对叔丁基杯[4]芳烃-1,3-二取代邻菲罗啉衍生物的合成及对Ag^+的识别作用

1,3-Disubstituted p-tert-Butylcalix[4]arene Derivatives Bearing Phenanthroline Moieties: Synthesis and Selective Recognition of Silver Ion

以对叔丁基杯[4]芳烃为母体,首先通过两步烃基化反应合成出烷基桥联的氧代芳醛化合物,接着与1,10-邻菲罗啉-5,6-二酮反应,得到了邻菲罗啉为功能基团的杯芳烃衍生物.化合物结构均用IR,NMR和ESI-HRMS进行了表征.利用紫外可见吸收光谱,详细研究了配体3c对金属离子的识别性能.结果发现:其对Ag+显示出优异的选择性,并可以实现对Ag+的"裸眼"识别,检测限达到5×10-6mol/L.

p-tert-Butylcalix[4]arene-l,3-dialdehydes were firstly obtained by two step alkylations ofp-tert-butylcalix[4]arene with alkylene dihalide and hydroxyl-substituted benzaldehydes. Then p-tert-butylcalix[n]arene 1,3-disubstituted phenanthrolines were successfully prepared by condensation of active calixarene dialdehydes with 1,10-phenanthroline-5,6-dione. The structures of the prepared hoters were characterized with IR, NMR, and HRMS techniques. The recogination of calixarene 1,3-disubstituted phenanthroline for metal ions was studied with UV-Vis spectroscopy. A great affinity for Ag＋ ions that can be clearly detected by naked eye was obtained.