A novel perylene diimide-based tetrahedral molecule: Synthesis, characterization and self-assembly with gold nanoparticles

Article abstract of DOI:10.1007/s12039-010-0072-1

In this study, a novel tetrahedral molecule TPPY was successfully designed and synthesized. The self-assembly of TPPY with gold nanoparticles (Au NPs) in toluene has also been investigated. The aggregation morphologies of Au NPs can be controlled to produce different aggregate structures by changing the concentration of ligand TPPY. Indian Academy of Sciences.

Full text of DOI:10.1007/s12039-010-0072-1

J. Chem. Sci., Vol. 122, No. 6, November 2010, pp. 839–846. © Indian Academy of Sciences.
A novel perylene diimide-based tetrahedral molecule: Synthesis,
characterization and self-assembly with gold nanoparticles
1,
2
2
2
2
JUN-BO LI *, XIANG-LIN YU , JING FU , XIWEN LIU and YANG ZENG
1
Hubei Novel Reactor and Green Chemical Technology Key Laboratory, Key Laboratory for Green
Chemical Process of Ministry of Education, Wuhan Institute of Technology, China
2
Department of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan,
Hubei Province, China
e-mail: jbli@mail.wit.edu.cn
MS received 18 November 2009; revised 16 March 2010; accepted 2 September 2010
Abstract. In this study, a novel tetrahedral molecule TPPY was successfully designed and synthesized.
The self-assembly of TPPY with gold nanoparticles (Au NPs) in toluene has also been investigated. The
aggregation morphologies of Au NPs can be controlled to produce different aggregate structures by
changing the concentration of ligand TPPY.
Keywords. Gold nanoparticles; perylene diimide; self-assembly; aggregation.
1. Introduction
Comparing to the flexible linkers, the rigid linkers
are easier to control the uniformity of Au NPs ag-
47
Recently, much attention has been focused on the
perylene diimide-based red chromophores, due to
their unique chemical, thermal, and photochemical
stability. These chromophores show various possible
gregation. For example, Andres et al. have obtained
an equal distance aggregation of Au NPs by a rigid
molecule of aryl di-isonitrile [1,4-di(4-isocyano-
48
phenylethynyl)-2-ethylbenzene]; Chen et al. have
1
applications in fluorescent solar collectors , light
prepared a Au-MPCs based two-dimensional film
with a rigid molecule 4,4′-thiobisbenzenethiol. In this
paper, we report the controlling of the self-assembly
of Au NPs with a rigid molecule TPPY. The tetra-
hedral structure of TPPY can prohibit π–π stacking
of perylenetetracarboxylic acid diimide. When
TPPY assembled with the Au NPs, the strong π–π
stacking of perylene unit was prohibited, which sug-
gested the aggregation of Au NPs was only influ-
enced by the structure of TPPY. Although the
coordination of pyridine with the surface of Au NPs is
weaker than that of thiols, this relative weak coordina-
tion might be useful in the reversible aggregation of
2
3,4
5
emitting diodes , dye lasers , molecular switches ,
6–8
and photovoltaic devices. They are highly absorb-
5
–1
–1
ing in the visible to near-IR region (ε ≈ 10 M cm )
and emit fluorescene with quantum yields near
9,10
11,12
unity. Perylene based chromophoric arrays
are
promising components for the construction of opti-
13,14
cal and electronic molecular devices.
The ability to assemble nanoparticles with con-
15–21
trollable size and shape
is of great interest, due
22–26
to their potential applications in sensors,
cata-
27,28
29–35
lysts
and optoelectronic nanodevices.
The con-
trollable size, shape and properties of the individual
nanoparticle building blocks via self-assembly com-
bining with the properties of organic molecules on the
47
Au NPs. The controlled aggregation of perylene-
tetracarboxylic acid diimide derivatives protected
Au NPs is useful for the construction of nanoparti-
cles-based photovoltaic devices in the future.
gold surface lead to the enhancement of device prop-
36,37
erties.
porphyrin,
assembling with the gold nanoparticles (Au NPs)
Nowadays, the chromophores such as
38,39
40–42
43
fullerene,
OPV based molecules
2. Experimental
44,45
have been reported widely.
