Quinacridone-pyridine dicarboxylic acid based donor-acceptor supramolecular nanobelts for significantly enhanced photocatalytic hydrogen production

Article abstract of DOI:10.1039/c9tc04175c

The self-assembled nanobelt photocatalysts (SQAP-C4 and SQAP-C8) with quinacridone containing butyl and octyl side chains as electron donors and pyridine dicarboxylic acid as an acceptor were firstly developed for efficient hydrogen evolution. SQAP-C4 without the loading of cocatalyst Pt exhibited a superior H₂ evolution reaction rate of 656 μmol h^-1 g^-1 and excellent stability.

Full text of DOI:10.1039/c9tc04175c

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Nosang V. Myung, Yong-Ho Choa et al.
A
noble gas sensor platform: linear dense assemblies of
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J Po lue ran sael od fo Mn aot te rai ad l jsu Cs ht emm ai rs gt ri yn sC
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DOI: 10.1039/C9TC04175C
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Quinacridone-pyridine dicarboxylic acid based donor-acceptor
supramolecular nanobelts for significantly enhanced
photocatalytic hydrogen production
Received 00th January 20xx,
Accepted 00th January 20xx
a
a
a
b
a
a
Mengyu Xu , Kangyi Kong , Haoran Ding , Yanmeng Chu , Shicong Zhang , Fengtao Yu , Haonan
DOI: 10.1039/x0xx00000x
a
b
*a
Ye , Yue Hu and Jianli Hua
The self-assembled nanobelt photocatalysts (SQAP-C4 and SQAP- in the photocatalytic water splitting. Interestingly, pyridine-2,6-
C8) with quinacridone containing butyl and octyl side chains as dicarboxylic acid (PDA) with two carboxylic acid groups exhibits
1
8
electron donor and pyridine dicarboxylic acid as acceptor were pretty hydrophilic. What’s more, the pyridine ring with an
firstly developed for efficient hydrogen evolution. SQAP-C4 without electron-deficient structure (an electron acceptor) can form a
built-in diploe combined with QA (an electron donor) by donor-
2
the loading of cocatalyst Pt exhibited superior H evolution reaction
of 656 μmol h g and excellent stability.
1
4, 19,20
-1
-1
acceptor (D-A) interaction.
Due to D-A effect, the charge
2
0-22
separation efficiency is improved.
Based on above analysis,
two D-A QA-based supramolecular catalysts (SQAP-C4 and
SQAP-C8) with different length of butyl and octyl chains have
been successfully synthesized and used for hydrogen evolution.
Furthermore, the different length of alkyl chains may affect the
supramolecular packing which further has an influence on
photocatalytic activity.
With the advent of the energy crisis, hydrogen has become a
potential energy source that can alleviate the energy crisis.
Interestingly, the natural light synthesis system can convert
sunlight into hydrogen energy by integrating the π-π conjugate
1
, 2
chromophore and active catalytic center. Therefore, organic
synthetic materials containing π-π chromophores may have
3
It is the first time that the self-assembled quinacridone
derivative is used for hydrogen evolution. Surprisingly, the two
certain advantages in artificial photosynthetic systems. Small
organic molecules containing π-π chromophores have been
supramolecular photocatalysts can achieve
a gratifying
used in organic optoelectronic materials as well as in solid state
semiconductors.4-5 While the self-assembled systems with large
electron delocalization are reported, which are applied in
hydrogen evolution reaction (HER) without loading the
-
cocatalyst Pt, in which SQAP-C4 exhibits HER of ca. 656 μmol h
1
-1
6
,7
g . In addition, the photocatalytic activity of SQAP-C4 with Pt
cocatalyst loaded was also observed, which is about 3 times
1.93 mmol h g ) higher than SQAP-C4 without Pt. Moreover,
charge transport materials and water splitting.
