4
ordered one-dimensional stacks. The head-to-tail donorꢀ
acceptor supramolecular polymer reportedby Martin etal.
5
is a rare example, in which a tetrathiafulvalene based
Scheme 2. Possible Pathway for the Formation of 2
tweezer is covalently attached to C60 and acts as the host
for the C60 cage from another molecule. The crystal struc-
ture of the iridium metal complex C Ir(CO)Cl(bobPPh )
6
0
2 2
also shows chelation of the C by the phenyl groups of the
6
0
6
phosphine ligand from another molecule. So far little
effort has been devoted to the preparation of noncova-
7
lently bonded fullerene dimers. In contrast, a number of
8
covalently bonded dimers have been reported.
We have reported the preparation of open-cage
fullerene derivative 1 through a peroxide-mediated
9
pathway. The orifice of 1 is relatively large to encap-
1
0
sulate one water molecule readily at rt. Here we report
the conversion of 1 into compound 2, which forms a
dimeric supramolecule through head-to-tail and back-
to-back πꢀπ interactions.
Scheme 1. Synthesis of Compounds 2 and 3
3 (Scheme 1). Compound 3 was also observed as a minor
byproduct in the formation of 2 from 1.
The conversion of 1 to 2 involves replacement of one
carbonyl group by an oxygen atom and elimination of two
hydroxyl groups. It was an unexpected reaction. The
attempted reaction was aimed at hydrolysis of the imino
groups. A proposed mechanism for the conversion is
9
a
Compound 1 was prepared as previously reported.
Stirring a CH Cl solution of 1 with excess water in the
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2
presence of TsOH resultedin complete conversion of 1 into
an unknown product with high polarity as indicated by
TLC. Chromatography on silica gel eluting with CH Cl /
2
2
CH OH transformed the unknown product into com-
3
pound 2 as a green band. It was not possible to characterize
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