However, only few
2.1 Materials and methods
literatures have been reported on the perylene diim-
46
ide based chromophores assembling with them.
All solvents were purified according to standard
procedures. Reactions were monitored by thin-layer
*For correspondence
839

840
Jun-Bo Li et al
chromatography on glass plates coated with SiO
2.2b Synthesis of TPPY: Tetra(4-aminophenyl)
methane (7) (26 mg, 0⋅07 mmol), 4 (300 mg,
2
2
F254. The plates were inspected by UV light or in I
vapor. Column chromatography was performed on 0⋅28 mmol), and imidazole (150 mg) were stirred
1
13
silica gel (160–200 mesh). H and C NMR spectra under argon at reflux for 3d in toluene (60 mL). The
were recorded on Bruker AV 400 (400 and reaction mixture was washed with water twice and
100 MHz, respectively) at ambient temperature. then dried over anhydrous sodium sulphate. The
They were referenced using their residual solvent as solvent was removed in vacuo and the residue was
the internal standard. The chemical shift values were then purified by silica gel chromatography with
expressed as δ values, and the coupling constants CH Cl /methanol (10 : 1) as eluant to afford the
2
2
1
values (J) are in Hertz. The following abbreviations title compound (150 mg, 46% yield). H NMR
were used for signal multiplicities: s singlet; d dou- (400 MHz, CDCl ), δ 8⋅51 (d, 8H, J = 4⋅9 Hz), 8⋅26
3
blet; t triplet; m multiplet. Matrix-assisted laser de- (s, 8H), 8⋅18 (s, 8H), 7⋅31–7⋅33 (m, 16H), 7⋅11–7⋅26
sorption ionization time-of flight (MALDI–TOF) (m, 40H), 6⋅79–6⋅84 (m, 32H), 5⋅30 (brs, 8H), 1⋅28
13
mass spectra were performed on Bruker Biflex III (s, 72H), 1⋅23 (s, 72H). C NMR (100 MHz,
MALDI–TOF spectrometer. The UV/Vis spectra of CDCl ) δ 31⋅4, 34⋅4, 42⋅8, 64⋅5, 119⋅3, 119⋅4, 119⋅5,
3
Au NPs colloid before and after ligand exchange 120⋅0, 120⋅2, 120⋅4, 121⋅1, 121⋅8, 122⋅7, 123⋅1,
were measured at room temperature by a Hitachi 126⋅6, 126⋅7, 127⋅7, 132⋅1, 133⋅0, 133⋅1, 133⋅4,
U-3010 spectrophotometer. Fluorescence spectra 145⋅9, 146⋅2, 147⋅4, 150⋅0, 152⋅7, 152⋅8, 155⋅9,
were obtained on Hitachi F-4500 fluorimeter. TEM 156⋅3, 163⋅4, 163⋅5. MALDI–TOF: calcd, 4609⋅4
+
+
micrographs were taken from JEOL JEM-1011 [M] , observed: m/z 4609⋅6 [M] , anal. Calcd. (%)
microscope with an acceleration voltage of 100 kV. for C H N O : C, 79⋅47; H, 5⋅77; N, 3⋅65.
305 264 12 32
The samples were prepared by dropping the corre- Found: C, 79⋅43; H, 5⋅76; N, 3⋅71.
sponding solution of Au NPs onto carbon-coated
copper grids.