Quinacridone (QA) and its derivatives, as well-known red-
violet dyes with large π-π chromophore, have many excellent
advantages such as chemical stability, good carrier mobility,
thermal stability and wide ultraviolet-visible absorption
-1 -1
(
the supramolecular photocatalysts show excellent stability and
the photocatalytic performance is not decayed after 15 hours of
illumination. Hence, two new QA-PDA self-assembled nanobelt
11- photocatalysts provide a new idea for the design of organic
range.8 Therefore, it is widely used in various optoelectronic
,9
1
0
devices, including organic solar cells, light-emitting diodes,
1
3
14-16
photocatalysts.
and field effect transistors.
It is important to note that in
The synthetic route of two QA-PDA with butyl and octyl
chain(termed as QAP-C4 and QAP-C8) is shown in Scheme S1.
And the self-assembled SQAP-C4 and SQAP-C8 nanobelts were
most studies, quinacridone derivatives are primarily used as
1
0
17
charge transport materials or photosensitizers. Neverthless,
the problems of fast charge recombination and hydrophobic
resulting from strong rigidity limit the application of QA system
synthesized through
a facile and economic acid-base
neutralization reaction method by using triethanolamine (TEOA)
as base and HCl as acid. The process is schematically illustrated
in Scheme 1.
The scanning electron microscopy (SEM) and transmission
electron microscopy (TEM) can be used to determine how alkyl
chain variations altered supramolucles morphologies and
molecular packing. As shown in SEM images (Fig. 2a~2b), the
a
Key Laboratory for Advanced Materials, Institute of Fine Chemicals, School of
Chemistry and Molecular Engineering, East China University of Science and
Technology, 130 Meilong Road, Shanghai, 200237, PR China.
Email: jlhua@ecust.edu.cn
b
Michael Grätzel Center for Mesoscopic Solar Cells, Wuhan National Laboratory
for Optoelectronics, Huazhong University of Science and Technology, Wuhan
4
30074, Hubei, PR China.
Electronic Supplementary Information (ESI) available: [details of any supplementary self-assembled supramolecules of SQAP-C4 and SQAP-C8 were
information available should be included here]. See DOI: 10.1039/x0xx00000x
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DOI: 10.1039/C9TC04175C
Scheme 1. Schematic illustration of formation of the self-assembled SQAP-C4
nanostructures
nanoribbon formed by π-π stacking and hydrogen bond, in
which SQAP-C4 showed shorter nanoribbon compared with
SQAP-C8. TEM images revealed that SQAP-C4 assembled into a
thin and narrow nanobelt like willow leaves with a width of
Fig. 2 SEM images of SQAP-C4 (a) and SQAP-C8 (b); TEM images of SQAP-C4 (c)
about 50 nm and a length of hundreds of nanometers (Fig. 2c and SQAP-C8 (d).
~
2d). In contrast, SQAP-C8 formed exclusively wide and long
The Raman spectra were performed to further determine the
nanobelts, which was hundreds of nanometers to micrometers
in length and about 100 nm in width. The one possible
explanation may be that the steric hindrance of the octyl chains
prevented closer π-π stacking and probably contributed to the
formation of J-aggregation.
It is well known that thin layer structure is a favorable
parameter for photocatalytic performance because it can
π-π interaction between the supramolecules (Fig. 3b).
2
9
-
According to previous research, the peak of 1602 cm
1
corresponds to the in-plane C=C/C-C stretching/shrinking of
the quinacridone aromatic ring core coupled to the C=O
antisymmetric stretching, which was sensitive to the π-π
2
3
-1
stacking effect. However, the peak at 1359 cm attributed to C-
4, 25 H in plane bending was not sensitive to intermolecular
2
provide more react sites and shorter diffusion distance.
