Chinese Chemical Letters 33 (2022) 3733–3738

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Chinese Chemical Letters

journal homepage: www.elsevier.com/locate/cclet

Extending aromatic acids on TiO2 for cooperative photocatalysis with

triethylamine: Violet light-induced selective aerobic oxidation of
sulfides
Hui Li, Xia Li, Jun Zhou, Wenlong Sheng, Xianjun Lang∗
Sauvage Center for Molecular Sciences, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China

a r t i c l e i n f o a b s t r a c t

Article history: Designing visible light photocatalysts with a metal oxide semiconductor as the starting material could
Received 29 August 2021 expand a new horizon for the conversion and storage of solar energy. Here, the benchmark photocatalyst
Revised 12 September 2021
TiO2 was used to pursue this goal by anchoring aromatic acids. Extending the aromatic acid was strate-
Accepted 22 October 2021
gically deployed to design TiO2 complexes with violet light-induced selective aerobic oxidation of sulfide
Available online 29 October 2021
as the probe reaction. With benzoic acid (BA) as the initial molecule, horizontally extending one or two
Keywords: benzene rings furnishes 2-naphthoic acid (2-NA) and 2-anthracene acid (2-AA). Moreover, triethylamine
Aromatic acid (TEA), an electron transfer mediator, was introduced to maintain the integrity of the anchored aromatic
Extending π -conjugation acids. Notably, there was a direct correlation between the π -conjugation of aromatic acid ligand and
Complex photocatalyst the selective aerobic oxidation of sulfides. Among the three aromatic acids, 2-AA delivered the best re-
Oxidation of sulfides sult over TiO2 due to the most extensive π -conjugated system. Ultimately, violet light-induced selective
Cooperative photocatalysis
aerobic oxidation of sulfides into corresponding sulfoxides was conveniently realized by cooperative pho-
tocatalysis of 2-AA-TiO2 with 10 mol% of TEA. This work affords an extending strategy for designing the
next-generation ligands for semiconductors to expand visible light-induced selective reactions.
© 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia
Medica, Chinese Academy of Medical Sciences.

The development of solar energy conversion and storage is es-
sential for alleviating the looming energy and environmental cri-
sis triggered by the global population explosion and unprecedented
economic growth [1–4]. However, the intermittent and diffuse na-
ture of solar energy leave ample space to further developments.
Increasingly, semiconductor photocatalysis can expand a new hori-
zon for harnessing solar energy [5,6]. Whereas visible light utiliza-
tion rate in the solar spectrum still imposes restrictions on the
available scope of transition metal oxides on Earth [7,8]. For in-
stance, TiO2 can only absorb approximately 5% of natural sunlight
owing to its wide bandgaps (3.0 eV for rutile, 3.2 eV for anatase)
[9,10]. Nevertheless, TiO2 turns out to be a stepping stone to new
photocatalysts that close the energy gap [11,12].
Particularly, surface-modified TiO2 with carboxyl, hydroxyl con-
taining ligands such as ethylenediaminetetraacetic acid [13,14], sal-
icylic acid [15,16], catechol [17,18], glucose [19,20], and cyclodex-
trin [21,22] have aroused great interest on account of their high
absorption of visible light and low recombination of electron-hole
∗
Corresponding author.
E-mail address: xianjunlang@whu.edu.cn (X. Lang).
to achieve photocatalytic reactions efficiently. Besides, the proper-
ties of the TiO2 complexes, such as photochemical stability, opti-
cal response, and binding mode, are closely associated with the
structure of ligands [23–25]. Generally, aromatic organic acids con-
taining other functional groups like hydroxyl can form more stable
surface complexes than aromatic monocarboxylic acids [26]. Nev-
ertheless, the π -conjugation of aromatic monocarboxylic acid lig-
ands also strongly affects the complex’s stability, surface binding,
and charge transfer [27,28]. Therefore, one can embrace the con-
cept of molecular design to select redox-active ligand based on a
previously disclosed strategy [29].
Hereby, with benzoic acid (BA) as the initial molecule, hori-
zontally extending one or two benzene rings furnish 2-naphthoic
acid (2-NA) and 2-anthracene acid (2-AA) which could be anchored
onto TiO2 for the photocatalytic selective oxidation of sulfides. It
is worth noting that the selective oxidation of organic sulfides
has recently attracted much interest [30,31] because the resultant
sulfoxides are vital intermediates for agrochemicals, pharmaceuti-
cals, and valuable fine chemicals [32–36]. Meanwhile, TEA, an elec-
tron transfer mediator [37], maintains the integrity of these sur-
face ligands on TiO2 . Additionally, TEA also stands out for its low
boiling point in consideration of the subsequent separation and