2.2c Synthesis of TPOT: Tetra(4-aminophenyl)
methane (7) (26 mg, 0⋅07 mmol), 3 (307 mg,
0⋅28 mmol), and imidazole (150 mg) were stirred in
toluene (60 mL) under argon at reflux for 3d. The
reaction mixture was washed with water twice and
then dried over anhydrous sodium sulphate. The
solvent was removed in vacuo and the residue was
then purified by silica gel chromatography with
CH Cl as eluant to afford the title compound
2.2 Synthetic procedures of TPPY and TPOT
2.2a Synthesis of N-[1-(4-pyridyl)methyl]-1, 6, 7,
12-tetra(4-tert-butylphenoxy)-perylene-3,4-anhydride-
9, 10-tetracarboxylic Imide (4): 1, 6, 7, 12-tetra(4-
tert-butylphenoxy)-perylene-3,4,9,10-tetracarboxylic
Bisanhydride (2) (0⋅50 g, 0⋅5 mmol), 4-(amino-
methyl)pyridine (11 μL, 0⋅1 mmol), and imidazole
(200 mg) were stirred in toluene (30 mL) under
argon at reflux for 2 h. The reaction mixture was
washed with water twice and then dried over
anhydrous sodium sulphate. The solvent was
removed in vacuo and the residue was then purified
by silica gel chromatography with CH Cl /methanol
2
2
1
(210 mg, 64% yield). H NMR (400 MHz, CDCl ), δ
3
8⋅51 (d, 8H, J = 4⋅9 Hz), 8⋅24 (s, 8H), 7⋅32 (d, 8H,
J = 8⋅0 Hz), 7⋅17–7⋅24 (m, 32H), 7⋅11 (d, 8H,
J = 8⋅0 Hz), 6⋅79-6⋅84 (m, 32H), 4⋅10 (brs, 8H),
13
0⋅83–1⋅67 (m, 212H), C NMR (100 MHz, CDCl )
3
163⋅4, 156⋅0, 155⋅9, 152⋅9, 152⋅8, 147⋅2, 147⋅2,
146⋅2, 133⋅4, 133⋅0, 132⋅1, 127⋅7, 126⋅6, 122⋅5,
120⋅6, 120⋅5, 120⋅0, 119⋅9, 119⋅7, 119⋅4, 119⋅4,
119⋅3, 34⋅3, 34⋅30, 31⋅8, 31⋅4, 31⋅4, 29⋅7, 29⋅3, 29⋅2,
28⋅1, 27⋅1, 22⋅6, 14⋅1. MALDI–TOF: calcd. 4694⋅ 4
2
2
(70 : 1) as eluant to afford the title compound
1
(80 mg, 74% yield). H NMR (400 MHz, CDCl ),
3
δ 8⋅52 (s, 2 H), 8⋅21–8⋅26 (m, 4H), 7⋅31 (d, 2H,
J = 4⋅0 Hz), 7⋅25 (d, 8H, J = 8⋅5 Hz), 6⋅81–6⋅83 (m,
8H), 5⋅30 (s, 2H), 1⋅65 (m, 8H), 1⋅25–1⋅29 (m, 36H).
+
+
[M] , observed: m/z 4694⋅6 [M] .
13
C NMR (100 MHz, CDCl ) δ 31⋅5, 34⋅4, 42⋅9,
3
2.3 Synthesis of TOAB-capped Au NPs
118⋅2, 119⋅3, 119⋅5, 119⋅8, 112⋅0, 120⋅2, 120⋅3,
120⋅6, 121⋅1, 121⋅5, 121⋅6, 121⋅7, 121⋅9, 122⋅3, The TOAB-capped Au NPs were prepared according
46
122⋅6, 123⋅2, 126⋅7, 126⋅8, 126⋅9, 132⋅8, 133⋅0, to the reported method. Tetra-n-octylammonium
133⋅4, 146⋅0, 146⋅2, 147⋅4, 147⋅7, 147⋅8, 149⋅8, bromide (TOAB) (34⋅7 mg in 0⋅67 mL of toluene)
152⋅5, 152⋅6, 155⋅8, 156⋅0, 156⋅5, 159⋅9, 163⋅2, was added to a solution of HAuCl ⋅4H O (10 mg in
4
2
163⋅4.
0⋅33 mL of deionized water) and shaken in a separa-

A novel perylene diimide-based tetrahedral molecule
841
tory funnel. After the yellow water layer became characteristic absorption red shifted to 458 nm,
colourless, the water layer was removed. The result- 550 nm and 593 nm in compound TPPY due to the
ing solution was stirred vigorously in a 5 mL round- electron transfer from the pyridine to perylene unit.
bottom flask while a freshly prepared solution At the same time, the fluorescence spectra showed
(9⋅6 mg NaBH in 0⋅17 mL of deionized water) was that the maximum emission band located at 620 nm
4
added after which the solution became darkened.
The water layer was removed by extraction after 4 h
of stirring and then the toluene layer was washed for
three times with deionized water (1 mL for each
time).