What’s more, the shorter distance to the surface facilitates the
-1
-1
interactions. Thus, the ratio of 1602 cm /1359 cm Raman
intensity can be used as an effective marker to evaluate the π-
π interaction. The ratio of SQAP-C4 (1.35) and SQAP-C8 (1.34)
was higher than the QAP-C4 (1.17) and QAP-C8 (1.17)
respectively, which revealed the improvement of π-π
interaction between the suparmolecules. Thus, there is better
regularity in suparmolecules and it can form fast-transporting
channels in the π–π stacking direction and the carriers can be
transported by the channels.
3
migration of photogenerated carriers. From the AFM image
Fig. S1 and Fig. S2), we can observe that the self-assembled
(
SQAP-C4 crystalized well with a thinner thickness of 37 nm,
while the layer thickness of supramolecule SQAP-C8 was 55 nm.
Hereby, the supramolecule morphologies clearly changed by
only varying the alkyl chain length of QA moiety and SQAP-C4
showed a thinner and narrow nanobelt structure which may be
beneficial to photocatalysis.
Absorbance spectra of the monomers QAP-C4 and QAP-C8
were measured in DMSO (Fig. S3 and Fig. S4) and the optical
properties of QAP-C4, QAP-C8, SQAP-C4 and SQAP-C8 were
The X-ray diffraction (XRD) measurement was used to further
evaluate the π-π interaction within the supramolecules. A
slightly wide peak around 25°in QAP-C4 and QAP-C8 can be
seen, indicating a certain degree of π-π interaction in the
precursors (Fig.S7-S8). As for supramolecules, it can be seen
that SQAP-C4 showed a peak at 2θ = 25.40°which corresponds
to the layer-to-layer spacing (d-spacing of π-π stacking) of 3.5
1
4
Å. In addition, the peaks of 2θ = 31.64° and 2θ = 45.42° with
d-spacing of 2.82 Å and 1.99 Å indicated the possible formation
2
6
of hydrogen-bond, respectively. As for the self- assembled
SQAP-C8, it only showed one peak at 2θ = 25.30°corresponded
to 3.52 Å which could be assigned to further π-π stacking
distance.14 This may be due to the longer octyl chain will wrap
around chromophore hindering the formation of hydrogen
3
bond and leading to further π-π stacking distance. And the
result revealed that the SQAP-C4 self-assemble tighter and has
improved regularity from π-π stacking interaction and hydrogen
bond formation resulting from the shorter length of butyl chain.
The smaller d-spacing of π-π stacking in the SQAP-C4 nanobelts
also meant a higher electron cloud overlap density which is Fig. 3 (a) XRD patterns of SQAP-C4 and SQAP-C8 powder. (b) Raman spectra of
QAP-C4, QAP-C8, SQAP-C4 and SQAP-C8 powder. (c) UV–vis diffuse reflection
3
, 27, 28
expected to benefit the migration of charge carriers.
spectra of QAP-C4, QAP-C8, SQAP-C4 and SQAP-C8 (Inset: the corresponding
colors and the Tauc plots.) (d) Band diagram for SQAP-C4 and SQAP-C8.
2
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measured by UV-vis diffuse reflection spectra (DRS) (Fig.3c).
Firstly, owing to the π-π stacking, the electronic clouds
overlapped and isolated molecule energy level was linear
combined to the semiconductor energy band which presented
an absorption edge of 650 nm, indicating their excellent ability
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DOI: 10.1039/C9TC04175C
3
0
of response to visible light. Secondly, the absorption peaks of
monomers QAP-C4 and QAP-C8 in DMSO are almost coincident.
However, there is an obvious red-shifted in the DRS spectrum
of SQAP-C4 compared with SQAP-C8, which resulted from more
3
1
closely π-π stacking of SQAP-C4. What’s more, the red-shifted
of SQAP-C4 revealed broader spectrum absorption region.
