Self-assembly facilitated and visible light-driven generation of carbon dots

Article abstract of DOI:10.1039/c7cc08876k

Carbon dots (CDs) with an absolute fluorescence quantum yield of 87% are facilely prepared via irradiation of self-assembled terthiophene amphiphile TTC4L in aqueous solution by mild visible light. Visible light irradiation of TTC4L triggers the production of superoxide radicals in water, which oxidize the closely packed terthiophene group into carbon dots. Our results reveal that the molecular self-assembly may act as important precursor for the generation of single molecule-like carbon dots; this method paves the way for the fabrication of CDs of high quality.

Full text of DOI:10.1039/c7cc08876k

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DOI: 10.1039/C7CC08876K
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Self-Assembly Facilitated Visible Light-Driven Generation of
Carbon Dots
Received 00th January 20xx,
Accepted 00th January 20xx
Tian Huang,a,b Tongyue Wu,a Zhiyang Zhu,a Li Zhao,c Haina Ci,b Xuedong Gao,a Kaerdun Liu,a
Junfang Zhao,d Jianbin Huanga,b and Yun Yan*a
DOI: 10.1039/x0xx00000x
www.rsc.org/
Carbon dots (CDs) with an absolute fluorescence quantum yield of precursors are also widely employed to obtain CDs, where
87% are facilely prepared via mild visible light irradiation of self- small molecules are treated with hydrothermal22 or
assembled terthiophene amphiphile TTC4L in aqueous solution. solvothermal23 cutting strategies, or subjected to microwave
Visible light irradiation of TTC4L triggers the production of pyrolysis,24 which finally results in nanometer sized carbon
superoxide radical in water which oxidizes the closely packed materials.
terthiophene group into carbon dots. Our result reveals that the
In this work, we show that molecular self-assembly can
close and ordered molecular arrangement in molecular self- facilitate generation of CDs under visible light irradiation.
assembly may act as important precursor for the generation of Different from the literature methods that require high voltage,
single molecule like carbon dots, which paves the way for temperature, strong acids, or involve the use of special
fabrication of CDs of high quality.
equipment, visible light irradiation of the vesicular self-
assembly of a terthiophene amphiphile TTC4L in water can
generate CDs with an absolute fluorescence quantum yield up
Last decades have witnessed the rapid development of
molecular self-assemblies owing to their potent application in
fabrication of advanced materials,
to 87%. Mechanism study shows that photo induced
1-4
-•
especially various smart
generation of superoxide radicals (O2
) triggered the
materials that are responsive to external stimulus, such as light,
temperature, pH, etc.5-7 Besides the responsiveness of
molecular self-assemblies, the ordered molecular arrangement
is also very useful in material science, such as creating
conductive materials,8 chiral self-assembled structures,9 and
various supramolecular polymers.10, 11 However, so far, the
carbonization of the terthiophene moiety, which finally leads
to generation of CDs. This work for the first time reports the
advantage of using molecular self-assembly as the precursors
for the fabrication of carbon dots, and the possibility to
generate dots with visible light (Scheme 1).
TTC4L was synthesized in our lab,25 which is an amphiphile
advantage of ordered molecular arrangement in molecular with a terthiophene group in the hydrophobic tail tethered to
a hydrophilic chelidamic acid head via an oxyl-butyl chain
(Scheme. 1). This molecule is able to self-assemble into
vesicles in water, and the size of the TTC4L vesicles is
concentration dependent.25 In the present study, vesicles with
diameter of 60-90 nm are formed in the 50 μM TTC4L aqueous
self-assemblies has been seldom exploited in preparation of
carbon dots (CDs).
As a prospective member of nanomaterials, CDs have
attracted intensive attention in the field of solar energy
conversion,12-14 bio-imaging,15, 16 as well as chemical sensing17,
18
owing to their stable photoluminescence (PL), low
cytotoxicity, and excellent biocompatibility. They are
ultrasmall fragments of carbon materials with tunable degree
of carbonization, which are usually fabricated from carbon
soot, graphite or carbon nanotubes via arc discharge,19 laser
ablation,20 or electrochemical oxidation.21 Molecular
Scheme 1. Illustration for the formation of TTC4L-CDs.