2.4 Self-assembly of TPPY with TOAB-capped
Au NPs
The TPPY with different concentration in toluene
was added to the Au NPs solution (18⋅8 nM and
0⋅47 μM) in the dark and stirred for 2 min at room
temperature. The pyridine groups were allowed to
undergo a place-exchange reaction with TOAB-
capped Au NPs. Then the UV-vis spectra were
detected (delete the absorption of TPPY).
3. Results and discussion
3.1 Synthesis and characterization of the perylene
diimide ligand TPPY and its derivative TPOT
The synthesis of TPPY and TPOT was shown in
50,51
scheme 1.
A mixture of 1,6,7,12-tetra(4-tert-
butylphenoxy)-perylene-3,4,9,10-tetracarboxylic bis-
anhydride (2) and N-octyl-1,6,7,12-tetra(4-tert-
butylphenoxy)-perylene-3,4-anhydride-9,10-tetracar
boxylic imide (3) was obtained by partial sapo-
nification of the corresponding N,N′-di(8-amino-
octyl)-1,6,7,12-tetra(4-tert-butylphenoxy)-perylene-
3,4,9,10-tetracarboxylic diimide (1). N-[1-(4-
pyridyl)methyl]-1,6,7,12-tetra(4-tert-butylphenoxy)-
perylene-3,4-anhydride-9,10-tetracarboxylic imide
(4) was obtained by the imidization of compound 2
Scheme 1. Synthetic route of TPPY and TPOT. (a)
KOH, isopropyl alcohol, H O, reflux, 10 h; (b) 4-
2
(aminomethyl)pyridine, imidazole, reflux, 2 h; (C) ani-
line, 200°C, 5 min, then, HCl/CH OH, reflux, 10 h; (d)
3
nitric acid, 0°C to RT, 10 h; (e) NH NH , Pd/C,THF,
2
2
reflux, 4 h; (f) imidazole, toluene, reflux, 3d.
52
and 4-(aminomethyl)pyridine in toluene. Com-
pounds of TPPY and TPOT were obtained by the
same reaction of 4 and 3 with tetra(4-amino-
phenyl)methane (7) in toluene, respectively.
The optical absorption and fluorescence proper-
ties of the compounds TPPY and TPOT (figure 1)
and the relative fluorescence quantum yield (table 1)
were investigated. The absorption band of the pery-
lene unit in compound TPOT showed the character-
istic ∂–∂ transitions of the functionalized perylene
Figure 1. UV-Vis absorption and fluorescence spectra
-6
53,54
bisimide
: 455 nm (S0–S2 electronic transition),
of ligand TPPY and its derivative TPOT (1 × 10 M) in
CHCl .
3
55
545 and 588 nm (S0–S1 electronic transition). The

842
Jun-Bo Li et al
for compound TPOT, which red shifted to 624 nm 3.2 Self-assembly of TPPY with TOAB-capped
with relative decrease on intensity in comparison Au NPs
with compound TPPY. Meanwhile, the films of the
Fluorescence titration experiments were carried out
in toluene. A solution of TOAB-capped Au NPs in
toluene was titrated against a solution of ligand
TPPY in toluene and the resultant TPPY fluores-
cence was monitored. As shown in figure 4, the
fluorescence of TPPY was quenched as the Au NPs
were added. The result showed that the interaction
of the ligand with the Au NPs can lead to an effec-
compounds of TPPY and TPOT emitted red fluo-
rescence at 628 nm and 630 nm, respectively (figure
2). This kind of compound can be useful as a poten-
tial red emission material.
The UV-Vis spectra of the ligand TPPY with dif-
–6
–4
ferent concentration (from 1 × 10 M to 1 × 10 M)
showed that the characteristic absorbance of TPPY
had no change with the concentration increased (fig-
ure 3), which demonstrated that the tetrahedral
structure of TPPY prohibited the π–π stacking of
perylene unit in toluene. Therefore, the self-
assembly structure of Au NPs was only influenced
by the structure of TPPY. Meanwhile, the minimum
energy optimization of ligand TPPY was shown in
figure S1 with the MM2 minimum energy method,
which showed that the distance between optional
two pyridines is about 3 nm (see the supporting
information). We suggested that the aggregation of
Au NPs was able to control by such special structure
of ligand.
