Synthesis and characterisation of C-60 derivatives containing functionalised anthraquinone groups and an unusual fullerene-stabilised cation

Journal article

The ortho-anthraquinonedimethane dienophiles prepared in situ from 1,4-dihydroxy-2,3-bis(bromomethyl)-anthraquinone and 1,4-dimethoxy-2,3-bis(bromomethyl)anthraquinone respectively react with the fullerene C60 to give the anthraquinone derivatives: dihydroxy-anthraquinone-C60 and dimethoxy-anthraquinone-C60. The former compound with sodium butoxide and 15-crown-5 gives the bis(sodium-15-crown-5)dioxo-anthraquinone-C60. The dimethoxy-anthraquinone-C60 reacts with [Ru(PPh3)2(NO)Cl] to form the bis-adduct {[η2-(dimethoxy-anthraquinone-C60)][Ru(PPh3 )2(NO)Cl]}. The electrochemistry of the dihydroxy- and dimethoxy-anthraquinone-C60 derivatives has been studied by cyclic voltammetry and, in contrast to 1,4-dihydroxy-2,3-dimethylanthraquinone, the compound dihydroxy-anthraquinone-C60 shows two separate one electron oxidations at lower potentials strongly suggesting a relatively rare example of a fullerene stablised cation.

Authors: Bidell, W; Compton, R; Eklund, J; Green, M; Rebbitt, T

• Publication status: Published
• Journal: JOURNAL OF ORGANOMETALLIC CHEMISTRY
• Volume: 562
• Issue: 1
• Pages: 115-122
• Publication date: 1998-07-10
• DOI: 10.1016/S0022-328X(98)00436-7
• ISSN: 0022-328X
• Language: English
• Keywords: anthraquinone derivatives; electrochemistry; ruthenium complexes; fullerenes