Synthesis of a novel [60]fullerene pearl-necklace polymer, poly(4,4′-carbonylbisphenylene trans-2-[60]fullerenobisacetamide)

Lixin Xiao, Hidekazu Shimotani, Masaki Ozawa, Jing Li, Nita Dragoe, Kazuhiko Saigo, Koichi Kitazawa

Research output: Contribution to journalArticle

24 Citations (Scopus)

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 methanocarbonyl 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 15.3×104. 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 fluorescence 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.

Original languageEnglish
Pages (from-to)3632-3637
Number of pages6
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume37
Issue number18
DOIs
Publication statusPublished - 1999 Sep 15
Externally publishedYes

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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