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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201503179
Subject(s) - chemistry , supramolecular chemistry , nucleophilic aromatic substitution , tetrazine , molecular recognition , catenane , nucleophile , nucleophilic substitution , combinatorial chemistry , molecule , medicinal chemistry , organic chemistry , catalysis
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.