Highly water soluble [60]fullerene (C60) end‐capped vinyl ether (VE) oligomers with well‐defined structure were synthesized by living cationic polymerization technique. The addition reaction between 1‐octynylfulleride anion and oligomeric cationic species of VEs with pendant acetoxyl or malonic ester functions afforded the precursor C60 end‐capped oligomers. The living VE oligomers were prepared by living cationic polymerization of diethyl 2‐(vinyloxy)ethylmalonate (VOEM) and 2‐acetoxyethyl vinyl ether (AcOVE) by the CH3CH(OR)Cl/ZnI2 [R = CH2CH2OCOCH3 and CH2CH2CH(COOEt)2, respectively] initiating system. The precursors were obtained as dark brown gummy solid in 33 and 72% yield for AcOVE and VOEM, respectively. UV‐vis and 13C NMR spectroscopy indicated the formation of 1,2‐disubstituted dihydrofullerene derivatives. Hydrolysis of the precursors proceeded quantitatively to give the water‐soluble C60 end‐capped oligomers having oligo(sodium 2‐vinyloxyethylmalonate) [oligo(VOEMNa)] and oligo(2‐hydroxyethyl vinyl ether) [oligo(HOVE)] moieties. Solubility measurements revealed the water‐soluble C60 end‐capped oligomer with oligo(VOEMNa) chain to have the excellent aqueous solubility compared to that of the water‐soluble C60 derivatives thus far known; the maximum solubility in water is 96.6 mg/mL, which corresponds to 25.9 mg/mL of the C60 moiety. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 3578–3585, 2000

SUMMARY: Water-soluble fullerene-bearing pullulans were successfully prepared by the addition reaction of azide-substituted pullulans with fullerene C 60 . The chemical structure of the products was characterized by IR, UV, and NMR spectroscopy. It was found that the saturation solubility of the C 60 moiety strongly depends on the degree of substitution (DS) of the sample, indicating that an optimum DS value of the C 60 moiety exists for its aqueous solubility.

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