A novel selective oxidative cleavage of C–C bond mediated by black nickel oxide in the presence of molecular oxygen

Article abstract of DOI:10.1016/j.catcom.2021.106305

A selective aerobic oxidative cleavage of C–C bond is developed with black nickel oxide (NiO_x) as the catalyst. For the oxidation of 1-phenyl-1, 2-ethanediol, a 97.5% conversion in 96.7% selectivity of benzaldehyde is obtained under 0.3 MPa of O₂ at 140 °C for 3 h. The relationship between the catalytic performance of NiO_x and structure is discussed. It is concluded that the existence of Ni³⁺ should be crucial to the activity of catalyst. Moreover, the recycling experiments showed that the catalyst can retain a high activity even after being reused for five times.

Full text of DOI:10.1016/j.catcom.2021.106305

Catalysis Communications 154 (2021) 106305
Contents lists available at ScienceDirect
Catalysis Communications
journal homepage: www.elsevier.com/locate/catcom
Short communication
A novel selective oxidative cleavage of C
oxide in the presence of molecular oxygen
–
C bond mediated by black nickel
*
*
Lingwu Meng, Wei Li , Pengfei Guo, Shun Wang, Xinli Tong
Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin
3
00384, PR China
A R T I C L E I N F O
A B S T R A C T
Keywords:
x
A selective aerobic oxidative cleavage of C C bond is developed with black nickel oxide (NiO ) as the catalyst.
–
For the oxidation of 1-phenyl-1, 2-ethanediol, a 97.5% conversion in 96.7% selectivity of benzaldehyde is ob-
Heterogeneous catalysis
1
, 2-diols
C bond cleavage
◦
tained under 0.3 MPa of O
2
at 140 C for 3 h. The relationship between the catalytic performance of NiO
x
and
C
–
3+
structure is discussed. It is concluded that the existence of Ni should be crucial to the activity of catalyst.
Moreover, the recycling experiments showed that the catalyst can retain a high activity even after being reused
for five times.
Nickel oxide
Molecular oxygen
1
. Introduction
optimized conditions [8]. Subsequently, Neumann’s group [9] found
that the carbon‑carbon bond cleavage of D-glucose was performed suc-
The selective oxidative carbon‑carbon (C
–
C) bond cleavage of
cessfully with H
cient carbon‑carbon bond cleavage of 1, 2-diols was achieved using
vanadium complex or Mn (CO)10 as the homogeneous catalyst [10,11].
Also, several nickel complexes were found to be very efficient to the
aliphatic cleavage of C
C bond at ambient conditions [12–16].
Furthermore, Schwarz et al. employed a simple CeCl as catalyst to
5 2
[PV Mo10O40] as the catalyst. Then, the aerobic effi-
organic compounds is a very significant technology for converting large
molecules to the smaller ones [1,2]. Further, this process is very useful
for biomass transformation, considering that the existence of numerous
C - C inter-unit linkage in the structure of cellulose, hemicellulose and
lignin [3]. Generally, the oxidative cleavage reaction is considered to be
a synthetic method to generate carbonyl groups in organic chemistry. In
traditional methods, the inorganic oxidants such as potassium perman-
ganate, lead tetraacetate, chromium trioxide, manganese dioxide,
DMSO, sodium and potassium periodate were employed for oxidative
cleavage processes under heating conditions [4–7]. For example,
Sudalai’s group found that the carbon‑carbon bond cleavage of 1, 2-diols
2
–
3
achieve the cleavage of vicinal diol under blue light in air [17]. Very
recently, the green and aerobic oxidative cleavage process of vicinal diol
was successfully performed using carbon nitrides as catalyst in micellar
medium under the visible light [18].
Furthermore, to resolve the low stability and poor recyclability of
homogeneous metallic catalyst, the heterogeneous solid catalysts were
paid great attentions owing to their excellent stability and good recy-
clability. In particular, transition metal oxides represent the main het-
erogeneous catalysts used in industry [19]. In 2017, Anasta’s group
[20,21] discovered that a mixed oxide of Na and Mn (Na-Mn-LMO) or
Mn oxide from biomass of Mn-hyperaccumulating plant could efficiently
promote the oxidative carbon‑carbon bond cleavage of 1, 2-diols in 1-
butanol. As a result, different aldehydes or ketones can be prepared
4
was achieved using an excess of NaIO reagents in dichloromethane [5].
