Synthesis and Molecular Recognition of Water‐Soluble S6‐Corona[3]arene[3]pyridazines

E-ISSN： 1521-3773|54|29|8386-8389

ISSN： 1433-7851

Source： ANGEWANDTE CHEMIE INTERNATIONAL EDITION, Vol.54, Iss.29, 2015-07, pp. : 8386-8389

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Abstract

AbstractWe report the efficient and scalable synthesis and molecular‐recognition properties of novel and water‐soluble S6‐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 S6‐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)×103 M−1 to (1.18±0.06)×105 M−1. The easy availability, large cavity size, strong and selective binding power render the water‐soluble S6‐corona[3]arene[3]pyridazines useful macrocyclic hosts in various disciplines of supramolecular chemistry.