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Synthesis and Molecular Recognition of Water‐Soluble S 6 ‐Corona[3]arene[3]pyridazines
Author(s) -
Guo QingHui,
Zhao Liang,
Wang MeiXiang
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201503179
Subject(s) - chemistry , supramolecular chemistry , nucleophilic aromatic substitution , tetrazine , nucleophilic substitution , combinatorial chemistry , molecule , medicinal chemistry , organic chemistry
We report the efficient and scalable synthesis and molecular‐recognition properties of novel and water‐soluble S 6 ‐corona[3]arene[3]pyridazines. The synthesis comprises a one‐pot nucleophilic aromatic substitution reaction between diesters of 2,5‐dimercaptoterephthalate and 3,6‐dichlorotetrazine followed by the inverse electron‐demand Diels–Alder reaction of the tetrazine moieties with an enamine and exhaustive saponification of esters. The resulting S 6 ‐corona[3]arene[3]pyridazines, which adopt a 1,3,5‐alternate conformation in the crystalline state, are able to selectively form stable 1:1 complexes with dicationic guest species in water with association constants ranging from (1.10±0.06)×10 3 M −1 to (1.18±0.06)×10 5 M −1 . The easy availability, large cavity size, strong and selective binding power render the water‐soluble S 6 ‐corona[3]arene[3]pyridazines useful macrocyclic hosts in various disciplines of supramolecular chemistry.