J. Name., 2013, 00, 1-3 | 1
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solution (Fig. 1a). The vesicular suspension of TTC4L displays new peak at 401.1 eV (N element in ammonium compound)
blue emission (Fig. 1b, black line) at 435 nm. However, the for N occur, suggesting a progressive photo oxidVaiteiwoAnrtipclreoOcnelisnes
DOI: 10.1039/C7CC08876K
1s
fluorescence shifts to 460 nm and keeps increasing (Fig. 1b) of TTC4L. The high-resolution XPS for the final purified TTC4L-
upon irradiation with a daylight lamp (25 mW cm-2). After 16 CDs can be decomposed into 3 main peaks from different
hours, the fluorescence reaches maximum, which is about 5 binding state of C1s electrons (Fig. 2b). The one at 284.5 eV can
folds of the original intensity, and the absolute FLQY amounts be assigned to the graphitic skeleton (sp2 C-C), while the one at
as high as to 87%. Meanwhile, the UV absorbance of TTC4L 285.5 eV indicates the presence of C-O bond and the C-C single
decreases (Fig. S1). 1H NMR measurements reveal the bond, and the peak at 288.0 eV signalizes C=O bond.
disappearance of signals corresponding to the terthiophene
group, indicating that TTC4L has undergone photochemical
reaction (Fig. S2). TEM observation manifests the formation of
small nanoparticles with average diameters of 2.7 nm ± 0.4 nm
(Fig. 1c, lower inset). A lattice spacing of 0.32 nm, manifest the
distance of the <002> facet of graphitic carbon,26, 27 can be
obtained with high resolution TEM (Fig. 1c, upper inset),
indicating the formation of carbon dots (denoted as TTC4L-
CDs). AFM measurement shows the average topographic
height of the obtained carbon dots are about 1.6 nm ± 0.3 nm
(Fig. S3). Obviously, the ultra-high fluorescence quantum yield
is from the light generated carbon dots. Fig. 1d reveals that the
TTC4L-CDs display a single exponential fluorescence lifetime of
2.5 ns, which is significantly different from the two lifetimes
observed for the original TTC4L vesicles (Fig. 1d and Tab.S1)
The surface state of the TTC4L-CDs was further examined
with Raman and FT-IR measurements. The Raman spectrum
reveals that the CDs display D and G bands at 1365 and 1570
cm-1 respectively (Fig. 2c), which are characteristics of carbon
materials. The relative intensity ratio of the D-band and the
crystalline G-band (ID/IG) is about 0.9, which is a very large
value indicating the presence of considerable defects30,31
.
Furthermore, FT-IR spectra (Fig. 2d) manifest the nearly
vanishing of the skeletal vibration of the pyridine ring at 1370
cm-1, the C-O-C asymmetric and symmetric stretching vibration
at 1100 and 1040 cm-1, and the out-of-plane vibration of
aromatic rings at 800 cm-1 in the TTC4L-CDs. However, the
symmetric and asymmetric stretching vibrations of C=O,
around 1409 cm-1 and 1565 cm-1 still remain there, but the
separation between the symmetric and asymmetric viberation
decreases by about 100 cm-1, suggesting the environment of
b
a
1200
p-0h
p-2h
p-4h
the C=O has changed drastically. Meanwhile,
a broad
800
p-6h
vibrational band characteristic of hydrogen bond is observed
at 3410 cm-1. These IR features suggest the presence of –COOH
groups on the surface of CDs. Indeed, the CDs display
reversible pH dependent fluorescence. The fluorescence
decreases as the pH decreases, probably due to the hydrogen
bonding between the CDs (Supplementary Fig. S6). Specially,
the asymmetric and symmetric vibration for -CH2- are also
observed at 2921 cm-1 and 2850 cm-1, indicating the
hydrophobic carbon chain of TTC4L is probably attached to the
surface of the CDs, too. It is possible that both the -COOH
groups and the pending alkyl chains are beneficial for the high
p-8h
p-12h
p-16h
400
p-24h
0
400
500
600
Wavelength (nm)
c
d
Prompt
TTC4L
TTC4L-CDs
100000
10000
1000
100
30
20
10
0
10
FLQY of the TTC4L-CDs through
a
surface passivation
mechanism20,28,29
.
1
0.1
1
2
3
4
5
0
500
1000
1500
a
b
4x104
Diameter (nm)
C1s 72.2%
Channel
O1s
Total
2x105
O1s 25.6%
284.5 (C=C sp2)
288.0 (C=O)
285.5 (C-O, C-C sp3)
Background
N1s 1.0%
S2p 1.3%
Figure 1
. a) TEM image of vesicles formed in 50 μM TTC4L. b) Fluorescence
C1s
3x104
2x104
1x104
spectra of 50 μM TTC4L aqueous solution irradiated by a daylight lamp
(25mW cm-2) at different times. Inset: Photos of the solution at different
irradiation time under 365 UV (from left to right). c) TEM image of the CDs
(upper inset: high resolution image of the CDs; lower inset: size distribution
of CDs). d) Fluorescence lifetime of TTC4L and the CDs
1x105
0
N1s
S2P
900
600
300
0
292 290 288 286 284 282 280
The FLQY is usually closely related to the composition and
surface groups of CDs28,29. X-ray photoelectron spectroscopy
(XPS) results (Fig. 2a) indicate that the CDs are mainly
composed of carbon and oxygen, with tiny amount of nitrogen
and sulphur. It is worth noting that the peak intensity of
nitrogen and sulphur in the original TTC4L solution is much
stronger than that in the irradiated sample (Supplementary Fig.
