Photocatalytic carbon dioxide reduction coupled with benzylamine oxidation over Zn-Bi2WO6microflowers

Article abstract of DOI:10.1039/d1gc00676b

Using solar energy to realize CO₂reduction and benzylamine oxidation is of great importance. Here, we design Zn-Bi₂WO₆microflowers catalyst, which can simultaneously reduce CO₂to CO and oxidize benzylamine toN-benzylbenzaldimine with high activities and selectivities in a simple photocatalytic system.

Full text of DOI:10.1039/d1gc00676b

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Photocatalytic carbon dioxide reduction coupled
with benzylamine oxidation over Zn-Bi2WO6
microflowers†
Cite this: Green Chem., 2021, 23,
2913
Received 21st February 2021,
Accepted 30th March 2021
Dongxing Tan,a,b Xiuyan Cheng,a,b Jianling Zhang,
*
a,b,c Yufei Sha,a,b
d
Xiaojun Shen,a,b Zhuizhui Su,a,b Buxing Han a,b,c and Lirong Zheng
DOI: 10.1039/d1gc00676b
rsc.li/greenchem
Using solar energy to realize CO2 reduction and benzylamine oxi- ate the reduction products of CO2 and oxygen.10,11 Second, the
dation is of great importance. Here, we design Zn-Bi2WO6 microfl- efficiency of CO2RR is usually low.12–16 As a result, it is still
owers catalyst, which can simultaneously reduce CO2 to CO and difficult to achieve the expected photocatalytic efficiency simply
oxidize benzylamine to N-benzylbenzaldimine with high activities by constructing the catalyst with a special structure. In light of
and selectivities in a simple photocatalytic system.
the role of sacrificial reagents (hole consumption) in photo-
catalytic CO2RR, a hole-consuming reaction can provide a sacri-
ficial reagent-free way, which can effectively capture the holes
generated in the photocatalytic process and make full use of the
photogenerated charges.17 Therefore, coupling photocatalytic
CO2RR with a hole-consuming reaction could overcome the
limitations of photocatalytic CO2RR and maximize photo-
catalytic efficiency and energy utilization.
Here, we demonstrate for the first time the combination of
photocatalytic CO2RR with benzylamine oxidation reaction,
which is a hole-consuming reaction and an important approach
to synthesize N-benzylbenzaldimine.18–20 For this strategy, CO2
consumes electrons to generate CO, while benzylamine con-
sumes holes to get N-benzylbenzaldimine. Therefore, neither
sacrificial agent nor additional oxidant (like oxygen) is needed.
The Zn-Bi2WO6 microflowers assembled by ultra-thin
nanosheets were synthesized as a photocatalyst, which can
improve the rapid separation and transfer of photoexcited elec-
trons and holes, so as to ensure that they can participate in the
simultaneous CO2RR and benzylamine oxidation reaction. The
maximum production rates of CO and N-benzylbenzaldimine
can reach 127.5 μmol g−1 h−1 and 13.1 mmol g−1 h−1, respect-
ively, which are both the highest among the reported values of
the separate CO2RR and benzylamine oxidation reaction under
comparable conditions. A scheme for the simultaneous photo-
catalytic CO2RR and benzylamine oxidation reaction by Zn-
Bi2WO6 microflowers is illustrated in Scheme 1.
