Synthesis of a novel [60]fullerene pearl-necklace polymer,poly(4,4′-carbonylbisphenylene trans-2-[60]fullerenobisacetamide) |
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Authors: | Lixin Xiao Hidekazu Shimotani Masaki Ozawa Jing Li Nita Dragoe Kazuhiko Saigo Koichi Kitazawa |
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Abstract: | A novel [60]fullerene pearl-necklace polymer, poly(4,4′-carbonylbisphenylene trans-2-[60]fullerenobisacetamide), was synthesized by a direct polycondensation of trans-2-[60]fullerenobisacetic acid with 4,4′-diaminobenzophenone in the presence of large excesses of triphenyl phosphite and pyridine. In the present polymer, [60]fullerene pearls and diamine linkers were attached to each other by methano-carbonyl connectors. The molecular weight Mw of the polymer was determined to be 4.5 × 104 on the basis of the TOF-MS, and a GPC analysis of the polymer using polystyrene standards showed a weight-average molecular weight of 5.3 × 104. The UV-vis spectrum of the resultant polymer in N,N-dimethylacetamide (DMAc) exhibited a broad absorption (λmax 310 nm, ε 2.1 × 104 L · mol−1 · cm−1), tailing to longer wavelengths, and a fluorenscence peak centered at 550 nm was observed in DMAc. There was observed a large downfield-shift of the cyclopropane methyne proton in the 1H-NMR spectra from 4.57 ppm of the ethyl ester to 5.78 ppm of the polyamide. These observations indicate that the present polyamide is a high-molecular-weight [60]fullerene pearl-necklace polymer and that the cyclopropane rings are efficient to make the [60]fullerene cages and the diamine components conjugatable. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 3632–3637, 1999 |
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Keywords: | trans-2 [60]fullerene pearl-necklace polymer polyamide synthesis |
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