Table 11 (continued)
Preparation method
Observations
References
comparison with the monofunctionalized C 60 derivatives. The
fluorescence lifetimes of the C 60
derivatives, were obtained using the
time-correlated single
Cis- and trans-functionalized bis-18crown-6 porphyrins self-assembled
with fullerene functionalized with
pyridine or alkyl ammonium cation
entities
Photo-induced electron-transfer
processes reported
Souza et al.
[152]
A self-assembled photoactive antenna
system containing GNP as the
central nanocore and appended
fullerene moieties as the
photoreceptive hydrophobic shell
was designed by functionalizing a
GNP with a thiol derivative of
fullerene
Upon suspension of fullerenefunctionalized GNPs (Au–S–C 60 ) in
toluene, formation of 5–30 nm
diameter clusters was observed. The
quenching of fluorescence emission
as well as decreased yields of triplet
excited state suggests the
participation of excited singlets in
the energy transfer to the gold
nanocore. Application of
electrophoretically deposited
Au–S–C 60 nanoassemblies on
optically transparent electrodes in
the photoelectrochemical conversion
of light energy was demonstrated
Sudeep et al.
[153]
The Diels–Alder reactions of masked obenzoquinones (MOBs) with [60]
fullerene afforded novel and highly
functionalized bicyclo-[2.2.2]octenone-fused [60]fullerene
derivatives
MOBs reactive with cyclohexa-2,4dienones undergo Diels–Alder
cycloadditions with [60]fullerene to
produce hitherto unknown, stable,
and highly functionalized bicyclo[2.2.2]-octenone derivatives. In light
of the mild conditions and
considerable generality, these
reactions are certainly noteworthy
Yen et al.
[154]
A variant of the Huisgen 1,3-dipolar
cycloaddition reaction provides a
new and convenient
functionalization of fullerenes
This method complements the widely
used Prato and Bingel–Hirsch
reactions. The derived, highly
functionalized cyclopentenone and
cyclopentenamine fullerene
compounds are suitable for further
functionalization upon hydrolysis
and may serve well in the synthesis
of new C 60 derivatives possessing
uncommon and interesting
properties
Zhou and
Magriotis
[155]
One-step preparation of
polyfunctionalized fullerene
derivatives by regioselective pentaaddition of an organocopper reagent
A functionalized aryl iodide was first
converted to the corresponding
Grignard reagent and then to a
copper reagent and finally allowed to
react with C 60 . The method allows
Zhong et al.
[156]
(continued)
Functionalized Nanoparticles and Chitosan-Based Functional Nanomaterials
25
Preparation method
Observations
References
comparison with the monofunctionalized C 60 derivatives. The
fluorescence lifetimes of the C 60
derivatives, were obtained using the
time-correlated single
Cis- and trans-functionalized bis-18crown-6 porphyrins self-assembled
with fullerene functionalized with
pyridine or alkyl ammonium cation
entities
Photo-induced electron-transfer
processes reported
Souza et al.
[152]
A self-assembled photoactive antenna
system containing GNP as the
central nanocore and appended
fullerene moieties as the
photoreceptive hydrophobic shell
was designed by functionalizing a
GNP with a thiol derivative of
fullerene
Upon suspension of fullerenefunctionalized GNPs (Au–S–C 60 ) in
toluene, formation of 5–30 nm
diameter clusters was observed. The
quenching of fluorescence emission
as well as decreased yields of triplet
excited state suggests the
participation of excited singlets in
the energy transfer to the gold
nanocore. Application of
electrophoretically deposited
Au–S–C 60 nanoassemblies on
optically transparent electrodes in
the photoelectrochemical conversion
of light energy was demonstrated
Sudeep et al.
[153]
The Diels–Alder reactions of masked obenzoquinones (MOBs) with [60]
fullerene afforded novel and highly
functionalized bicyclo-[2.2.2]octenone-fused [60]fullerene
derivatives
MOBs reactive with cyclohexa-2,4dienones undergo Diels–Alder
cycloadditions with [60]fullerene to
produce hitherto unknown, stable,
and highly functionalized bicyclo[2.2.2]-octenone derivatives. In light
of the mild conditions and
considerable generality, these
reactions are certainly noteworthy
Yen et al.
[154]
A variant of the Huisgen 1,3-dipolar
cycloaddition reaction provides a
new and convenient
functionalization of fullerenes
This method complements the widely
used Prato and Bingel–Hirsch
reactions. The derived, highly
functionalized cyclopentenone and
cyclopentenamine fullerene
compounds are suitable for further
functionalization upon hydrolysis
and may serve well in the synthesis
of new C 60 derivatives possessing
uncommon and interesting
properties
Zhou and
Magriotis
[155]
One-step preparation of
polyfunctionalized fullerene
derivatives by regioselective pentaaddition of an organocopper reagent
A functionalized aryl iodide was first
converted to the corresponding
Grignard reagent and then to a
copper reagent and finally allowed to
react with C 60 . The method allows
Zhong et al.
[156]
(continued)
Functionalized Nanoparticles and Chitosan-Based Functional Nanomaterials
25