Synthesis of O6‐Corona[3]arene[3]pyridazines and Their Molecular Recognition Property in Organic and Aqueous Media
Synthesis of O6‐Corona[3]arene[3]pyridazines and Their Molecular Recognition Property in Organic and Aqueous Media
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DOI：
10.1002/cjoc.201800131
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发表时间：
2018-07
影响因子：
5.4
通讯作者：
Yao-Bin Lu;Dong-Dong Liang-Dong;Zhan-Da Fu;Q. Guo;Mei-Xiang Wang
中科院分区：
文献类型：
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作者：
Yao-Bin Lu;Dong-Dong Liang-Dong;Zhan-Da Fu;Q. Guo;Mei-Xiang Wang
通过3，6-二氯四嗪与1，4-二苯醌衍生物的大环缩合反应，再与环戊酮衍生物的烯胺进行反电子需Diels-桤木反应，一锅法合成了O 6-冠[3]芳烃[3]哒嗪。将大环内的六个酯基转化为所有乙酸钠部分，得到水溶性O 6-冠[3]芳烃[3]哒嗪。在有机溶剂中，冠状大环主体与有机铵和二腈客体以1：1的化学计量比选择性地形成配合物，缔合常数为（2.96 ± 0.10）× 101 ~（2.53 ± 0.33）× 105 L·mol−1.水溶性O 6-冠[3]芳烃[3]哒嗪在水中也能与有机铵形成强络合物，其缔合常数可达（2.67 ± 0.21）× 104 L·mol−1。通过X射线晶体学分析，揭示了主客体配合物的赝轮烷结构和包合结构。
O6‐Corona[3]arene[3]pyridazines were synthesized from the one‐pot macrocyclic condensation reaction of 3,6‐dichlorotetrazine with 1,4‐dihydroquinone derivatives followed by the inverse electron demand Diels‐Alder reaction of the tetrazine rings with a cyclopentanone‐derived enamine. Conversion of six ester groups within macrocycle into all sodium acetate moieties afforded a water soluble O6‐corona[3]arene[3]pyridazine. The coronary macrocycle host formed complexes selectively with organic ammoniums and dinitrile guests in a 1: 1 stoichiometric ratio in organic solvents with association constants ranging from (2.96 ± 0.10) × 101to (2.53 ± 0.33) × 105L·mol−1. Water soluble O6‐corona[3]arene[3]pyridazine was also able to complex strongly with organic ammoniums in water to give an association constant up to (2.67 ± 0.21) × 104L·mol−1. The pseudo‐rotaxane and inclusion structures of the host‐guest complexes were revealed by the X‐ray crystallography.