https://doi.org/10.1016/j.cclet.2021.10.068
1001-8417/© 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
H. Li, X. Li, J. Zhou et al.
Fig. 1. (a) Horizontally extending the benzene ring of BA obtains 2-NA and 2-AA. (b) UV–vis DRS of TiO2 , BA-TiO2 , 2-NA-TiO2 , 2-AA-TiO2 . (c) Violet light-induced selective
aerobic oxidation of phenyl methyl sulfide over BA-TiO2 , 2-NA-TiO2 , 2-AA-TiO2 . Reaction conditions: CH3 OH (1 mL), ligand (1.2 × 10−3 mmol), TiO2 (40 mg), TEA (0.03 mmol),
phenyl methyl sulfide (0.35 mmol), aerial O2 , violet LEDs (3 W × 4). (d) FTIR spectra of TiO2 , 2-AA, and 2-AA-TiO2 .
purification of sulfoxides [38]. Hence, cooperative photocatalysis of
2-AA-TiO2 with TEA in solution is established via collisional elec-
tron transfer.
In general, the aromatic monocarboxylic acid-modified TiO2
complex is implemented by the acidolysis and exchange of the sur-
face hydroxyl groups of TiO2 with carboxylate anions, forming the
RCOO-Ti bond [26]. However, the π -conjugated system in aromatic
monocarboxylic acids can greatly affect the electrostatic attraction
of carboxylate anions to the titanol group, thus affecting the stabil-
ity and photocatalytic activity of the ligand-modified TiO2 . With BA
as the initial molecule, horizontally extending the π -conjugation
affords two monocarboxylic acids ligands, namely 2-NA and 2-AA
(Fig. 1a). In this work, Aeroxide P25 TiO2 was adopted as the start-
ing metal oxide to anchor BA, 2-NA, and 2-AA.
Based on the ultraviolet (UV)–visible absorption spectra (Fig.
S1a in Supporting information), it can be found that compared
with BA, there is no absorption response to visible light completely
in 2-NA, while 2-AA can harvest a band of visible light at approxi-
mately 400–420 nm. When they were assigned as redox-active lig-
ands for the surface of TiO2 , UV–visible diffuse reflectance spec-
tra (UV–vis DRS) (Fig. 1b) show that the difference between BA-
TiO2 , 2-NA-TiO2 , and pristine TiO2 is relatively small. Conversely,
the difference between 2-AA-TiO2 and pristine TiO2 is rather ob-
vious. Compared with TiO2, which can only absorb UV light, the
response range of 2-AA-TiO2 has an obvious redshift. In addition,
combining with Fig. S1b (Supporting information), Fig. 1b reveals
that the light-emitting spectrum of the violet LED overlaps with
the absorbance of 2-AA-TiO2 . Despite the loading of these ligands,
there was no change in the powder X-ray diffraction (PXRD) peaks
of rutile and anatase TiO2 (Fig. S1c in Supporting information).
Subsequently, these complexes were applied to the violet light-
induced selective oxidation of phenyl methyl sulfide (Fig. 1c). It is
intriguing to find a correlation between the conversions of phenyl
methyl sulfide and the structure of these monocarboxylic acid lig-
ands. With only one benzene ring, the photocatalytic activity of
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Chinese Chemical Letters 33 (2022) 3733–3738
BA-TiO2 was almost zero under the standard conditions. With the
augment of π -conjugation, the violet light-induced conversion of
phenyl methyl sulfide increased from 26% over 2-NA-TiO2 to 86%
over 2-AA-TiO2 for 1 h, which was attributed to the more stabilized
binding of carboxyl from 2-AA with the surface hydroxyl group of
TiO2 . Compared with anatase TiO2 (ST-01) or rutile TiO2 with much
higher specific surface areas, Aeroxide P25 TiO2 with 2-AA was the
best complex photocatalyst (Table S1 in Supporting information).
Next, the chemical states of Ti, O, and C in 2-AA-TiO2 were
measured by X-ray photoelectron spectroscopy (XPS) (Fig. S2 in
Supporting information). The Ti 2p1/2 (464.4 eV) and Ti 2p3/2
(458.5 eV) peaks conform to the results of Ti 2p (Fig. S2a), which
are consistent with a previous investigation [37]. Meanwhile, in Fig.
S2b, the XPS data of O 1s can be split into O−Ti at about 529.6 eV,
O=C at about 530.9 eV, O−C at about 531.8 eV, which might be
due to the presence of excessive 2-AA on the surface of the 2-AA-
TiO2 . According to the C 1s XPS (Fig. S2c), the carboxylate group
