Hahn Uwe, González Juan J, Huerta Elisa, Segura Margarita, Eckert Jean-François, Cardinali François, de Mendoza Javier, Nierengarten Jean-François
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.
Chemistry. 2005 Nov 4;11(22):6666-72. doi: 10.1002/chem.200500565.
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.
通过四重氢键基序使富勒烯功能化树枝状分子二聚化得到的超分子树枝状聚合物被制备出来。合成策略基于对具有醇官能团的叔丁氧羰基（Boc）保护的2-脲基-4-[1H]嘧啶酮前体与在焦点处带有羧酸单元的富勒烯树枝状分子进行酯化反应。随后进行酸性处理以裂解保护基团，并使所得胺与异氰酸辛酯反应得到目标化合物。基质辅助激光解吸电离飞行时间质谱（MALDI-TOF）和1H核磁共振光谱（1H NMR）的结果表明，两种2-脲基-4-[1H]嘧啶酮衍生物均通过氢键相互作用自发形成自组装二聚体，从而产生包含两个或十个富勒烯部分的超分子结构。