Introduction
These days, photocatalytic carbon dioxide reduction reaction
(CO2RR) has been attracting tremendous attention because it
can mitigate the greenhouse effect, achieve the carbon cycle
and remit the energy crisis.1–5 To effectively convert CO2 into
carbon compounds (e.g., carbon monoxide, methane and
formic acid), a sacrificial agent like triethanolamine, sodium
sulfite or triethylamine is usually a requisite to capture photo-
excited holes, which is economically unfeasible and wasteful of
holes.4,6–9 The photocatalyst with special micro- and nano-struc-
ture can effectively promote the separation of the photocharge
and hole, so it can also have a certain photocatalytic efficiency
without the sacrificial agent.2 To date, great efforts have been
devoted to the development of photocatalytic CO2RR systems
without a sacrificial agent by constructing a catalyst with a
special structure, but are restricted mainly in terms of two main
issues. First, oxygen evolution reaction is inevitable in many
aqueous solution catalytic systems, causing extra steps to separ-
aBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid,
Interface and Chemical Thermodynamics, CAS Research/Education Center for
Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of
Sciences, Beijing 100190, P. R. China. E-mail: zhangjl@iccas.ac.cn
bSchool of Chemical Sciences, University of Chinese Academy of Sciences, Beijing
100190, P. R. China
cPhysical Science Laboratory, Huairou National Comprehensive Science Center,
Beijing 100190, P. R. China
dBeijng Synchrotron Radiation Facility (BSRF), Institute of High Energy Physics,
Chinese Academy of Sciences, Beijing 100049, P. R. China
Results and discussion
Synthesis and structural characterizations of Zn-Bi2WO6
microflowers
†Electronic supplementary information (ESI) available: SEM and TEM images,
XRD patterns, EXAFS spectra, XPS spectra and band structures. See DOI:
10.1039/d1gc00676b
The Zn-Bi2WO6 photocatalyst was synthesized by a solvo-
thermal strategy. As an example, Fig. 1 shows the characteriz-
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Fine structure of Zn-Bi2WO6 microflowers
The fine structure of Zn-Bi2WO6 was investigated by synchro-
tron extended X-ray absorption fine structure (EXAFS) spec-
troscopy. For X-ray absorption near-edge structure (XANES),
the pre-edge position of Zn-Bi2WO6 is located closer to that of
ZnO (Fig. 2a), suggesting that Zn exists in the form of (+2) oxi-
dation state in Zn-Bi2WO6. Fourier transform (FT) k3-weighted
χ(k) function of the EXAFS spectrum shows a dominant peak
at 1.49 Å, belonging to the coordination bond between Zn and
O in Bi2WO6 (Fig. 2b). Compared with ZnO and Zn foil, there
is no Zn−Zn coordination peak in Zn-Bi2WO6. These results
reveal that Zn exists in Zn-Bi2WO6 as isolated ions rather than
as Zn or ZnO particles. In Bi L3-edge XANES, the white line
intensity of Zn-Bi2WO6 is stronger compared with that of
Bi2WO6 (Fig. S3†). Meanwhile, in the FT k3-weighted χ(k) func-
tions of the EXAFS spectra, the intensity of Bi–O of Zn-Bi2WO6
is weaker than that of Bi2WO6. In W L3-edge XANES, the white
line intensity of Zn-Bi2WO6 is weakened compared with that of
Bi2WO6, and the intensity of W–O of Zn-Bi2WO6 is weaker than
that of Bi2WO6 in FT k3-weighted χ(k) function of the EXAFS
spectra. This indicates that Zn doping changes the local
atomic structure of Bi2WO6.11 X-ray photoelectron spectra
further prove that Zn exists as Zn2+ and Zn doping changes the
surface structure of Bi2WO6 (Fig. S4†), which is consistent with
the EXAFS results.22 Since the radius of Zn2+ (74 pm) is closer
to that of W6+ (62 pm) than of Bi3+ (103 pm), it is expected that
Zn2+ ions could replace partially the W6+ ions, forming Zn2+
substitutionally doped Bi2WO6.23–25 The Zn2+ ions can act as
electron traps to promote the electron–hole separation and
enhance the photocatalytic efficiency.
Scheme 1 Illustration of simultaneous photocatalytic CO2RR and
4-methylbenzylamine oxidation reaction by Zn-Bi2WO6 microflowers.
Fig. 1 (a–c) SEM images of Zn-Bi2WO6. (d) TEM image of Zn-Bi2WO6.
(e) HRTEM image and SAED pattern (inset) of Zn-Bi2WO6. (f) AFM image
of Zn-Bi2WO6. (g) EDX mappings of Zn-Bi2WO6. Scale bars: 3 µm (a),
500 nm (b), 200 nm (c), 50 nm (d), 3 nm (e), 50 nm (f) and 500 nm (g).
Photochemical performance of Zn-Bi2WO6 microflowers
The performance of Zn-Bi2WO6 for the simultaneous photo-
catalytic CO2RR and 4-methylbenzylamine oxidation reaction
was studied. The reaction was irradiated by simulated solar
light irradiation at atmospheric pressure and room tempera-
ture. No sacrificial agent or additional oxidant (like oxygen)
was added. After the reaction, the gas and liquid products
were analyzed by gas chromatograph and 1H nuclear magnetic
resonance spectroscopy, respectively. The results show the for-
mation of CO and (E)-N-(4-methylbenzyl)-1-(p-tolyl)methani-
mine (Fig. S5†), and no other products were detected. Fig. 3a
ations of the Zn-Bi2WO6 with Zn content of 1.0 wt%, deter-
mined by inductively coupled plasma-mass spectrometry.
