Guest recognition of a tetrapyridinohemicarcerand through hydrogen bonding and constrictive binding interactions

Tetrapyridinohemicarcerand 2 having four hydrogen-bonding acceptors of inward-directing pyridyl units was synthesized and their binding properties for a variety of organic guest molecules have been investigated. Tetrapyridinohemicarcerand 2 formed kinetically stable complexes with various sulfonic acids via intermolecular –SO3H–pyridyl hydrogen bonding and constrictive binding interactions in C2D2Cl4 at 25 °C. But carboxylic acids or alcohols cannot be a stable guest at the same conditions. Tetrapyridinohemicarcerand 2 also binds various disubstituted benzenes. Especially 1,4-diiodobenzene forms stable hemicarceplex 1,4-diiodobenzene@2, which seems to be stabilized by constrictive binding as well as by –C–H⋯I interactions between dioxymethylene of 2 and iodo group of guest.