Journal ArticleDOI
Strong dimerization of ureidopyrimidones via quadruple hydrogen bonding
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TLDR
In this paper, a donor-donor-acceptor−acceptor −acceptor (DDAA) array of hydrogen bonding sites in the 4[1H]-pyrimidinone tautomer was used to preorganize the molecules for dimerization.Abstract:
6-Methyl-2-butylureidopyrimidone dimerizes via four hydrogen bonds in the solid state as well as in CHCl3 solution via a donor−donor−acceptor−acceptor (DDAA) array of hydrogen bonding sites in the 4[1H]-pyrimidinone tautomer. An intramolecular hydrogen bond from the pyrimidine NH group to the urea oxygen atom preorganizes the molecules for dimerization. The dimerization constant of the dimer in CHCl3 exceeds 106 M-1. In CHCl3 containing DMSO, the dimer is in equilibrium with the monomeric 6[1H]-pyrimidinone tautomer. In 6-phenyl-2-butylureidopyrimidone, the 4[1H]-pyrimidinone tautomer coexists with the pyrimidin-4-ol form, which dimerizes with similar high dimerization constants via four hydrogen bonds in a DADA array. The latter tautomer predominates in derivatives with electronegative 6-substituents, like 6-nitrophenyl- and 6-trifluoromethyl-2-butylureidopyrimidone. Due to its simple preparation and high dimerization constant, the ureidopyrimidone functionality is a useful building block for supramolecu...read more
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A field guide to foldamers.
TL;DR: I. Foldamer Research 3910 A. Backbones Utilizing Bipyridine Segments 3944 1.
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Stimuli-responsive supramolecular polymeric materials.
TL;DR: This critical review of recent developments in supramolecular polymeric materials is addressed, which can respond to appropriate external stimuli at the fundamental level due to the existence of noncovalent interactions of the building blocks.
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Self-healing polymeric materials
Ying Yang,Marek W. Urban +1 more
TL;DR: This review outlines the recent advances in the field of self-healing polymers, and the primary classes are the covalent bonding, supramolecular assemblies, ionic interactions, chemo-mechanical self- healing, and shape memory polymers.
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Noncovalent synthesis using hydrogen bonding
TL;DR: Noncovalent synthesis based on the reversible formation of multiple hydrogen bonds is described and the development of novel materials (nanotubes, liquid crystals, polymers, etc.) and principles that recently have emanated from this intriguing field of research are summarized.
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Binding Mechanisms in Supramolecular Complexes
TL;DR: The aim of this Review is to describe the crucial interaction mechanisms in context, and thus classify the entire subject of supramolecular chemistry.
References
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Journal ArticleDOI
Reversible Polymers Formed from Self-Complementary Monomers Using Quadruple Hydrogen Bonding
Rint P. Sijbesma,Felix Hugo Beijer,Felix Hugo Beijer,Luc Brunsveld,Luc Brunsveld,B. J. B. Folmer,B. J. B. Folmer,J. H. K. Ky Hirschberg,J. H. K. Ky Hirschberg,Ronald Frans Maria Lange,Ronald Frans Maria Lange,Jimmy K. L. Lowe,Jimmy K. L. Lowe,E. W. Meijer,E. W. Meijer +14 more
TL;DR: 2-ureido-4-pyrimidone that dimerize strongly in a self-complementary array of four cooperative hydrogen bonds were used as the associating end group in reversible self-assembling polymer systems.
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Self-assembling organic nanotubes based on a cyclic peptide architecture
TL;DR: The design, synthesis and characterization of a new class of organic nanotubes based on rationally designed cyclic polypeptides are reported, which may have possible applications in inclusion chemistry, catalysis, molecular electronics and molecular separation technology.
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