S4), suggesting the nitrogen and sulphur has gone away from
the CDs after light-irradiation. XPS measurement for samples
at different irradiating stages(Fig. S5) reveal that the content
of original S2p at 163.9 eV and N1s at 399.0 eV of TTC4L
decreases with increasing the irradiation time. Meanwhile, a
new peak at 168.2 eV (S element in sulfur dioxide) for S2p and a
Binding energy (eV)
Binding energy (eV)
1800
ν
(-COOH)
c
as
G band
d
D band
TTC4L
1600
1400
1200
1000
TTC4L-CDs
0.8
ν
(-COOH)
s
ν(-OH
)
0.4
0.0
ν(-CH )
2
1000
1500
2000
2500
3000
4000
3000 2000
1000
Wavenumber (cm-1)
Wavenumber (cm-1)
Figure 2. Surface-state characterizations of TTC4L-CDs. a) XPS spectrum of
TTC4L-CDs. b) High-resolution of C1s of XPS spectrum. c) Raman spectrum
of TTC4L-CDs. d) FT-IR spectrum of TTC4L-CDs.
2 | J. Name., 2012, 00, 1-3
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Unlike most CDs displaying excitation dependent
emission32,33, the emission of the TTC4L-CDs is excitation-
independent. As the excitation wavelength altered from 254
nm to 380 nm, the maximum emission wavelength remains
constant (Supplementary Fig. S7a), suggesting the emission is
originated from defects, rather from band-gap20,34. This is in
line with the large ID/IG value obtained in Raman measurement
(Fig. 2c). The defect facilitated emission of the TTC4L-CDs has a
narrow full width at half-maximum (FWHM) of only 70 nm
(Supplementary Fig. S7b), which is narrower than most of the
FWHMs of >100 nm for other CDs31. In combination with the
single exponential decay of the fluorescence lifetime, we infer
that single molecule-like CDs have been generated with light in
this work.
Excitingly, the single molecule-like CDs display two-photo
fluorescence properties. Fig. 3a reveals that upon exposure to
a near-infrared (NIR) femtosecond laser of 730 nm, emission of
the TTC4L-CDs occurs as well. With the logarithmic coordinate,
the linear slope is 1.89 which describes a clear quadratic
relationship between the excitation laser power and the
fluorescence intensity (Fig. 3b), confirming that excitation with
two NIR photons is responsible for the fluorescence of the
CDs35.
result (Fig. 4b, blue line) of EPR signal was quite consistent
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·
-
with the O2 signal. Control experimentDsOsIu: g10g.e10s3t9t/hCa7Ct Cn0o88E7P6RK
signal can be observed in the TTC4L aqueous system without
·
-
exposure to light (Fig. 4b, black line), indicating O2 is
generated by irradiating the TTC4L aqueous system with visible
·
-
light. The production of O2 is very crucial in the visible light
generated CDs. As a proof of this argument, when the reactive
·
-
O2 was consumed by degradation of organic dyes, such as
rhodamine B, the fluorescence of TTC4L only increases slightly,
·-
(Supplementary Fig. S9), confirming the important role of O2
in the formation of CDs.
The self-assembling ability of TTC4L is very crucial in the
light triggered generation of CDs. Upon dissolving TTC4L in a
good solvent such as ethanol, the fluorescence only slowly
increased by 1fold after 24 hours irradiation (Supplementary
Fig. S10). Furthermore, as the self-assembling ability is
enhanced by extending the hydrocarbon chain tethering the
coordinating head and the terthiophene group from 4 -CH2-
(TTC4L) to 8 -CH2- (TTC8L, Fig. 5a), the CDs can be generated
even faster. Fig. 5b shows the UV-vis spectra of TTC4L and
TTC8L aqueous solution, the stronger aggregated ability of
TTC8L than TTC4L lead to the increase of turbidity. In Fig.5c
and Supplementary Fig. S11 we show that the fluorescence
reaches maximum within 12 hours in the TTC8L system,
whereas it takes 16 hours in the TTC4L system. Different from
the 60-90 nm vesicles formed by TTC4L, TEM observation
reveals the formation of hexagonal structure of 2400 nm long
and 500 nm wide in the TTC8L system (Supplementary Fig.