However, the use of these excess oxidants is disadvantageous and not
popular in the present chemistry, owing to their high toxicity, difficult
storage and high cost; meanwhile, the produced hazardous wastes were
harmful to the environment. Therefore, it is necessary to develop a
highly efficient, environment-friendly and economic approach, in which
molecular oxygen as oxidant is clean and green for the oxidative
processes.
2 3
using K CO as the additive and using molecular oxygen as an oxidant
In recent years, the oxidative cleavage of 1, 2-diols with molecular
under the suitable conditions. Luo et al. [22] studied the oxidative
cleavage of 1, 2-diols with an atomically dispersed Co-based heteroge-
neous catalyst supported on N-doped carbon materials, in which several
reactants could be efficiently transformed to corresponding aldehydes in
oxygen has been investigated. Therein, Wang et al. employed Pd (OAc)
and Na CO as the catalyst to promote the carbon‑carbon bond cleavage
of 1, 2-diols where a 95% yield of benzaldehyde was acquired under the
2
2
3
*
Corresponding authors.
E-mail addresses: weili1024@163.com (W. Li), tongxinli@tju.edu.cn (X. Tong).
https://doi.org/10.1016/j.catcom.2021.106305
Received 6 November 2020; Received in revised form 9 February 2021; Accepted 12 March 2021
Available online 16 March 2021
1
566-7367/© 2021 The Author(s).
Published by Elsevier B.V. This is an open access article under the CC BY-NC-ND license
(
http://creativecommons.org/licenses/by-nc-nd/4.0/).

L. Meng et al.
Catalysis Communications 154 (2021) 106305
the presence of K
2
CO
3
as additive. Moreover, Solmi et al. [23] used the
Table 1
The oxidative C–C bond cleavage of 1 with different catalysts [
a]
.
Au/MgO catalyst for the oxidative cleavage of trans-1, 2-cyclohexane-
diol with air, in which a close to 70% selectivity of adipic acid was
attained under the optimal conditions.
[b]
[b]
Entry
Catalyst
Conversion (%)
Product Distribution (%)
2
3 + 4
The application of nickel element recieved substantial attentions
because of its rich content and low toxicity [24]. Particularly, nickel
oxide (NiO) is a solid material with ferromagnetic properties and its Neel
temperature is about 523 K. Correspondingly, the NiO has some unique
electrical, magnetic, and optical properties that make it greatly popular
in traditional field [25]. Thus, the NiO is often employed as the sensor
1
NiO-H
NiO-C
NiO-U
14.0
34.7
49.4
61.1
11.7
27.7
4.6
98.7
99.6
99.8
98.5
100
1.3
0.4
0.2
1.5
–
2
3
4
NiO
x
5
NiO-250
NiO-400
NiO-500
NiO-300
6
99.8
98.1
100
0.2
1.9
–
7
[
26], the photoelectrochemical device [27–29], the battery [30] and
[
c]
8
1.7
electro chromic film [31,32]. Also, the supported NiO nanosheet is
considered as the supercapacitor [33]. However, use of nickel oxide as
the efficient heterogeneous catalyst is relatively inadequate, except that
the K/Ca/Ni oxide system was investigated on the oxidative coupling
process of methane [34].
[d]
9
NiO-300-A
NiC O
29.3
2.1
97.5
100
2.5
–
10
11
2 4
no
NiO
0.3
100
–
[
e]
1
2
x
97.5
96.7
3.3
[a] Reaction conditions: 0.2 g of 1, 0.05 g of nickel oxide catalyst, in 20 mL
◦
In this communication, the simple and low-cost black nickel oxide
methanol, under 0.3 MPa of oxygen, at 100 C, for 4 h. [b] The data were
(
NiO
x
) was employed as the catalysts to perform the oxidative cleavage
attained by GC using the internal standard technique. [c] The NiO-300 catalyst is
◦
prepared via the calcination of NiC
2
O
4
under N
2
300 C. [d] NiO-300-A is ob-
of 1, 2-diols in aliphatic alcohols. Based on the experimental results, it
was found that, for the oxidation of 1-phenyl-1, 2-ethanediol, a 97.5%
tained by continuous treatment of the catalyst in entry 8 under air atmosphere at