From scanning electron microscopy (SEM) and transmission
electron microscopy (TEM) images, the product has a flower-
like microstructure, which is assembled by nanosheets in a
lateral size of ∼50 nm (Fig. 1a–d). The high-resolution TEM
(HRTEM) image shows the lattice fringes with a distance of
0.32 nm corresponding to the (131) crystal plane of russellite
Bi2WO6 (Fig. 1e).21 Powder X-ray diffraction (XRD) analysis
further confirms the formation of russellite Bi2WO6 (JCPDS
card no. 39-0256), which is consistent with the selected area
electron diffraction (SAED) pattern (inset in Fig. 1e). It is
obvious that Zn doping does not change the crystal confor-
mation of Bi2WO6 (Fig. S1†). The atomic force microscopy
(AFM) image reveals that the average thickness of nanosheets
is 4.9 nm (Fig. 1f). Elemental mappings reveal the even distri-
bution of Bi, W, O, and Zn (Fig. 1g). For comparison, Bi2WO6
was synthesized in the absence of zinc nitrate hexahydrate,
while the other experimental conditions were the same as
those for Zn-Bi2WO6. Its XRD pattern and morphology (Fig. S1
and S2†) are similar to those of Zn-Bi2WO6.
Fig. 2 (a) Zn K-edge XANES spectra of Zn-Bi2WO6. (b) Fourier trans-
form (FT) k3-weighted χ(k) function of the EXAFS spectra of Zn-Bi2WO6.
ZnO and Zn foil were used as contrast samples.
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that the photogenerated holes cannot be effectively consumed
during a single photocatalytic CO2RR, so the electrons and
holes may recombine in the process of migration to the Zn-
Bi2WO6 surface to reduce the number of electrons involved in
CO2RR. However, when the photocatalytic CO2RR and
4-methylbenzylamine oxidation reaction simultaneously
proceed, the photogenerated holes can be consumed by the
benzylamine oxidation reaction, thus improving the reduction
efficiency of CO2. Third, the single 4-methylbenzylamine oxi-
dation reaction catalyzed by Zn-Bi2WO6 was tested under a
nitrogen (N2) atmosphere, which shows a low production rate
of (E)-N-(4-methylbenzyl)-1-(p-tolyl)methanimine of 0.7 mmol
g−1 h−1 (D in Fig. 3b). Fourth, the photocatalytic CO2RR and
4-methylbenzylamine oxidation reaction catalyzed by Zn-
Bi2WO6 were performed without light irradiation. Neither CO
Fig. 3 (a) Time-dependent CO and (E)-N-(4-methylbenzyl)-1-(p-tolyl)
methanimine production amounts by Zn-Bi2WO6. (b) Photocatalytic
CO2RR and 4-methylbenzylamine oxidation reaction under various con-
ditions. (c) Stability of Zn-Bi2WO6 for five cycles. (d) Photocatalytic
CO2RR and diverse para-substituted benzylamine oxidation activities of
Zn-Bi2WO6.
nor
(E)-N-(4-methylbenzyl)-1-(p-tolyl)methanimine
was
detected (E in Fig. 3b). Obviously, the efficiency of the simul-
taneous photocatalytic CO2RR and 4-methylbenzylamine oxi-
dation reaction is much higher than of the two single reac-
tions. In a photocatalytic reaction, CO2RR consumes electrons,
while benzylamine oxidation reaction consumes holes.
Consequently, the recombination of photogenerated electrons
shows that CO and (E)-N-(4-methylbenzyl)-1-(p-tolyl)methani- and holes is effectively reduced, making them more likely to
mine production amounts increase linearly with reaction time migrate to the surface of the Zn-Bi2WO6 to participate in
during a 10 h test. It indicates the good stability of the Zn- reduction and oxidation reactions. From the above results, it
Bi2WO6 photocatalyst for the duration of the photocatalytic can be concluded that there is a synergistic effect for CO2RR
reaction process. The production rates of CO and (E)-N-(4- and 4-methylbenzylamine oxidation reaction during the coup-
methylbenzyl)-1-(p-tolyl)methanimine are 127.5 μmol g−1 h−1 ling process, which can promote each other efficiently.
and 13.1 mmol g−1 h−1 (with >99% selectivity), respectively.
