Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 9, Issue 16, Pages 3904-3908Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200204555
Keywords
clays; intercalations; macrocycles; supramolecular chemistry; template synthesis
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A new approach for the synthesis of amide macrocycles, based on the use of organo-clay derivatives as controlling template, is proposed as an alternative to the rotaxane method. Dications of p-xylylene diamine inserted in the clay interlayer space act as molding pillars around which neutral diamine molecules are erected via hydrogen bonding and pi - pi interactions to form supramolecular arrays. Condensation of diamines in the supramolecular arrays with diacetyl dichlorides yields various tetramide macrocycles in good yields. Shape, aromaticity and dimensions of the reactants are factors affecting the condensation reaction.
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