◦
◦
3
00 C. [e] The reaction is performed at 140 C for 3 h.
conversion in 96.7% selectivity of benzaldehyde was obtained under 0.3
◦
MPa of O
2
at 140 C for 3 h. Nickel oxalate-derived catalyst is the most
active for the oxidative C C bond cleavage reaction. The relationship
–
2
.3. The preparation of the NiO-U catalyst
x
between the catalytic performance of NiO and material structure is
discussed. The existence of Ni3 should be crucial to the activity of
+
About 4.9772 g of nickel acetate was dissolved in a solution of 30 mL
of ultrapure water and 30 mL of ethylene glycol. Under stirring, the urea
6.0 g) and polyvinylpyrrolidone (PVP, 0.13 g) were added to above
catalyst. Furthermore, recycling experiments showed that the catalyst
still retains a high activity even after being reused for five times.
(
solution. Then, the mixture was transferred to Teflon-lined autoclave for
◦
hydrothermal crystallization at 180 C for 5 h. After being cooled to
2
. Experimental section
room temperature, the solid product is obtained through the centrifu-
gation. Thereafter, the solid was washed by the distilled water and
anhydrous ethanol several times, and then dried under vacuum. Finally,
2
.1. Reagents and equipment
◦
the NiO-U was prepared through calcination at 300 C for 2 h.
All reagents and chemicals used were of analytical grade unless
otherwise specified. Nickel nitrate; oxalic acid, urea, 1-phenyl-1, 2-
2
.4. The preparation of NiO catalyst
x
ethanediol, hydro benzoin, 2-methoxy-1, 2-diphenylethanone, 2-hy-
.
3
droxy-2-phenylacetic acid, Na
2
CO
3
,
NH
H
2
O, NaOH, methanol,
About 5.816 g of Ni (NO ) was dissolved in 20 mL of water; then, the
3 2
ethanol, n-propanol, i-propanol, n-butanol and n-pentanol are of
analytical grade and used without further treatment. The standard
samples of benzaldehyde and methyl benzoate are purchased from Alfa
Aesar.
2
5% ammonia water was dropped until pH = 8.0 (Solution A); In
addition, about 3.78 g of oxalic acid was dissolved in 20 mL of distilled
water (Solution B). Next, the solution B was slowly added into solution
An under stirring to pH 7.0. The obtained mixed solution was stirred at
The measurement of X-ray diffraction (XRD) was performed by a
◦
◦
60 C for 4 h. After cooling to the room temperature, the solid products
diffractometer with Cu Ka radiation and was collected from 5 to 80 [2θ]
were attained through the centrifugation, then, the product was dried
with a resolution of 0.02 degree. The surface morphology and particle
size of solid catalysts were detected by scanning electron microscope
under a vacuum condition. Finally, the NiO
x
material was prepared after
◦
being calcined at 300 C for 2 h.
(
(
SEM) (JSM-6301F, JEOL) and transmission electron microscope (TEM)
JEM-2100, JEOL). The pore structures of heterogeneous catalysts were
2
.5. General procedure for selective oxidative cleavage of C
–
C bond
detected by the Micromeritics ASAP2020M system. Fourier transform
infrared (FT-IR) spectra were recorded on a Nicolet Nexus spectrometer
ꢀ 1
The oxidative carbon‑carbon bond cleavage reaction of substrate was
in the 400–4000 cm range. The oxidation states of nickel in the cat-
alysts were tested by H TPR technique. The analysis of the product was
performed in a 120 mL stainless-steel autoclave with the magnetic
stirring. The general procedure for oxidative transformation of 1-
phenyl-1, 2-ethanediol is described as follows: 0.200 g of reactant,
2
carried out on the Agilent 6890/5973 Gas Chromatograph-Mass Spec-
trometer (GC–MS) instrument.
