Resorcinarene

In chemistry, a resorcinarene (also resorcarene or calix[4]resorcinarene) is a macrocycle, or a cyclic oligomer, based on the condensation of resorcinol (1,3-dihydroxybenzene) and an aldehyde. Resorcinarenes are a type of calixarene. Other types of resorcinarenes include the related pyrogallolarenes and octahydroxypyridines, derived from pyrogallol and 2,6-dihydroxypyridine, respectively.

Resorcinarenes interact with other molecules forming a host–guest complex.[1] Resorcinarenes and pyrogallolarenes self-assemble into larger supramolecular structures. Both in the crystalline state and in organic solvents, six resorcinarene molecules are known to form hexamers with an internal volume of around one cubic nanometer (nanocapsules) and shapes similar to the Archimedean solids.[2] Hydrogen bonds appear to hold the assembly together. A number of solvent or other molecules reside inside.[3] The resorcinarene is also the basic structural unit for other molecular recognition scaffolds, typically formed by bridging the phenolic oxygens with alkyl or aromatic spacers.[4] A number of molecular structures are based on this macrocycle, namely cavitands and carcerands.

  1. ^ Aoyama Y, Tanaka Y, Toi H, Ogoshi H (1988). "Polar host–guest interaction. Binding of nonionic polar compounds with a resorcinol-aldehyde cyclooligomer as a lipophilic polar host". Journal of the American Chemical Society. 110 (2): 634–635. Bibcode:1988JAChS.110..634A. doi:10.1021/ja00210a073.
  2. ^ Atwood JL, Barbour LJ, Jerga A (2002). "Organization of the interior of molecular capsules by hydrogen bonding". Proceedings of the National Academy of Sciences. 99 (8): 4837–4841. Bibcode:2002PNAS...99.4837A. doi:10.1073/pnas.082659799. PMC 122679. PMID 11943875.
  3. ^ Shivanyuk A, Rebek J (2001). "Reversible encapsulation by self-assembling resorcinarene subunits". Proceedings of the National Academy of Sciences. 98 (14): 7662–7665. Bibcode:2001PNAS...98.7662S. doi:10.1073/pnas.141226898. PMC 35398. PMID 11427733.
  4. ^ Jordan, J. H.; Gibb, B. C. (2017). "1.16 - Water-Soluble Cavitands☆". In Atwood, Jerry (ed.). Comprehensive Supramolecular Chemistry II. Elsevier. pp. 387–404. ISBN 9780128031995.
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