To evaluate the stability of Zn-Bi2WO6, the performances of
CO2 and water could act as amine activating agents to favor the photocatalytic coupling reaction for five cycles were
and accelerate the photocatalytic oxidative coupling of benzyl- measured. The production rates of CO and (E)-N-(4-methyl-
amines,26 thus leading to a difference in oxidation efficiency benzyl)-1-(p-tolyl)methanimine are basically stable and no
and reduction efficiency. For comparison, the simultaneous drop was detected during the five cycles (Fig. 3c). The mor-
photocatalytic CO2RR and 4-methylbenzylamine oxidation phology of the used Zn-Bi2WO6 is the same as that of the pris-
reaction was also studied using Bi2WO6 as a catalyst. The pro- tine Zn-Bi2WO6 (Fig. S7†). Besides, the crystallinity of Zn-
duction rates of CO and (E)-N-(4-methylbenzyl)-1-(p-tolyl) Bi2WO6 is well maintained after five photocatalytic runs
methanimine are 42.4 μmol g−1 h−1 and 5.1 mmol g−1 h−1
respectively, which are much lower than those catalyzed by Zn-
,
(Fig. S8†).
The photocatalytic CO2RR integrated with diverse para-sub-
Bi2WO6. It indicates that the introduction of Zn2+ into Bi2WO6 stituted benzylamine oxidation reaction (R = –OCH3, –H, –Cl,
can effectively improve the photocatalytic efficiency. Moreover, –OCF3) by Zn-Bi2WO6 was further investigated. The results
the production rates of CO and (E)-N-(4-methylbenzyl)-1-(p- show that CO2 and benzylamines can be transformed simul-
tolyl)methanimine from the coupled reaction catalyzed by Zn- taneously
to
CO
and
the
corresponding
Bi2WO6 are higher than those of the reported single reactions N-benzylbenzaldimines (with >99% selectivity) effectively. For
under comparable conditions (ESI Table S1,† 11,27–30 the four different para-substituents, the production rates of CO
Table S2† 20,31–34).
and N-benzylbenzaldimine determined at 4 h are above
Some control experiments for the simultaneous photo- 90 μmol g−1 h−1 and 9 mmol g−1 h−1, respectively (Fig. 3d).
catalytic CO2RR and 4-methylbenzylamine oxidation reaction The difference in performances of the coupling reactions can
catalyzed by Zn-Bi2WO6 were tested under different photo- be attributed to the electron supplying ability of the substitu-
catalytic conditions (Fig. 3b). For all these control experiments, ent. The electron donating groups (R = –CH3, –OCH3) could
no sacrificial agent or additional oxidant (like oxygen) was increase the electron density than the electron withdrawing
added. First, when CO2 was replaced by air, nearly no CO was groups (R = –Cl, –OCF3), thus promoting the efficiency of the
detected and the production rate of (E)-N-(4-methylbenzyl)-1- coupling reaction.19
(p-tolyl)methanimine was 11.1 mmol g−1 h−1 (B in Fig. 3b and
Moreover, a series of Zn-Bi2WO6 catalysts with different Zn
Fig. S6†). Second, the single photocatalytic CO2RR catalyzed by contents were synthesized. All of them present the russellite
Zn-Bi2WO6 was studied. The CO production rate was as low as Bi2WO6 crystal structure and flower-like morphologies
6.7 μmol g−1 h−1 (C in Fig. 3b). It can be attributed to the fact (Fig. S9–S12†), similar to the above Zn-Bi2WO6 with Zn content
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of 1.0 wt%. Their performances for the simultaneous photo- sufficiently enough reductive and oxidative potentials to
catalytic CO2RR and 4-methylbenzylamine oxidation reaction CO2RR and benzylamine oxidation (Fig. S13†). The transient
were studied. Using Zn-Bi2WO6 catalysts with Zn contents of state photoluminescence (PL) spectra of Zn-Bi2WO6 were
0.4, 1.0, 1.8 and 2.3 wt%, the CO production rates determined measured to evaluate the separation efficiency of photoexcited
at 4 h are 80.6, 127.5, 110.2 and 94.2 μmol g−1 h−1, while the electrons and holes (Fig. 4c). The average lifetime of Zn-
N-benzylbenzaldimine production rates are 10.6, 13.1, 11.7 Bi2WO6 is 3.93 ns, which is longer than that of Bi2WO6 (2.50
and 10.1 mmol g−1 h−1, respectively. It is obvious that with the ns). The prolonged charge lifetime in Zn-Bi2WO6 indicates that
increase of Zn doping in Bi2WO6, the catalytic performance the photocarrier can migrate to the surface of the catalyst to
increases first and then decreases. The optimum Zn content in participate in the subsequent CO2RR and benzylamine oxi-
Bi2WO6 is 1.0 wt% to get the maximum efficiency for the coup- dation reaction, thus improving photocatalytic performance.
ling reaction.
