Fullerene-bound dendrimers. Soluble, isolated carbon clusters

The coupling of compact dendritic macromolecules with prefunctionalized fullerenes is now described. This synthetic strategy, involving two species containing a precise number of functional groups, gives greater control over the formation of polymer-fullerene hybrid structures. Phenol-functionalized...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 115:21
Main Authors Wooley, K.L., Hawker, C.J., Frechet, J.M.J., Wudl, F., Srdanov, G., Shi, S., Li, C., Kao, M.
Format Journal Article
LanguageEnglish
Published United States 20.10.1993
Subjects
400102 - Chemical & Spectral Procedures
400201 - Chemical & Physicochemical Properties
CARBON
CHEMICAL REACTIONS
CHROMATOGRAPHY
DECOMPOSITION
ELEMENTS
FULLERENES
HYDROLYSIS
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
LYSIS
MAGNETIC RESONANCE
NONMETALS
NUCLEAR MAGNETIC RESONANCE
ORGANIC COMPOUNDS
ORGANIC POLYMERS
POLYMERS
RESONANCE
SEPARATION PROCESSES
SOLID CLUSTERS
SOLUBILITY
SOLVOLYSIS
SYNTHESIS
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Summary:The coupling of compact dendritic macromolecules with prefunctionalized fullerenes is now described. This synthetic strategy, involving two species containing a precise number of functional groups, gives greater control over the formation of polymer-fullerene hybrid structures. Phenol-functionalized fullerenes have been prepared by reaction of C[sub 60] with bis(p-methoxyphenyl)diazomethane followed by hydrolysis of the methyl ethers with BBr[sub 3]. This synthesis has been tailored to yield a 6-6 bridged methano fullerene derivative carrying only two phenolic sites as the major product. Polyether dendrimers prepared by the convergent synthesis route are ideally suited for attachment to phenol-functionalized buckyballs since they carry a single electrophilic site at their focal point, and their attachment to phenolic moieties has been studied extensively. The formation of fullerene-bound dendrimers was accomplished by reaction of each of the two phenolic groups located at the surface of the functionalized fullerene with the single benzylic bromide group at the focal point of a fourth-generation dendrimer in the presence of K[sub 2]CO[sub 3]. Purification by flash chromatography or precipitation gave only partial separation of the products; as a result, preparative SEC was used to obtain samples of each of the products. A [sup 1]H NMR spectrum of the desired product, in which two dendrimers are attached to the surface of the fullerene, is shown. 9 refs., 2 figs.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00074a075