0
x
.050 g of NiO catalyst, and 20 mL of methanol were added to the
autoclave, respectively. The atmosphere in the reactor was exchanged
by pure oxygen for thrice. Then 0.3 MPa of dioxygen was charged into
the reactor after being sealed. Next, the temperature was raised to
2
.2. The preparation of the NiO-H and NiO-C solid catalysts
Approximately 5.816 g of Ni(NO was dissolved in 20 mL of
◦
3
)
2
140 C, and was kept for 3 h. After reaction, the mixture was slowly
deionized water. Under stirring, the 0.1 M NaOH solution was slowly
cooled and the excessive gas was discharged. Finally, the solid NiO
x
added until the pH value retains in the range of 8–9; then, the mixture
catalyst was separated by the filtration, and the products were analyzed
by the Gas Chromatography (GC) with a hydrogen ion flame detector
using the internal standard technique.
◦
was further stirred at 60 C for 4 h. After being cooled to room tem-
perature, the solid product was obtained by the centrifugation. There-
after, the solid was washed by the distilled water and anhydrous ethanol
several times, and then dried under vacuum. Finally, the NiO-H was
3. Results and discussion
◦
prepared through being calcined at 300 C for 2 h.
The preparation of NiO-C catalyst is similar to that of NiO-H catalyst
Initially, aerobic oxidative cleavage of 1-phenyl-1, 2-ethanediol (1)
but uses Na
2
CO
3
solution instead of NaOH solution.
was used as the model reaction to investigate the activity of different
2

L. Meng et al.
Catalysis Communications 154 (2021) 106305
Fig. 1. The
H
2
-TPR detection of nickel oxides prepared using
Fig. 2. Influence of solvent in oxidative C–
1
C bond cleavage reaction (0.20 g of
different methods.
◦
, 0.05 g NiO
x
2
, 20 mL solvent, under 0.3 Mpa of O , at 140 C, for 3 h).
catalyst (Eq. 1), in which the main product is benzaldehyde (2) and the
obtained by-products include methyl benzoate (3) or (dimethox-
ymethyl)benzene (4) during reaction. The experimental results are
summarized in Table 1.
2 4
attained with NiC O as the catalyst (entry 10). The blank experiment
shows that less than 1% conversion (about 0.3%) of 1 is obtained in the
absence of any catalyst (entry 11). Notably, a 97.5% conversion of 1
◦
with 96.7% selectivity of 2 is attained at 140 C for 3 h (entry 12), which
(
1)
In the presence of NiO-H catalyst (prepared using sodium hydroxide
as precipitant), a 14.0% conversion of 1 in 98.7% selectivity of 2 was
obtained in methanol solvent (entry 1). When NiO-C (prepared using
sodium carbonate as precipitant) or NiO-U (prepared using urea as the
precipitant) was used as catalyst, a 34.7% or 49.4% conversion of 1 is
attained (entries 2 and 3). Furthermore, the NiO
x
(originated from
◦
calcination of NiC
2
O
4
at 300 C) exhibits very high catalytic activity, in
which the conversion of 1 can arrive at 61.1% under similar conditions
entry 4). These indicate that the synthesis processes of nickel oxide and
(
the corresponding precursors are closely related to the catalytic per-
formance and that nickel oxalate-derived catalyst is the most active for
oxidative C C bond cleavage reaction.
–
In addition, the effect of calcination temperature was further inves-
tigated for this process. As a result, it is found that 11.7%, 27.7 or 4.6%
conversion of 1 was obtained when NiO-250 (prepared from calcination
◦
2
of NiC O
4
at 250 C), NiO-400 or NiO-500 was employed as the catalyst
(
2 4
entries 5, 6 and 7), respectively. These results indicated that the NiC O
◦
being calcined at 300 C is beneficial to promote reaction. Conversely,
when the NiO is prepared via the calcination of NiC under nitrogen
atmosphere, the activity remains substantially low and the conversion of
is about 1.7% (entry 8). In the following, after the above NiO is further
2 4
O
1
x
Fig. 3. Recycling of NiO on the oxidative C C bond cleavage of 1 Reaction
–
treated under air, the conversion of 1 can reach 29.3%, which demon-
conditions: 0.20 g of 1, 0.05 g catalyst, 0.005 g K
2
CO
3
, in 20 mL methanol,
strates that the generation of Ni3 is responsible for the oxidative
+
◦
under 0.3 Mpa of O
2
, at 140 C, for 3 h).
cleavage process (entry 9). As comparison, only 2.1% conversion of 1 is
3

L. Meng et al.
Catalysis Communications 154 (2021) 106305
◦
Table 2
more than thrice; next, the obtained sample is further dried at 80 C for
The oxidative C
–
C bond cleavage of different 1, 2-diols with the NiO
x
catalyst
12 h in a vacuum oven and then used as catalyst in the following re-
[
a]
.
x
actions. As shown in Fig. 3, the solid NiO catalyst still exhibited a high
Entry
Reactants
Conversion
Product distribution
[b]
activity and good selectivity even after being employed for four times.
