Photochemical Synthesis of Fulleromulticarboxylates and Their
Langmuir-Blodgett Film Formation
GAN Liangbing, HUANG Chunhui
(College of Chemistry and Molecular Engineering, State Key Laboratory
of Rare Earth Material Chemistry and Applications, Peking University,
Beijing, 100871, China)
Abstract:
Photolysis of aminopolycarboxylates with C60 has been shown
to be an effective method for the preparation of isomerically pure fullerene
derivatives. A series of fullerroaminopolycar- boxylate derivatives have
been prepared by this method. For example, glycine esters react with
C60 to give C60(ROOCCHNHCHCOOR), the mechanism of
which is proposed to involve complicated bond breaking and formation
processes. Aminoacid esters with secondary and tertiary amino groups can
add to C60 by simply losing two H atoms. Irradiation of
tetramethyl ethylenediaminetetraacetate(EDTA) with C60 yields
the EDTA containing fullerene monoadduct
C60(MeOOCCH)2NCH2CH2N(CH2COOMe)2.
Compared to well-known 1, 3-dipole addition method of
fulleropyrrolidine preparation, the photoreaction reported here avoids
the use of aldehydes or ketones and is specially suited for the preparation
of the fullerene containing complexones such as the EDTA C60
derivative. Langmuir-Blodgett film formation and the photoelectric
properties of these fulleropyrrolidine compounds are investigated. Due
to the presence of hydrophilic groups the derivatives form stable and
transferable monolayer. By using metal ion sonlution as the subphase, metal
complexes of the fullerocarboxylic derivatives are prepared at the
air/water interface. Photoelctrical behavior of the LB film fabricated
on ITO are studied under various conditions. For most of the compounds
electrons flow from the electrolyte through the LB film to the ITO. The
quantum yield of the fullerene derivatives can reach 8%.
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