Self-Assembly of Ureido-Pyrimidinone Dimers into One-Dimensional Stacks by Lateral Hydrogen Bonding

Marko M.L. Nieuwenhuizen, Tom F.A. de Greef, Rob L.J. van der Bruggen, Jos M.J. Paulusse, Wilco P.J. Appel, Maarten M.J. Smulders, Rint P. Sijbesma, E.W. Meijer

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Ureido-pyrimidinone (UPy) dimers substituted with an additional urea functionality self-assemble into one-dimensional stacks in various solvents through lateral non-covalent interactions. 1H NMR and DOSY studies in CDCl3 suggest the formation of short stacks (<10), whereas temperature-dependent circular dichroism (CD) studies on chiral UPy dimers in heptane show the formation of much larger helical stacks. Analysis of the concentration-dependent evolution of chemical shift in CDCl3 and the temperature-dependent CD effect in heptane suggest that this self-assembly process follows an isodesmic pathway in both solvents. The length of the aggregates is influenced by substituents attached to the urea functionality. In sharp contrast, UPy dimers carrying an additional urethane group do not self-assemble into ordered stacks, as is evident from the absence of a CD effect in heptane and the concentration-independent chemical shift of the alkylidene proton of the pyrimidinone ring in CDCl3.
Original languageEnglish
Pages (from-to)1601-1612
Number of pages12
JournalChemistry : a European journal
Issue number5
Publication statusPublished - 2010
Externally publishedYes


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