[
b]
(
%)
(%)
The conversion of 1 is still over 95% and the selectivity of 2 remains
nearly unchanged. The experimental results indicate that the NiO
x
Aldehyde
98.8
Others
1.2
catalyst can be recycled and reused during the oxidative C
cleavage processes.
–
C bond
1
2
3
4
5
6
(1R,2S)-1,2-diphenylethane-
99.0
96.7
96.5
92.1
94.3
98.9
1
,2-diol
(1R,2R)-1,2-diphenylethane-
,2-diol
>99.0
>99.0
>99.0
96.5
–
Finally, the selective oxidation processes of different substrates were
investigated with NiO catalyst. The obtained experimental data from
1
x
(1S,2S)-1,2-diphenylethane-1,2-
diol
–
the oxidative cleavage processes are given in Table 2. As a result, it can
be seen that more than 90.0% yields of corresponding aldehydes were
obtained when different 1, 2-diols were employed, which further con-
–
firms that NiO catalyst is very high efficient for the oxidative C C bond
x
cleavage of vinical diols in the presence of oxygen. However, when the
1,2-bis(4-fluorophenyl)ethane-
–
1
,2-diol
1,2-bis(4-bromophenyl)ethane-
,2-diol
1,2-bis(2-chlorophenyl)ethane-
,2-diol
3.5
–
1
>99.0
oxidation of 2-methoxy-1, 2-diphenylethanone was carried out with
1
[
c]
c]
x
NiO catalyst in methanol, a 99.0% conversion with a 98.5% selectivity
7
8
1, 2-di-p-tolylethane-1,2-diol
1-(pyridin-2-yl)-2-(pyridin-3-yl)
ethane-1,2-diol
91.4
96.9
>99.0
–
1.7
98.3
of methyl benzoate was attained. Meanwhile, 2-hydroxy-2-phenylacetic
acid could be selectively converted to produce (dimethyoxymethyl)
[
[d]
9
1
2-methoxy-1, 2-
>99.0
>99.0
98.5
1.5
1.8
benzene in methanol. These results showed that NiO
x
catalyst can pro-
diphenylethanone
–
mote oxidative cleavage of C C bond of different reactants in the
presence of molecular oxygen.
[
e]
0
2-hydroxy-2-phenylacetic acid
98.2
[
a] Reaction conditions: 0.10 g of reactant, 0.05 g of the NiO
x
catalyst, in 20 mL
◦
of methanol, under 0.3 MPa of oxygen, at 100 C, for 3 h. [b] The data were
attained by GC using the internal standard technique. [c] The reaction is per-
4
. Conclusions
◦
formed at 140 C. [d] The main product is methyl benzoate. [e] The obtained
In summary, a novel and efficient oxidative cleavage process of 1, 2-
diols and their derivatives with NiO catalyst was achieved. In the
main product is (dimethylhydroxy)benzene in the methanol solvent.
x
oxidation of compound 1 and hydrobenzoin, a 94.3% and 97.8% yield of
indicates that the conversion of 1 is obviously improved and that the
selectivity of 2 still maintains unchanged almost when the temperature
is elevated.
benzaldehyde was respectively obtained. Thus, nickel oxalate derived
catalyst is the most active for oxidative C C bond cleavage reaction,
–
compared to other catalyst precursors. Moreover, it was found that the
The reduction behavior and oxidative states of nickel oxides were
calclination temperature plays a key role on the preparation of NiO
x
characterized by temperature-programmed reduction (H
surement, and the results are given in Fig. 1. Generally, the reduction
peaks should be related to the transformation of Ni to NiO and the
2
-TPR) mea-
◦
with 300 C being optimal. Furthermore, recycling experiments showed
that the catalyst still maintains a high activity even after being reused
five times. This provides a novel and efficient approach for the catalytic
valorization of biomass and biomass-derived platform compounds.