S12a). However, the size and emission of the CDs obtained in
the TTC8L system is the same as that in the TTC4L system
(Supplementary Fig. S12b), indicating the size and morphology
of the self-assembled structure does not impact the final
properties of the CDs. Last but not the least, the amphiphilic
structure of TTC4L is important in the CDs formation. Control
experiments suggest that no CDs are formed when simply
disperse terthiophene (TT) in water with the same irradiation
condition. Although it is insoluble and forms ‘aggregates’, no
a
3x104
b
36.50 mW
46.50 mW
56.70 mW
66.50 mW
76.70 mW
86.50 mW
96.00 mW
106.50 mW
116.50 mW
126.50 mW
Slope=1.89
2x104
104
103
1x104
0
350 400 450 500 550 600 650
40
60
80 100 120140
Wavelength (nm)
Excitation Intensity / mW
Figure 3. a) Two photon spectra of TTC4L-CDs at different laser excitation
intensities of 730nm femtosecond pulse laser. b) Relationship between the
two-photon emission intensity and laser excitation intensity.
a
b
no light
0.01
0.00
-0.01
-0.02
with light
0 µs
obvious
fluorescence
enhancement
was
observed
1.0 µs
2.0 µs
3.0 µs
4.0 µs
5.0 µs
6.0 µs
7.0 µs
(Supplementary Fig. S12). It is possible that self-assembly
allows facile diffusion of oxygen into the terthiophene arrays
which triggers the carbonization of the TTC4L molecules.
simulated result
300
400
500
600
3480
3510
Field (G)
3540
Wavelength (nm)
O
COOH
S
Figure 4. a) Time-resolved transient spectra of TTC4L aqueous solution
under 355nm pump light. b) Electron paramagnetic resonance spectra of
TTC4L aqueous solution by adding BMPO as radical trap agent.
O
a
N
S
COOH
S
TTC8L
To gain more insight into the formation mechanism of
TTC4L-CDs, time-resolved transient absorption (TRTA)
spectroscopy was employed to study the intermediate species
generated in the photo-irradiation process. The characteristic
peak of terthiophene group at triplet state (3TTC4L*)36 locating
c 1600
1200
b
TTC4L
TTC8L
0.8
800
400
0
0.4
TTC4L
TTC8L
3
at 452 nm was observed (Fig. 4a). The lifetime of TTC4L* is
about 2.12 μs (Supplementary Fig. S8). This means that the
excited triplet TTC4L (3TTC4L*) may have sufficient lifetime to
transfer its energy to triplet oxygen to generate ROS. Indeed,
as the TTC4L aqueous solution was exposed to light, a typical
electron paramagnetic resonance (EPR) signal (Fig. 4b, red line),
was observed using BMPO as the radical trap. The simulated
0.0
200
300
400
500
600
700
0
5
10
15
20
25
Wavelength (nm)
Irradiation Time (h)
Figure 5. a) Chemical structure of TTC8L. b) UV-vis spectra of TTC4L
and TTC8L aqueous solution. c) Fluorescence intensity of TTC4L and
TTC8L aqueous solution with increase of light irradiation time,
respectively.
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17 S.-W. Hu, S. Qiao, B.-Y. Xu, X. Peng, J.-J. Xu and H.-Y. Chen, Anal.
In summary, we report in this work the first case of visible light
generated carbon dots in the molecular self-assembly of a
terthiophene amphiphile TTC4L. The resultant CDs display narrow
size distribution which endows the CDs with excitation-independent
emission and two-photon emission. The absolute fluorescence
quantum yield of these CDs can be as high as ca. 87% which is
probably owing to the presence of alkyl chains and COOH groups on
the surface as a result of the mild photoreaction condition.
Mechanism study shows that visible light irradiation facilitates the
formation of the long-lived TTC4L triplets, which transfer its energy
to oxygen to produce O2 . The reactive O2 radical triggers the
carbonization of the terthiophene skeleton in the self-assembly of
TTC4L. Although the details for the carbonization is still not clear,
we believe that the pre self-assembly of TTC4L is very crucial in the
CD formation since it allows the terthiophene groups arrange in
sufficient vicinity and order which allows facile generation of C-C
bonds. In a word, the present visible light driven strategy provides a
new method to prepared high quality CDs, which are promising for
myriad applications, such as solar energy conversion, bioimaging,
etc.
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Chem., 2017, 89, 2131-2137.
DOI: 10.1039/C7CC08876K
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This work is supported by the National Natural Science
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