In addition, the PL intensity of Zn-Bi2WO6 in steady state PL
spectra is lower than that of Bi2WO6 (Fig. 4d), indicating the
effectively restrained recombination of photoexcited electron–
hole pairs by Zn-Bi2WO6.36,37
Photoelectric properties of Zn-Bi2WO6 microflowers
The above results reveal the high efficiency of coupled photo-
catalytic CO2RR and benzylamine oxidation reaction catalyzed
by Zn-Bi2WO6. To get the information on the underlying
mechanism, the photoelectric properties of the photocatalyst
were investigated. For UV-vis absorption spectra, Zn-Bi2WO6
exhibits a slight red shift of the absorption edge as compared
with Bi2WO6, indicating the enhanced light absorption and
reduced band gap (Fig. 4a). The calculated optical band gaps
of Zn-Bi2WO6 and Bi2WO6 are 3.19 and 3.24 eV, respectively.35
The conduction band (CB) positions of Zn-Bi2WO6 and
Bi2WO6 were determined by Mott−Schottky plots to be −0.85 V
and −0.78 V (V vs. Ag/AgCl, pH = 6.8), respectively (Fig. 4b).
The proper band structure manifests that Zn-Bi2WO6 possesses
The transient photocurrent spectra and electrochemical
impedance spectra were examined to further reveal the charge
separation and transport efficiency of Zn-Bi2WO6. Zn-Bi2WO6
exhibits rapid and uniform photocurrent responses under
cycling light on and off, which is significantly higher than that
of Bi2WO6 (Fig. 4e). It indicates that the separation of photo-
excited electrons and holes is greatly enhanced in Zn-
Bi2WO6.38,39 Moreover, Zn-Bi2WO6 shows a much smaller arc
radius in Nyquist plots than Bi2WO6 (Fig. 4f), suggesting its
lower charge transfer resistance.4,40 The above analysis shows
that the introduction of Zn2+ into Bi2WO6 can promote the
separation and transfer of photogenerated electrons and holes,
and effectively improve the photocatalytic redox efficiency.
Furthermore, the CO2 adsorption properties of Zn-Bi2WO6
and Bi2WO6 catalysts were measured (Fig. S14†). Obviously, the
Zn-Bi2WO6 catalyst presents improved CO2 adsorption capacity
than Bi2WO6. For example, the CO2 adsorption capacity of Zn-
Bi2WO6 reaches 4.6 mg g−1 at 298 K and 1 atm. Also, the CO2
adsorption properties of Zn-Bi2WO6 and Bi2WO6 catalysts were
further explored via CO2 temperature-programmed desorption
(CO2-TPD) profiles. Peaks at the temperature of 90 °C were
observed in the CO2-TPD profile, indicating the weak CO2
adsorption of the catalysts. The peaks beyond 250 °C corres-
pond to strong CO2 adsorption. It is obvious that the peak of
CO2 desorption for Zn-Bi2WO6 moves to a higher temperature
than that of Bi2WO6, which indicates that Zn2+ doping enhances
the chemical adsorption of CO2 for the catalyst.41
Conclusions
In conclusion, we prepared Zn-Bi2WO6 microflowers as a
photocatalyst for coupled CO2RR and benzylamine oxidation
reaction in the absence of a sacrificial agent or oxidant. The
Zn2+ ions embedded in Bi2WO6 can be used as electron traps
to improve the separation efficiency of the photoexcited elec-
trons and holes, thus prolonging charge lifespan. The activi-
ties and selectivities of both CO2 reduction to CO and benzyla-
mine oxidation to N-benzylbenzaldimine are improved in such
a simple photocatalytic system. It is anticipated that the photo-
catalytic CO2RR will be coupled with other different types of
oxidation reactions for improving efficiencies in future.
Fig. 4 (a) UV-vis absorption spectra and (inset) corresponding band
gap energies of Zn-Bi2WO6 and Bi2WO6. (b) Mott–Schottky plots, (c)
transient state, (d) steady state photoluminescence spectra, (e) transient
photocurrent spectra and (f) electrochemical impedance spectra of Zn-
Bi2WO6 and Bi2WO6.
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Conflicts of interest
There are no conflicts to declare.
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Acknowledgements
We acknowledge the financial support from the Ministry of
Science and Technology of China (2017YFA0403003), National
Natural Science Foundation of China (22033009) and Beijing
Municipal
Science
&
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