Founded in 1993
  Year: 1997 | Volume: 5 | Issue: 3 | Pages: 139-141
  Original Article
  SYNTHESIS AND CHARACTERIZATION OF WATER-SOLUBLE BIOLOGICALLY ACTIVE C60(OH)24
Aleksandar DJORDJEVIC, Mirjana VOJINOVIC-MILORADOV, Nadezda PETRANOVIC, Aleksandar DEVECERSKI, Gordana BOGDANOVIC, Jasna ADAMOV
  DOI:
  Abstract:
  Background: Molecule C60 is a new third allotropic modification of carbon, which is chemically reactive and thus differs from graphite and diamond. Since it dissolves very weakly in organic solvents, and is practically insoluble in polar solvents, the application of C60 is inabled in living systems. The functionalization of C60 by polar, hydroxylic groups, yields the polyhydroxy-derivative, fullerol, which is soluble in water. In this paper the method for synthesis of water-soluble polyhydroxy-derivative of C60 is described.
Methods: In two-step synthesis of of C60(OH)24 the first phase is bromination of C60 to C60Br24 with elementary bromine with the catalyst FeBr3. By the substitution of bromine atoms with hydroxyl groups in alcali water medium C60(OH)24 is obtained in high yield.
Results: Bromine derivative is orange powder, weakly soluble in dimethylsulfoxide. In the thermogravimetric analysis of C60Br24 the theoretical loss of 24 bromine atoms is registered, which is in accordance with the empirical formula. Polyhydroxy-derivative of fullerene is a brown amorphous substance, soluble in water. The IR spectrum of C60(OH)24 contains characteristic bands for hydroxyl group and C-O bond, which is the proof for the substitution of bromine from C60Br24 with the hydroxyl group. 13C NMR spectrum of water-soluble derivative contains one sharp peak at d 77.7 ppm which is significant for the carbon atom bonded to hydroxyl group.
Conclusion: This method for synthesis yields the water-soluble derivative C60(OH)24 in short time and in high yield. Polyhydroxy-derivative can take part in further synthesis of new medicaments. This molecule could be a potential transporter of active principle through the cell membrane.
  Key words: C60(OH)24, water-soluble C60 derivative; Synthesis; Characterization, IR, TG
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Founder, owner and publisher: Oncology Institute of Vojvodina, Serbia
Online since 1997 (Abstracts only); 2000 (Abstracts and Full text)
ISSN: 0354-7310 eISSN: 1450-9520