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A Highly Directional Fourfold Hydrogen‐Bonding Motif for Supramolecular Structures through Self‐Assembly of Fullerodendrimers
Author(s) -
Hahn Uwe,
González Juan J.,
Huerta Elisa,
Segura Margarita,
Eckert JeanFrançois,
Cardinali François,
de Mendoza Javier,
Nierengarten JeanFrançois
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.200500565
Subject(s) - dendrimer , supramolecular chemistry , chemistry , hydrogen bond , amine gas treating , self assembly , polymer chemistry , fullerene , cleave , supramolecular assembly , stereochemistry , combinatorial chemistry , crystallography , organic chemistry , molecule , crystal structure , enzyme
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‐[1 H ]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 1 H 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.