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Synthesis of O 6 ‐Corona[3]arene[3]pyridazines and Their Molecular Recognition Property in Organic and Aqueous Media
Author(s) -
Lu Yao,
Liang DongDong,
Fu ZhanDa,
Guo QingHui,
Wang MeiXiang
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201800131
Subject(s) - chemistry , pyridazine , aqueous solution , tetrazine , rotaxane , polymer chemistry , medicinal chemistry , molecule , organic chemistry , supramolecular chemistry
O 6 ‐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 O 6 ‐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) × 10 1 to (2.53 ± 0.33) × 10 5 L·mol −1 . Water soluble O 6 ‐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) × 10 4 L·mol −1 . The pseudo‐rotaxane and inclusion structures of the host‐guest complexes were revealed by the X‐ray crystallography.