from 2-AA successfully combined with the titanol group of TiO2 to
generate the 2-AA-TiO2 complex.
On the other hand, the formation of 2-AA-TiO2 complex was ex-
plored by Fourier-transform infrared (FTIR) spectroscopy. In Fig. 1d,
the two broad peaks at 1423 cm−1 and 1403 cm−1 were attributed
to the stretching vibrations of –COOTi– group. The peak (1423
cm−1 ) in the FTIR spectrum of 2-AA corresponded to the sym-
metric stretching of the hydroxy group in a carboxyl group. There-
fore, it is reasonable to accept that 2-AA is successfully adsorbed
on the surface of TiO2 . Nevertheless, a more profound analysis is
required to further determine whether the binding mode of 2-AA-
TiO2 is through bidentate or monodentate via the carboxylate lig-
and. The FTIR spectra of pristine TiO2 and 2-AA were also pre-
sented in Fig. 1d. The primary signal peak of the carboxylic group
in 2-AA are analyzed as following: 1683 cm−1 is the stretching vi-
bration peak of C=O; the signal peaks at 1582 cm−1 , 1481 cm−1 ,
and 1461 cm−1 are assigned to C=C skeleton stretching mode;
the signal peak at 1423 cm−1 is the vibration peak of O−H in
H. Li, X. Li, J. Zhou et al.
Fig. 2. (a) Quenching experiments to identify the ROS for the violet light-induced selective aerobic oxidation of phenyl methyl sulfide. Standard reaction conditions: CH3 OH
(1 mL), 2-AA (1.2 × 10−3 mmol), TiO2 (40 mg), TEA (0.03 mmol), phenyl methyl sulfide (0.35 mmol), aerial O2 , violet LEDs (3 W × 4), 40 min. The EPR signals recoded
during the violet light-induced selective aerobic oxidation of phenyl methyl sulfide over the 2-AA-TiO2 photocatalyst, (b) eCB − of 2-AA-TiO2 and (c) O2 •– captured by DMPO.
carboxylate group; the strong peak at 1290 cm−1 is the stretch-
ing vibration peak of C−O [39,40]. If the 2-AA-TiO2 possesses the
monodentate mode, the FTIR spectrum of 2-AA-TiO2 should show
the vibration peak of C=O. However, the actuality that the peak
of C=O was vacant in the curve, revealed that 2-AA-TiO2 was
more tend to the bidentate binding mode. Meanwhile, the peak of
−C−O−Ti− presented in the FTIR spectrum of 2-AA-TiO2 and the
slightly shifted peak position further manifested that the two oxy-
gen atoms in the −COO− connected to the adjacent surface Ti sites
respectively and formed the bridging bidentate mode. Furthermore,
the FTIR spectra of BA-TiO2 and 2-NA-TiO2 are also shown in Fig.
S3a (Supporting information).
After confirming 2-AA-TiO2 complex, various control experi-
ments were conducted for the selective aerobic oxidation of sulfide
into sulfoxide. It can be found that photocatalyst synthesized in
situ is more effective than the pre-prepared 2-AA-TiO2 for the se-
lective aerobic oxidation of phenyl methyl sulfide to sulfoxide (Ta-
ble S2 in Supporting information). Meanwhile, kinetic studies have
shown that there is no induction time when aromatic acids mod-
ified TiO2 was in situ formed (Fig. S3b in Supporting information).
Hereafter, the exploration of the effect of different wavelengths of
LEDs is stated in Fig. S4a (Supporting information), proposing that
the corresponding conversion is commensurate to the UV–vis DRS
of 2-AA-TiO2 . In Fig. S4b (Supporting information), it was found
that very few sulfide were transformed into the corresponding sul-
foxide with 2-AA. When 2-AA was loaded onto the surface of TiO2
to form a complex photocatalyst, the conversion of phenyl methyl
sulfide was significantly improved (Fig. S4b). Synchronously, the
recycling tests were implemented to testify the durability of the
2-AA-TiO2 photocatalyst (Fig. S4c in Supporting information). The
recovered 2-AA-TiO2 was also reused twice with the temperate re-
furbishing of 2-AA, implying its superior endurance.
Importantly, all the components of the photocatalytic system
were indispensable based on the thorough control experiments.
Further, the effect of the amounts of aromatic acids was explored
(Fig. S5a in Supporting information). The conversion of phenyl
methyl sulfide sharply increased once 2-AA was added. However,
