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Hierarchical Self‐Assembly of a Bow‐Shaped Molecule Bearing Self‐Complementary Hydrogen Bonding Sites into Extended Supramolecular Assemblies
Author(s) -
Ikeda Masato,
Nobori Tadahito,
Schmutz Marc,
Lehn JeanMarie
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400826
Subject(s) - supramolecular chemistry , self assembly , molecule , crystallography , hydrogen bond , materials science , acceptor , supramolecular assembly , electron acceptor , nanotechnology , chemical physics , chemistry , photochemistry , crystal structure , organic chemistry , physics , condensed matter physics
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 m M ) 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.