资助计划项目(ZZyyy12006);上海应用技术学院引进人才基金资助项目(YJ-2012-10)

摘　　要：以对叔丁基杯[6]芳烃为母体单元超声震荡,在K2CO3/KI/CH3CN的体系中,与氯乙酸乙酯反应合成出单取代对叔丁基杯[6]芳烃氧代乙酸乙酯衍生物,与水合肼反应,得到单取代对叔丁基杯[6]芳烃酰肼衍生物,继续和水杨醛或2-羟基-1-萘醛反应,得到目标化合物,其结构用IR,1HNMR进行了表征。利用紫外可见吸收光谱,详细研究了化合物5,11,17,23,29,35-六叔丁基-37-[(水杨醛亚胺基酰胺基)甲氧基]-38,39,40,41,42-五羟基六叔丁基杯[6]对金属离子的识别性能。结果发现,其对Ni2+的识别效果最好,形成1∶1的配合物,键合常数为8.2×104L/mol。Mono-substituted p-tert-butylcalix [ 61 arene deriva- tives with different Schiff base groups were efficiently pre- pared in three steps. Firstly,p-tert-butylcalix[ 6 ] arene was ul- trasonic monoalkylation with ethyl a-chloroacetate in the sys- tem of K2COJKI/CH3CN to give mono-substituted ethoxy- carbonylmethoxy calix [ 6 ] arene derivatives, which was hydrazinolyzed to give mono-substituted calix[ 6 ] arene hydra- zide derivatives. Then by condensation of the latter with salicylaldehyde and 2-hydroxy-l-naphthaldehyde, a series of calixarene Schiff bases were obtained in moderate yields. The structures were confirmed by IR and 1HNMR. The complexing properties of Schiff bases 3a for transition metal ions were in- vestigated via UV spectroscopy. The results indicated that one of the title compounds showed an excellent affinity for Ni2＋ and formed 1 ： 1 stoichiometric complex, with the association constant of 8.2×10^4L/mol.

关 键 词：杯芳烃 SCHIFF碱 紫外吸收光谱 识别 

分 类 号：O625.1[理学—有机化学]