with the further increase of the dosage of 2-AA, the conversion of
phenyl methyl sulfide increased slightly. With the amount of TiO2
enhanced, the yield of phenyl methyl sulfoxide advanced gradually
and the selectivity of the product declined slightly (Fig. S5b in Sup-
porting information). TEA, the electron transfer mediator, exhib-
ited a considerable effect on the violet light-induced selective aer-
obic oxidation of sulfide over the 2-AA-TiO2 photocatalyst (Fig. S5c
in Supporting information). Furthermore, when TEA was replaced
by trimethylamine, the conversion of phenyl methyl sulfoxide de-
creased slightly (Table S3 in Supporting information). CH3 OH, as
a redox-active solvent, plays an important role in the formation
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Chinese Chemical Letters 33 (2022) 3733–3738
of phenyl methyl sulfoxide (Table S4 in Supporting information).
With the increasing power of violet LEDs, the conversion of phenyl
methyl sulfide presented an increasing trend (Fig. S5d in Support-
ing information).
Next, different scavengers were introduced into the system to
determine the reactive oxygen species (ROS) (Fig. 2a). First, a sin-
glet oxygen (1 O2 ) scavenger, 1,4-diazabicyclo[2.2.2]octane (DABCO)
was added to the reaction system. The slightly reduced conversion
indicated that 1 O2 did not produce a decisive impact on the re-
action. In contrast, when p-benzoquinone (p-BQ) was introduced
to capture O2 •– , the selective oxidation of sulfide was almost com-
pletely restrained, suggesting that O2 •– was the pivotal ROS. Nev-
ertheless, no reaction occurred in an atmosphere of N2 , suggesting
O2 is the terminal oxidant. Besides, AgNO3 completely restrained
the reaction by capturing eCB − . Furthermore, according to Fig. S6a
(Supporting information), the flat band potential that is closely re-
lated to the conduction band (CB) potential could be linearly fitted
to be −0.85 V vs. Ag/AgCl from the intercept of the x-axis, which
is negative than the potential of O2 /O2 •– (−0.48 V vs. Ag/AgCl). Ac-
cording to the value of the bandgap and the CB potential, the va-
lence band (VB) potential was calculated as +1.9 V vs. Ag/AgCl (Fig.
S6b in Supporting information).
To better comprehend the reaction process, electron paramag-
netic resonance (EPR) experiments were then carried out. The eCB −
signal of 2-AA-TiO2 gradually increased with the prolongation of
exposure time in the absence of O2 (Fig. 2b). Once O2 was poured,
the eCB − signal reduced to the initial state, indicating the relevance
between O2 and eCB − . The EPR signal of O2 •– was then tested with
5,5-dimethyl-1-pyrroline N-oxide (DMPO) as the capturing agent
(Fig. 2c). The EPR signal of O2 •– dramatically increased under vio-
let light irradiation from 0 min to 2 min and continued to slightly
increase at 4 min, suggesting that O2 •– captured by DMPO was ac-
cumulated and maintained after switching off the light.
Tentatively, a mechanism of violet light-induced selective aer-
obic oxidation of sulfide over 2-AA-TiO2 photocatalyst with TEA
is proposed in Scheme 1. Firstly, the carboxyl group of 2-AA is
in combination with the surface hydroxyl group of TiO2 , consti-
tuting the 2-AA-TiO2 photocatalyst, which enables the reaction to
take place at the violet light range. Next, the charge separation is
generated over the surface complex by the stimulation of violet
light. 2-AA would straightly infuse electrons into the CB of TiO2
to form 2-AA•+ , without running into an excited state of 2-AA∗ .
Meanwhile, O2 •– is generated by the reduction of O2 at the CB of
TiO2 . Thirdly, the transition between TEA and TEA•+ is driven by
collisional electron transfer with 2-AA•+ , and the resulted TEA•+
interacts with phenyl methyl sulfide to deliver a sulfur-centered
radical cation, which is pivotal to connect the TEA redox cycle and
photocatalytic cycle. This connection can effectively prevent the 2-
H. Li, X. Li, J. Zhou et al. Chinese Chemical Letters 33 (2022) 3733–3738

