A highly directional fourfold hydrogen-bonding motif for supramolecular structures through self-assembly of fullerodendrimers.
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.
Hahn
Uwe
U
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.
González
Juan J
JJ
Huerta
Elisa
E
Segura
Margarita
M
Eckert
Jean-François
JF
Cardinali
François
F
de Mendoza
Javier
J
Nierengarten
Jean-François
JF
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
D037741:Fullerenes; D046911:Macromolecular Substances