Synthesis of fullerenols from halofullerenes

Pavel A. Troshin, Antonina S. Astakhova, Rimma N. Lyubovskaya

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

Halogenated fullerenes were used as reagents to prepare fullerenols. Depending on reaction conditions two types of substances (complex mixtures of products with average compositions C60OnHm, n=10-26, m=14-30 and C60OnHmMk, M = K, Na; n = 17-24, m = 16-28, k = 3-8) possessing essentially different water solubility were obtained. Highly soluble metal-containing species are most likely ionic compounds similar to metal derivatives of alcohols-alcoholates. An electron withdrawing effect of the carbon cage could make alkali metal fullerenolates (C60(OH)x(OM)y) inert towards hydrolysis. Halogens were selectively substituted when fullerene bromides and chlorides were treated with silver trifluoroacetate. Fullerenol esters C 60(OOCCF3)n formed were then hydrolyzed to form C60(OOCCF3)x(OH)y. Attempts to cleave all ester groups in C60(OOCCF3)x(OH) y failed in acidic media, while alkaline hydrolysis was accompanied by unselective polyhydroxylation of the fullerene cage.

Original languageEnglish
Pages (from-to)331-343
Number of pages13
JournalFullerenes Nanotubes and Carbon Nanostructures
Volume13
Issue number4
DOIs
Publication statusPublished - Oct 2005
Externally publishedYes

Keywords

  • C
  • C
  • Fullerenes
  • Fullerenols
  • Halofullerenes

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