2 3
O
following the reduction of NiO to Ni during reaction [35]. The corre-
sponding temperature may respond the characters of nickel oxides. If the
temperature of peaks is lower, the corresponding nickel oxide nano-
material is more active on the catalytic reaction. On the basis of the
obtained experimental results, it can be observed that the strongest
Declaration of Competing Interest
◦ ◦
For the paper titled as “A novel selective oxidative cleavage of C-C
bond mediated by black nickel oxide in the presence of molecular oxy-
gen” submitted to the Catalysis Communications journal, the authors
declare that they have no known competing financial interests or per-
sonal relationships that could have appeared to influence the work re-
ported in this paper.
peaks of commercial NiO and Ni
respectively. In addition, both of them belong to the wide peaks.
Furthermore, the peaks of the as-prepared nickel oxides including NiO
2 3
O are located at 430 C and 340 C,
x
,
NiO-H, NiO-C, NiO-400 and NiO-500 are located at between 250 and
◦
4
00 C, where most of them are the relatively sharp peaks except that of
the NiO-C material. In particular, the reduction temperature of NiO
x
◦
catalyst is between 210 and 305 C and the temperature of the corre-
◦
Acknowledgements
sponding peak is at 265 C. These demonstrated that NiO
x
still remains
very active and easily activated under the suitable conditions.
Furthermore, the selective oxidative C C bond cleavage reaction of
with NiO catalyst was further investigated in various aliphatic alco-
–
This work is financially supported by the National Natural Science
Foundation of China (No. 21878235 and 21336008).
1
x
hols. As shown in Fig. 2, a 59.8% conversion of 1 and 99.6% selectivity
of 2 was obtained in ethanol, in which the conversion of the reaction is a
little lower than that in methanol. Otherwise, when the selective
oxidative cleavage process was performed in n-propanol or i-propanol
solvent, a 67.0% or 52.7% conversion of 1 was attained, where the
selectivity of 2 still remained more than 99% during the reaction. In
addition, a 64.1% or 61.3% conversion of 1 was achieved when the n-
butanol or n-pentanol was employed as the solvent, which is similar to
that using ethanol as solvent in this reaction. These results clearly
showed that the methanol should be a preferable solvent for the selec-
Appendix A. Supplementary data
Supplementary data to this article can be found online at https://doi.
org/10.1016/j.catcom.2021.106305.
References
[
[
1] P. Sivaguru, Z.K. Wang, G. Zanoni, X. Bi, Chem. Soc. Rev. 48 (2019) 2615–2656.
2] E. Amadio, R.D. Lorenzo, C. Zonta, G. Licini, Coord. Chem. Rev. 301-302 (2015)
1
47–162.
tive oxidative C
To study the stability of NiO
ments were performed for the oxidative C
–
C bond cleavage of 1, 2-diols.
catalyst system, the recycling experi-
C bond cleavage reaction of
in the presence of molecular oxygen. After the first catalytic run, the
[3] J. Ma, S. Shi, X. Jia, F. Xia, H. Ma, J. Gao, J. Xu, J. Energy Chem. 36 (2019) 74–86.
[
[
[
4] H.S. Outram, S.A. Raw, R.J.K. Taylor, Tetrahedron Lett. 43 (2002) 6185–6187.
5] A. Sudalai, A. Khenkin, R. Neumann, Org. Biomol. Chem. 13 (2015) 4374–4397.
6] S.C. Dakdouki, D. Villemin, N. Bar, Eur. J. Org. Chem. (2011) 4448–4454.
x
–
1
[7] N. García, R. Rubio-Presa, P. García-García, M.A. Fern a´ ndez-Rodríguez, M.
R. Pedrosa, F.J. Arn ´a iz, R. Sanz, Green Chem. 18 (2016) 2335–2340.
x
black solid NiO catalyst is filtered and washed by anhydrous ethanol for
[
8] A. Wang, H. Jiang, J. Organomet. Chem. 75 (2010) 2321–2326.
4

L. Meng et al.
9] B.B. Sarma, R. Neumann, Nat. Commun. 5 (2014) 4621.
Catalysis Communications 154 (2021) 106305
[
[22] H. Luo, L. Wang, S. Shang, J. Niu, S. Gao, Commun. Chem. 2 (2019) 17.