Thirdly, with the contents of water increased, the monomer
molecules began to aggregate, and the red shift of the
absorption peak may indicate J-aggregation between
3
,32
supramolucles (Fig. S3 and Fig. S4). Finally, compared with 3a
and 3b, PQA-C4 and PQA-C8 have a new absorption peak
between 350 and 450 nm, respectively. This result indicated the Fig. 4 (a)Time-dependent photocatalytic hydrogen evolution over SQAP-C4 and
SQAP-C8. (b) The reaction rate comparison of SQAP-C4, SQAP-C8, Pt-loaded
effect of intramolecular charge transfer between the QA SQAP-C4 and Pt-loaded SQAP-C8. (c) Photostability for hydrogen evolution of the
SQAP-C4 and SQAP-C8. Reaction conditions: 50 mL water, 3 g AA, 30 mg
skeleton and the PDA group, which further proved the D-A photocatalyst under visible-light (400 nm < λ< 780 nm). (d) Proposed electron
2
transfer mechanism of supramolecular SQAP-C4 for photocatalytic H production.
interaction.10 What’s more, as shown in Table S2, the
theoretical calculation results showed SQAP-C4 has a larger
dipole moment of 0.67 Debye which proved a better ability of
charge separation.
According to the Tauc plots (Fig.3c, inset), the band gap
energy of the SQAP-C4 and SQAP-C8 was calculated to be 1.76
eV and 1.94 eV, respectively. According to the calculation result,
the HOMO of SQAP-C4 and SQAP-C8 was measured to be -5.30
eV and -5.44 eV (vs vacuum), respectively. As a result, the LUMO
of SQAP-C4 and SQAP-C8 should be -3.54 eV and –3.50 eV from
The excellent performance can be attributed to the fact SQPA-
C4 has wider spectrum and more efficient photoinduced charge
separation resulting from the closer π-π stacking distance and
larger dipole moment. In addition to the photocatalytic
properties, the stability of SQAP-C4 and SQAP-C8 was also
evaluated in three consecutive runs of accumulatively 15 h with
intermittent evacuation every 5 h under visible light irradiation
2
(Fig. 4b). There was no noticeable attenuation in H production
rate after 3 cycling tests, suggesting the high stability of SQAP-
C4 and SQAP-C8. The stabilities of catalysts were further
verified by XRD, FT-IR and Raman data (Fig.S16-S18). In addition,
we also measured the hydrogen production of SQAP-C4 with
E
HOMO + Eg (Fig. 3d). Because the LUMO of supramolecules was
+
higher than that of H /H
enough reducing capacity to react with H producing H
2
(-4.5 eV), the supramolecules have
+
2
on the
surface of photocatalyst.
To further confirm the structure of SQAP-C4 and SQAP-C8,
-1
-1
1
wt% Pt. which reached 1933 μmol g h . From TEM image (Fig.
S14), we can observe that Pt particle was distributed on the
surface of SQAP-C4 uniformly. And it was 2.95 times more than
that of SQAP-C4 without Pt. While the SQAP-C8 with 1wt% Pt
the Fourier transform infrared (FT-IR) was carried out (Fig. S5
-1
and Fig. S6). The peak of 6a and 6b at 1743 cm was attributed
to the C=O stretching vibration of pyridine dicarboxylic ester
group. And this peak disappeared in QAP-C4 and QAP-C8,
indicating that the ester groups were all hydrolyzed to carboxyl
1
-1
(
317 μmol g- h ) was only 1.79 times than that of SQAP-C8
without Pt (Fig. 4c). The performances were compared with the
self-assembled materials recently reported (Table S3 in the
Supporting Information). In most of the studies already
reported, a cocatalyst is needed to reduce the overpotential,
but the introduction of a cocatalyst results in a large
consumption of precious metals. It should be noted that the
-
1
-1
-1
groups. And the peak of 1720 cm , 1724 cm , 1725 cm , 1726
-1
cm were attributed to the C=O stretching vibration of
quinacridone core. A series of peaks ranged from 1270 cm to
292 cm were attributed to the C-N stretching vibration of the
quinacridone core. And the peaks ranged from 1625 cm to
633 cm-1 were assigned to the characteristic stretching
-1
-1
1
-1
−1
-1
HER of 656 μmol h
g for SQAP-C4 without the loading of
1
cocatalyst Pt is comparable to or even higher than that of most
reported self-assembled photocatalysts shown in Table S4.
