Both authors contributed equally to this work.
Self-Assembled Pentamers and Hexamers Linked through Quadruple-Hydrogen-Bonded 2-Ureido-4[1H]-Pyrimidinones
Article first published online: 15 JUN 2005
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chemistry - A European Journal
Volume 11, Issue 16, pages 4602–4608, August 5, 2005
How to Cite
Keizer, H. M., González, J. J., Segura, M., Prados, P., Sijbesma, R. P., Meijer, E. W. and de Mendoza, J. (2005), Self-Assembled Pentamers and Hexamers Linked through Quadruple-Hydrogen-Bonded 2-Ureido-4[1H]-Pyrimidinones. Chem. Eur. J., 11: 4602–4608. doi: 10.1002/chem.200500329
- Issue published online: 25 JUL 2005
- Article first published online: 15 JUN 2005
- Manuscript Received: 23 MAR 2005
- gel permeation chromatography;
- hydrogen bonds;
The preorganization of bifunctional 2-ureido-4-pyrimidinones mediated by either 1,3-substituted adamantane or meta-substituted phenylene ring linkers leads to the preferred formation of stable pentameric (1)5 and hexameric (2)6 assemblies, respectively. Despite the high binding constant of the 2-ureido-4-pyrimidinone dimers and the highly preorganized structure of the monomer, the predominant formation of cycles (1)5 and (2)6 in solution occurs only within a specific concentration range.