Novel macrocyclic compounds as building blocks in supramolecular chemistry
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Resorcinarenes and pyrogallolarenes have been widely used as building blocks for novel synthetic receptors and supramolecular self-assemblies. To explore new chemistry of these compounds, new substituted macrocyclic arenes were synthesized. Introduction of functionalities such as nitro, cyano, and amido groups into the resorcinarene molecule can significantly change the chemical properties of these macrocycles. The spectroscopic data and X-ray crystal structures of the new tetracyano resorcinarenes show that these compounds adopt a crown conformation and that all alkyl substituents are in the axial position. No hydrogen-bonded self-assembly is observed suggesting that the presence of a cyano group inhibits the formation of the hydrogen bonds between the macrocycles. The complex of silver(I) ion and tetracyano resorcinarene is a three dimensional polymer in which the silver center is coordinated by three cyano groups of the macrocycle and possesses an unusual trigonal planar geometry. No new tetranitro and tetraamido resorcinarenes were synthesized under the studied conditions.