vibration of C=N of pyridine. Interestingly, it can be clearly seen
from Table S1 that the vibration peaks of self-assembled SQAP-
C4 and SQAP-C8 shifted to a higher wave numbers compared to
the monomer of QAP-C4 and QAP-C8, which further proved the
increase of the π-π conjugated structure in supramolecules of
Thus, the SQAP-C4 provides
a
resource-saving and
environmental friendly photocatalyst.
In order to further explore the electron transfer kinetics of
supramolecules, photoluminescence (PL) spectroscopy test was
conducted. As shown in Fig. S11, SQAP-C8 showed a strong
emission peak at 649 nm, indicating the fast recombination of
photogenerated carriers. In contrast, SQAP-C4 exhibited lower
fluorescence intensity with an emission peak at 652 nm. The
lower fluorescence intensity revealed superior charge
separation ability of SQAP-C4. The transient photocurrent
3
3
SQAP-C4 and SQAP-C8.
Their photocatalytic H
tested under visible light irradiation in L-ascorbic acid (AA)
aqueous solution as sacrificial agents (Fig. 4a, Fig.S15). The H
2
production without cocatalysts was
2
-1
-1
production rate were 394, 35.6, 656, 177 μmol g h (λ > 400
nm) for QAP-C4, QAP-C8, SQAP-C4 and SQAP-C8, respectively,
in which SQAP-C4 was 3.7 times higher than that of SQAP-C8.
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responses (I–t) was further performed and confirmed that
SQAP-C4 had promoted photoresponsive ability and photo-
generated carrier separation ability compared with SQAP-C8.
Fig. S10 illustrated the results of electrochemical impedance
spectroscopic (EIS) measurements. In general, smaller charge
transfer resistance, the faster interfacial electron transfer. Thus
SQAP-C4 had better photocatalyst capability.
Based on above experimental results, a possible mechanism
of hydrogen production by supramolecular is proposed. Take
SQAP-C4 as an example as shown in Fig. 4(d), photogenerated
carriers can be generated under visible-light irradiation, and
carriers are separated under the built-in electric field resulting
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-1
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with a hydrogen evolution rate of 656 μmol g h without any
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-1
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| J. Name., 2012, 00, 1-3
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J Po lue ran sael od fo Mn aot te rai ad l jsu Cs ht emm ai rs gt ri yn sC
Journal Name
COMMUNICATION
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3. H. F. Ji, R. Majithia, X. Yang, X. Xu and K. More, J. Am. Chem.
Soc., 2008, 130, 1005610057.
View Article Online
DOI: 10.1039/C9TC04175C
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J. Name., 2013, 00, 1-3 | 5
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Journal of Materials Chemistry C
Page 6 of 6
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DOI: 10.1039/C9TC04175C
Graphical Abstract
Quinacridone-pyridine dicarboxylic acid
based donor-acceptor supramolecular
nanobelts for significantly enhanced
photocatalytic hydrogen production
Mengyu Xu, Kangyi Kong, Haoran Ding, Yanmeng Chu, Shicong
Zhang, Fengtao Yu, Haonan Ye, Yue Hu and JianLi Hua*
In this paper, The self-assembled nanobelt photocatalysts
(SQAP-C4 and SQAP-C8) with quinacridone containing butyl
and octyl side chains as electron donor and pyridine dicarboxylic
acid as acceptor were firstly developed for efficient hydrogen
evolution. SQAP-C4 without the loading of cocatalyst Pt
-1 -1
exhibited superior H
2
evolution reaction of 656 μmol h g and
excellent stability.