上缘 1,3-交替四氧杂杯[2]芳烃[2]三嗪氮杂冠醚的合成、结构及对氟阴离子响应时的空腔变化
Synthesis and structure of upper-rim 1,3-alternate tetraoxacalix[2]arene[2]triazine azacrowns and change of cavity in response to fluoride anion.
作者信息
Hou Bao-Yong, Wang De-Xian, Yang Hai-Bo, Zheng Qi-Yu, Wang Mei-Xiang
机构信息
Beijing National Laboratory for Molecular Sciences, Laboratory of Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100080, China.
出版信息
J Org Chem. 2007 Jul 6;72(14):5218-26. doi: 10.1021/jo0706168. Epub 2007 Jun 5.
The upper-rim 1,3-alternate tetraoxacalix[2]arene[2]triazine azacrowns were constructed effectively by macrocyclic condensation reaction of diamines with dichlorinated tetraoxacalix[2]arene[2]triazine intermediates that were synthesized from the stepwise fragment coupling reactions of 3,5-dihydroxybenzoic acid esters with cyanuric chlorides. Because of the formation of conjugation of amino groups with triazine rings, tetraoxacalix[2]arene[2]triazine azacrowns existed in a mixture of syn- and anti-isomeric forms. Both fluorescence titration and 1H NMR spectroscopic study showed that tetraoxacalix[2]arene[2]triazine azacrowns interacted with fluoride anion, leading to cavity changes of the host molecules.
通过二胺与二氯代四氧杂杯[2]芳烃[2]三嗪中间体的大环缩合反应，有效地构建了上缘为1,3-交替结构的四氧杂杯[2]芳烃[2]三嗪氮杂冠醚，其中二氯代四氧杂杯[2]芳烃[2]三嗪中间体是由3,5-二羟基苯甲酸酯与三聚氯氰的逐步片段偶联反应合成的。由于氨基与三嗪环形成共轭，四氧杂杯[2]芳烃[2]三嗪氮杂冠醚以顺式和反式异构体形式的混合物存在。荧光滴定和1H NMR光谱研究均表明，四氧杂杯[2]芳烃[2]三嗪氮杂冠醚与氟离子相互作用，导致主体分子的空腔发生变化。
Zotero 插件