Synthesis of Butadiynyl-Strapped Corona[6]arenes and Their Selective Anion Binding Properties
Synthesis of Butadiynyl-Strapped Corona[6]arenes and Their Selective Anion Binding Properties
复制标题
丁二炔基环[6]芳烃的合成及其选择性阴离子结合特性
DOI：
10.1021/acs.joc.9b03017
复制
发表时间：
2020-02-21
影响因子：
3.6
通讯作者：
Wang, Mei-Xiang
中科院分区：
文献类型：
--
作者：
Gu, Meng-Di;Lu, Yao;Wang, Mei-Xiang
通过O-6-冠[6]芳烃的分子内氧化同位偶联，直接合成了一系列丁二炔键合的O-6-冠[6]芳烃，其中至少含有两个N-丙叉基邻苯二甲酰亚胺链段。3，6-二氯四嗪与N-丙叉基-3，6-二羟基邻苯二甲酰亚胺和另一种摩尔比约为3：2：1.3-1.5的1，4-二羟基苯衍生物以一锅法合成了单环反应物。所合成的丁二苯冠醚[3]芳烃[3]四氮杂环作为高选择性缺电子大环主体与硫氰酸盐形成1：1的络合物，缔合常数(K-a)达1390M-1。阴离子-pi的非共价相互作用提供了主客体络合的驱动力。
A number of butadiynylene-strapped O-6-corona[6]arenes were synthesized straightforwardly through intramolecular oxidative homocoupling of O-6-corona[6]arenes, which contained at least two N-propargyl-phthalimide segments. The monomacrocyclic reactants were prepared from the reaction between 3,6-dichlorotetrazine and N-propargyl-3,6-dihydroxyphthalimide and another 1,4-dihydroxybenzene derivative with roughly a 3:2:1.3-1.5 ratio in a one-pot reaction manner. The synthesized butadiynylene-strapped corona[3]arene[3]tetrazines acted as highly selective electron-deficient macrocyclic hosts to form 1:1 complexes with thiocyanate in solution, and the association constant (K-a) was up to 1390 M-1. The anion-pi noncovalent interactions provided the driving force for host-guest complexation.