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Molecular Waterwheel (Noria) from a Simple Condensation of Resorcinol and an Alkanedial
Author(s) -
Kudo Hiroto,
Hayashi Rieko,
Mitani Kouji,
Yokozawa Tsutomu,
Kasuga Noriko C.,
Nishikubo Tadatomi
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200603013
Subject(s) - surprise , resorcinol , oligomer , condensation , chemistry , yield (engineering) , organic chemistry , materials science , physics , sociology , thermodynamics , metallurgy , communication
A wheel surprise : Reaction of resorcinol and 1,5‐pentanedial in ethanol at 80 °C for 48 h in the presence of HCl surprisingly afforded a soluble cyclic oligomer in high yield (83 %) under thermodynamic control. Single‐crystal X‐ray analysis revealed a waterwheel‐like structure with a large hydrophobic hole through the center (see picture). A carboxylic ester derivative of the compound was shown to be highly selective for Rb + ions.