Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 11, Issue 22, Pages 6666-6672Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200500565
Keywords
aggregation; dendrimers; fullerenes; hydrogen bonds; self-assembly
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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 tertbutoxycarbonyl (Boc)-protected 2ureido-4-[1H]pyrimidinone precursor possessing an alcohol function with fullerodendrons bearing a carboxylicacid 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 H-1 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.
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