title: A highly directional fourfold hydrogen-bonding motif for supramolecular structures through self-assembly of fullerodendrimers.
abstract: Supramolecular dendrimers resulting from the dimerization of fullerene-functionalized dendrons through a quadruple hydrogen-bonding motif were prepared. The synthetic strategy is based on the esterification of a tert-butoxycarbonyl (Boc)-protected 2-ureido-4-[1H]pyrimidinone precursor possessing an alcohol function with fullerodendrons bearing a carboxylic acid unit at the focal point. Subsequent acidic treatment to cleave the protecting group and reaction of the resulting amine with octylisocyanate affords the targeted compounds. As demonstrated by the results of MALDI-TOF mass spectrometry and 1H NMR spectroscopy, both of the 2-ureido-4-[1H]pyrimidinone derivatives form self-assembled dimers spontaneously through hydrogen-bonding interactions, thus leading to supramolecular structures containing two or ten fullerene moieties.
authors.affiliation: Groupe de Chimie des Fullerènes et des Systèmes Conjugués, Laboratoire de Chimie de Coordination du CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France.
authors.forename: Uwe
authors.initials: U
authors.lastname: Hahn
authors.forename: Juan J
authors.initials: JJ
authors.lastname: González
authors.forename: Elisa
authors.initials: E
authors.lastname: Huerta
authors.forename: Margarita
authors.initials: M
authors.lastname: Segura
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Eckert
authors.forename: François
authors.initials: F
authors.lastname: Cardinali
authors.forename: Javier
authors.initials: J
authors.lastname: de Mendoza
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Nierengarten
mesh_terms: D037741:Fullerenes / Q000737:chemistry*; D006860:Hydrogen Bonding; D046911:Macromolecular Substances / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D015394:Molecular Structure; D012015:Reference Standards; D013237:Stereoisomerism
chemical_list: D037741:Fullerenes; D046911:Macromolecular Substances