47
tive energy transfer.
Table 1. Photophysical properties of TPPY and TPOT.
a
UV λ (nm)
max
FL λ (nm)
max
ϕ
F
TPOT
TPPY
588
593
620
624
0⋅90
0⋅83
Figure 3. UV-Vis absorbance spectra of TPPY with
–6
–6
–5
different concentration (1 × 10 , 5 × 10 , 1 × 10 ,
–5
–5
–4
a
2 × 10 , 5 × 10 , 1 × 10 M, the width of cell is
0⋅1 cm).
N,N′-Di(2,6-diisopropylphenyl)-1,6,7,12-tetraphenoxy-
perylene-3,4,9,10-tetracarboxylic diimide (TPPI) as ref-
48
erence (fl ) 0⋅96 in CHCl ).
3
Figure 4. The fluorescence titration experiments of
TPPY with the TOAB-capped AuNPs. λ = 550 nm. The
ex
Figure 2. Normalized fluorescence spectra of com-
pounds TPPY and TPOT in solid film.
inset shows the PL intensity at 608 nm versus the volume
(μL) of Au NPs.

A novel perylene diimide-based tetrahedral molecule
843
As shown in figure 3, the special tetrahedral struc- The SP absorption band with a maximum at
ture of TPPY prohibits the π–π stacking interaction λ = 524 nm remained when the concentration of
–5
between the perylene units. The driving force for the TPPY was 1⋅25 × 10 M (r = 26⋅6). As the concen-
self-assembly of TPPY with Au NPs is the coordi- tration of TPPY increased, the SP absorption band
nation interaction which is weaker than the interac- of Au NPs red shifted from 524 nm to nearly
tions of thiols with gold nanoparticles. This weak 740 nm (figure 7), indicating the efficient self-
interaction would not only be affected by the ratio of assembly of TPPY with TOAB-capped Au NPs.
the ligand and Au NPs but also affected by the con-
centration of the solution.
The related TEM data were shown in figure 8. For
–5
the low concentration of TPPY (1⋅25 × 10 M), no
Optical spectra and microscopic data were used to obvious self-assembly behaviour was observed and
monitor the self-assembly process of the ligand the Au NPs with the diameter of nearly 5 nm were
TPPY with the TOAB-capped Au NPs. When the present (figure 8A). When the concentration of
–5
2
concentration of Au NPs was 18⋅8 μM, a titration TPPY was 5 × 10 M (r = 1⋅06 × 10 ), the Au NPs
experiment was carried out by adding different con- were able to self-assemble into large scale clusters
centration of ligand to the Au NPs. The surface with average diameter nearly 50 nm. Moreover,
plasmon (SP) absorption band (figure 5) of TOAB- when the concentration of TPPY increased to
–4
2
capped Au NPs decreased slightly and only red 1 × 10 M (r = 2⋅13 × 10 ), the observation of TEM
shifted 4 nm using a large excess of TPPY (r ≈ 2k, showed that the cluster structure of Au NPs was not
the definition of r, see the Supporting Information). changed, but some of clusters began to aggregate
This result showed that the interaction of TPPY (figure S2C). As the concentration increased to
–4
2
with Au NPs was weak at the low concentration of 2 × 10 M (r = 4⋅26 × 10 ), the Au NPs clusters
the Au NPs. The TEM data also proved that result, linked to each other forming a chain-like structure
which showed that the size of Au NPs (≈ 5 nm), be- (figure 8C). As the concentration continuously in-
–4
2
fore (figure 6a) and after (figure 6b) addition of an creased to 5 × 10 M (r = 10⋅6 × 10 ), the Au NPs
excess of TPPY, was nearly the same. aggregated into sphere-like structure with an aver-
When the concentration of Au NPs was 0⋅47 μM, age diameter of nearly 200 nm (figure 8D). Unlike
the TPPY can efficiently assemble with them. Opti- the aforementioned cluster structure, this sphere-like
cal spectra and microscopic data were used to moni- structure consisted of many tight-aggregated Au
tor the self-assembly structures. UV-Vis absorption NPs. When the concentration of TPPY arrived at
–3
3
measurements were carried out in toluene, which 1 × 10 M (r = 2⋅13 × 10 ), some fusions happened
showed TPPY concentration-dependent behaviour. (figure S2E).
