Hierarchical self-assembly of a bow-shaped molecule bearing self-complementary hydrogen bonding sites into extended supramolecular assemblies |
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Authors: | Ikeda Masato Nobori Tadahito Schmutz Marc Lehn Jean-Marie |
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Affiliation: | Laboratoire de Chimie Supramoléculaire, ISIS, Université Louis Pasteur, 8, allée Gaspard Monge, BP 70028, 67083 Strasbourg Cedex, France. |
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Abstract: | The bow-shaped molecule 1 bearing a self-complementary DAAD-ADDA (D=donor A=acceptor) hydrogen-bonding array generates, in hydrocarbon solvents, highly ordered supramolecular sheet aggregates that subsequently give rise to gels by formation of an entangled network. The process of hierarchical self-assembly of compound 1 was investigated by the concentration and temperature dependence of UV-visible and (1)H NMR spectra, fluorescence spectra, and electron microscopy data. The temperature dependence of the UV-visible spectra indicates a highly cooperative process for the self-assembly of compound 1 in decaline. The electron micrograph of the decaline solution of compound 1 (1.0 mM) revealed supramolecular sheet aggregates forming an entangled network. The selected area electronic diffraction patterns of the supramolecular sheet aggregates were typical for single crystals, indicative of a highly ordered assembly. The results exemplify the generation, by hierarchical self-assembly, of highly organized supramolecular materials presenting novel collective properties at each level of organization. |
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Keywords: | hydrogen bonds molecular recognition self‐assembly supramolecular chemistry supramolecular polymers |
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