[23] S. Solmi, E. Rozhko, A. Malmusi, Appl. Catal. A Gen. 557 (2018) 89–98.
[24] L. Zhang, D. Shi, T. Liu, M. Jaroniec, J. Yu, Mater. Today 25 (2019) 35–65.
[25] Y. Ichiyanagi, N. Wakabayashi, J. Yamazaki, Physic. B: Conden. Matter. 329 (2003)
862–863.
[
10] E. Amadio, J. Gonz a´ lez-Fabra, D. Carraro, W. Denis, B. Gjoka, C. Zonta, K. Bartik,
F. Cavani, S. Solmi, C. Bo, G. Licini, Adv. Synth. Catal. 360 (2018) 3286–3296.
11] S. Meng, L. Lin, X. Luo, H. Lv, J. Zhao, A.S.C. Chan, Green Chem. 21 (2019)
[
6
187–6193.
[
[
12] C.J. Allpress, A.M. Arif, L.M. Berreau, Chem. Eur. J. 17 (2011) 14962–14973.
13] L.M. Berreau, T. Borowski, K. Grubel, C.J. Allpress, J.P. Wikstrom, M.E. Germain,
E.V. Rybak-Akimova, D.L. Tierney, Inorg. Chem. 50 (2011) 1047–1057.
[26] E.L. Miller, R.E. Rocheleau, J. Electrochem. Soc. 144 (1997) 3072–3077.
[27] M. Awais, E. Gibson, J.G. Vos, D.P. Dowling, A. Hagfeldt, D. Dini,
ChemElectroChem. 1 (2014) 384–391.
[
[
14] C.J. Allpress, L.M. Berreau, Coord. Chem. Rev. 257 (2013) 3005–3009.
15] R. Ramasubramanian, K. Anandababu, M. Kumar, R. Mayilmurugan, Dalton Trans.
[28] S. Sheehan, G. Naponiello, F. Odobel, D.P. Dowling, A.D. Carlo, D. Dini, J. Solid
State Electrochem. 19 (2015) 975–986.
4
7 (2018) 4049–4053.
[29] M. Bonomo, G. Naponiello, I. Venditti, V. Zardetto, A.D. Carlo, D. Dini,
J. Electrochem. Soc. 164 (2017) 137–147.
[
16] J.G.D. Elsberg, A. Peterson, A.L. Fuller, L.M. Berreau, Dalton Trans. 49 (2020)
7
564–7575.
[30] H. Yang, Q. Dong, X. Hu, X. Ai, S. Li, J. Power Sources 79 (1999) 256–261.
[31] G. Wang, X. Lu, T. Zhai, Y. Ling, H. Wang, Y. Tong, Y. Li, Nanoscale. 4 (2012)
3123–3127.
[
[
17] J. Schwarz, B. K o¨ nig, Chem. Commun. 55 (2019), 486–388.
18] T. Niu, S. Chen, M. Hong, T. Zhang, J. Chen, X. Dong, B. Ni, Green Chem. 22 (2020)
5
042–5049.
19] P.T. Anastas, M.M. Kirchhoff, T.C. Williamson, Appl. Catal. A Gen. 221 (2010)
–13.
20] V. Escande, C.H. Lam, P. Cois, P.T. Anasta, Angew. Chem. Int. Ed. 56 (2017)
561–9565.
21] V. Escande, C.H. Lam, C. Grison, P.T. Anasta, ACS Sustain. Chem. Eng. 5 (2017)
214–3222.
[32] M.P. Browne, H. Nolan, N.C. Berner, Int. J. Electrochem. Sci. 11 (2016)
6636–6647.
[
[
[
3
[33] H. Yan, D. Zhang, J. Xu, Y. Lu, Y. Liu, K. Qiu, Y. Zhang, Y. Luo, Nanoscale Res. Lett.
9 (2014) 424.
9
[34] K.M. Dooley, S.Y. Chen, J.R.H. Ross, J. Catal. 145 (1994) 402–408.
[35] F. Yu, X. Xu, H. Peng, H. Yu, Y. Dai, W. Liu, J. Ying, Q. Sun, X. Wang, Appl. Catal.
A: General 507 (2015) 109–118.
3
5