3.3 The self-assembly mechanism of TPPY with
TOAB-capped Au NPs
According to the optical spectra and microscopic
data, the aggregates of the TOAB-capped Au NPs
could be controlled at a Au NPs concentration of
0⋅47 μM. When the TOAB molecules on the surface
of Au NPs were displaced gradually by the pyridine
ligands in TPPY, the self-assembly of Au NPs took
place. When the concentration of the TPPY was
–5
5 × 10 M, TPPY displaced some of the TOAB
molecules leading to the aggregation of Au NPs.
However, in this concentration, the weak interac-
tions could not induce a large aggregation but
formed clusters consisting of many separated Au
Figure 5. UV-Vis spectra of the Au NPs. (a) TOAB-
–4
NPs. The reasons were as follows: (i) the big rigid
capped Au NPs (18⋅8 nM); (b) after adding 100 μL, 10 M
TPPY; (c) after adding 200 μL, 10 M TPPY; (d) after
structure of TPPY prohibited the tight-aggregation
–4
–4
adding 300 μL, 10 M TPPY; (e) after adding 400 μL,
of separated Au NPs; (ii) and the charge repulsion of
–4
10 M TPPY.
the unsubstituted TOAB molecules on the surface of

844
Jun-Bo Li et al
Figure 6. TEM images of (A) TOAB-capped Au NPs; (B) after the addition of ligand TPPY (400 μL,
–4
10 M).
Figure 7. UV-Vis spectra of the Au NPs self-assemble with different
–5
concentration of TPPY. (a) Au NPs (0⋅47 μM); (b) [TPPY] = 5 × 10 M;
–4
–4
(c) [TPPY] = 1 × 10 M; (d) [TPPY] = 2 × 10 M; (e) [TPPY] = 5 ×
–4
–3
10 M; (f) [TPPY] = 1 × 10 M (the width of cell is 0⋅1 cm).
Au NPs also prohibited the tight-aggregation of static repulsion between the TOAB molecules was
them. Continually increasing the concentration of disappeared which led to tight aggregation of the
ligand, more TOAB molecules were displaced by separated Au NPs. In this condition, the former
them. However, due to the large steric hindrance chain-like structure was destroyed, forming a
effect, the added TPPY exchanged the exterior sphere-like structure.
TOAB molecules of the clusters preferentially. The
former clusters linked to each other forming a chain-
4. Conclusions
like structure when the concentration of TPPY was
–4
2 × 10 M. Adding a large excess of the ligand
TPPY, the TOAB molecules on the surface of Au In conclusion, we have synthesized and character-
NPs were displaced by them thoroughly. Electro- ized two novel tetrahedral molecules TPPY and its

A novel perylene diimide-based tetrahedral molecule
845
–5 –5
Figure 8. TEM images of Au NPs with different concentration of TPPY: (A) 1⋅25 × 10 M; (B) 5 × 10 M;
–4
–4
the inset shows the high-magnification of a cluster; (C) 2 × 10 M; (D) 5 × 10 M.
derivative TPOT. The self-assembly of TPPY with of Technology under grant No. GCP200905, and the
Au NPs in toluene was also investigated, the results Science Research Fund of Wuhan Institute of Tech-
showed that the most effective assembly of TPPY nology (No. 10092021).
and Au NPs could take place at Au NPs concentra-
tion of 0⋅47 μM. Meanwhile, in that concentration,
the aggregation of Au NPs was controllable by
Supplementary information
The figure of TPPY with the minimum energy
changing the concentration of the ligand TPPY.
1
simulation, the definition of r and the original H
Such organic–inorganic hybrid nanoscale materials
13
NMR, C NMR, and MALDI–TOF spectra of all
of perylene capped Au NPs with control over the
new compounds are provided in supplementary in-
shape, bring new and exciting perspectives to photo-
formation (see www.ias.ac.in/chemsci).
and electronic-active materials and we are now pur-
suing their physical properties and potential applica-
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