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 resorcin[4]arene molecule can significantly change the chemical properties of these macrocycles. The spectroscopic data and X-ray crystal structures of the new tetracyano resorcin[4]arenes 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 resorcin[4]arene 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 resorcin[4]arenes were synthesized under the studied conditions.
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