Synfacts 2007(2): 0157-0157  
DOI: 10.1055/s-2006-955820
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Synthesis of A Molecular Waterwheel

Contributor(s): Timothy M. Swager, Wei Zhang
H. Kudo, R. Hayashi, K. Mitani, T. Yokozawa, N. C. Kasuga, T. Nishikubo*
Kanagawa University, Japan
Further Information

Publication History

Publication Date:
23 January 2007 (online)

Significance

A unique double-cyclic ladder-type oligomer (4) with a central hole, which resembles a waterwheel architecture, was synthesized in one step via the condensation reaction of resorcinol (1, difunctional unit) with 1,5-pentanedial (2, tetra­functional unit). Compound 4 was characterized by NMR spectroscopy, mass spectrometry as well as X-ray single crystal analysis. Mechanism studies by examining the size-exclusion chromatography (SEC) profiles of the obtained products over time revealed that compound 3 is the key intermediate on the reaction pathway leading to the final product formation. The ester derivative of 4 showed excellent selectivity for Rb+ ion, which was presumably enclosed in the central hole in the molecule.