Table 1
Violet light-induced selective aerobic oxidation of sulfides into sulfoxides with air by cooperative photocatalysis of 2-AA-TiO2 with TEA.a

(continued on next page)

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H. Li, X. Li, J. Zhou et al.
Table 1 (continued)
Scheme 1. A proposed mechanism of violet light-induced selective aerobic oxidation of phenyl methyl sulfide by cooperative photocatalysis of 2-AA-TiO2 with TEA.
AA-TiO2 photocatalyst from being undermined by ROS. Fourthly,
the sulfur-centered radical cation combines with O2 •– to generate
phenyl methyl persulfoxide. Ultimately, protons from CH3 OH ter-
minate phenyl methyl persulfoxide to afford phenyl methyl sulfox-
ide.
Then, the range of organic sulfides subjected to the photo-
catalytic protocol was investigated (Table 1). Phenyl methyl sul-
fide was oxidized to corresponding phenyl methyl sulfoxide in
88% selectivity and 85% conversion for 50 min (Table 1, entry 1).
With a comparable reaction time, the sulfides containing electron-
donating groups generally afforded higher conversions than that of
phenyl methyl sulfide (Table 1, entries 2–4). On the contrary, con-
versions of sulfides containing electron-withdrawing groups were
lower than that of phenyl methyl sulfide (Table 1, entries 7–12).
The sulfides with an m–methoxy group or an o–methoxy group
holding the fairly strong steric hindrance effect desired an ex-
tended reaction time (Table 1, entries 5 and 6). A similar trend
was observed in sulfides containing electron-withdrawing groups
(Table 1, entries 11 and 12). Therefore, affected by the steric effect,
the required reaction time of the regioisomer augmented in the or-
der of para < meta < ortho isomer. In addition, when the methyl
group of phenyl methyl sulfide was replaced by an ethyl group or
a phenyl group, longer reaction time was acquired (Table 1, entries
13 and 14). The selective oxidation of 2-naphthyl methyl sulfide
took a longer time to reach a similar conversion (Table 1, entry
15). Moreover, the selective oxidation of aliphatic sulfides required
less reaction time to achieve the considerable conversion (Table 1,
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Chinese Chemical Letters 33 (2022) 3733–3738
entry 16) or achieved a higher conversion and selectivity with the
standard reaction time (Table 1, entry 17).
In summary, extending the π -conjugation of aromatic acids has
been adopted to construct TiO2 complex visible light photocata-
lysts. Intriguingly, with BA as the initial molecule, horizontally ex-
tending one or two benzene rings acquires 2-NA and 2-AA. Among
three aromatic acids, 2-AA has delivered the best result over
TiO2 due to the most extended π -conjugation. Importantly, TEA
maintains the integrity of anchored aromatic acids and accelerates
electron transfer. Conveniently, violet light-induced selective aero-
bic oxidation of sulfides to sulfoxides has been realized by cooper-
ative photocatalysis of 2-AA-TiO2 with 10 mol% of TEA. This work
extends the library of next-generation ligands for semiconductors
to expand visible light-induced selective organic reactions.
Declaration of competing interest
The authors declare that they have no known competing finan-
cial interests or personal relationships that could have appeared to
influence the work reported in this paper.
Acknowledgment
This work was funded by the National Natural Science Founda-
tion of China (Nos. 22072108 and 21773173).
H. Li, X. Li, J. Zhou et al. Chinese Chemical Letters 33 (2022) 3733–3738

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