Engineering zirconium-based UiO-66 for effective chemical conversion of d-xylose to lactic acid in aqueous condition

Article abstract of DOI:10.1039/d0cc03424j

Utilizing metal-organic frameworks (MOFs) as heterogeneous catalysts is an interesting and important application due to their well-controlled catalytic sites and well-defined porous structures. In this study we apply, for the first time, Zr-based UiO-66 for the catalytic hydrothermal conversion of d-xylose to lactic acid (LA). The reactions are catalyzed by the coordinatively unsaturated Zr4+, as Lewis acid sites, and the hydroxide ion (OH-) located at the defect sites. The catalytic performances of UiO-66 catalysts synthesized through a modulator-free approach (UiO-66) and an acetic acid modulator-assisted approach (UiO-66(AA)) are distinct due to the different concentrations of local defects. The UiO-66 catalyst possessing a higher defect concentration exhibits a superior LA yield of 1.17 mol from 1 mol of xylose. However, the UiO-66(AA) catalyst with higher crystallinity shows better selectivity for LA over furfural, a side product from the competitive pathway. The enhanced LA yield and excellent selectivity can be achieved by the removal of AA from UiO-66(AA) resulting in a novel MOF catalyst (UiO-66(AA)?) which provides more accessible catalytic sites with retained crystallinity. This work highlights that the structural engineering of MOF catalysts is crucial for the fine-tuning of their catalytic properties. This journal is

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DOI: 10.1039/D0CC03424J
ARTICLE
Engineering Zirconium-based UiO-66 for Effective Chemical
Conversion of D-Xylose to Lactic Acid in Aqueous Condition
Panyapat Ponchai,a Kanyaporn Adpakpang,a Sutarat Thongratkaew,b Kawisa Chaipojjana,b
Suttipong Wannapaiboon,c Siwarut Siwaipram,a Kajornsak Faungnawakij,b and Sareeya
Bureekaew*a,d
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
Utilizing metal-organic frameworks (MOFs) as heterogeneous catalysts is one of interesting and important applications due
to their well-controlled catalytic sites and well-defined porous stuctures. In this study we apply, for the first time, Zr-based
UiO-66 for the catalytic hydrothermal conversion of D-xylose to lactic acid (LA). The reactions are catalyzed by the
coordinatively unsaturated Zr4+, as Lewis acid sites, and the hydroxide ion (OH) located at the defect sites. The catalytic
performances of UiO-66 catalysts synthesized through modulator-free approach (UiO-66) and acetic acid modulator-assisted
approach (UiO-66(AA)) are distinct due to the different concentrations of the local defects. The UiO-66 catalyst possessing
higher defect concentration exhibits superior LA yield of 1.17 mol from 1 mol of xylose. However, UiO-66(AA) catalyst with
higher crystallinity shows better selectivity for LA over furfural, a side product from the competitive pathway. The enhanced
LA yield and excellent selectivity can be achieved by the AA removal of UiO-66(AA) resulting in the novel MOF catalyst (UiO-
66(AA)*) which provides more accessible catalytic sites with the retained crystalinity. This work highlights that the structural
engineering of MOF catalysts is crucial for the fine-tuning of their catalytic properties.
nodes. Consequently, the Brønsted acid moieties in the MOFs
catalysts are usually introduced by post-functionalization of the
organic linkers or by post-incorporation of the functionalized
Introduction
Metal-organic frameworks (MOFs) have received increasing
attention as potential heterogeneous catalysts in biomass
upgrading.1 Owing to the abundance of active sites together
with the similar features of all catalytic sites activating the
chemical reaction in the uniformly confined pores, one can
expect high catalytic efficiency and high selectivity from MOF
catalysts.2 Catalytic conversion of commodity products such as
sugars into industrial chemicals is one of value-added strategies
for the industrial commerce. Some research groups focus on
using MOFs for the dehydration of C5 and C6 sugars to form
valuable furan compounds, i.e. furfural and 5-
hydroxymethylfurfural (HMF-5), respectively. This reaction can
be effectively proceeded under Brønsted-acidic catalytic
condition.3 However, it is difficult to maintain Brønsted acid (H+)
in the framework, since the organic ligands are typically
deprotonated in order to coordinate to the transition metal
compounds to the unsaturated inorganic nodes.4 Apart from
the abovementioned pathway, sugars can be alternatively
decomposed into other smaller-size, valuable compounds such
as erythrose (C4), lactic acid (LA; C3) and glyceraldehyde (C3) via
the CC bond cleavage retro-aldol condensation.5 Notably, this
reaction pathway requires Lewis acids as catalyst. Even though
the Lewis acidity is found in MOFs consisting of coordination-
unsaturated metal sites (CUSs; also named as open metal sites),
such MOFs are scarcely used for retro-aldol condensation.
LA is one of important C3-chemicals, which are typically
used in cosmetic, pharmaceutical and (biodegradable)polymer
industries.6 Remarkably, over 90% of the commercially-
available LA is produced from biotechnological fermentation,
which encounters several drawbacks such as low reaction rate,
high energy consumption and a large amount of waste
produced during the neutralization. Therefore, such
production of LA using chemical synthesis methods has been
alternatively developed.7 In general, LA can be synthesized
from monosaccharides and disaccharides using heterogeneous
catalysts via the CC bond cleavage followed by the hydride
shift.5a-c While many studies demonstrated the conversion of
C6 sugars to LA,7b,8 the LA conversion from C5 sugar such as
xylose has been rarely investigated. Theoretically, the CC
bond cleavage of C6 sugars occurs via either C2+C4, C3+C3, or
both pathways, whereas C5 sugars mainly follows the C2+C3
pathway.9 In order to avoid the complexity upon various
competitive reactions when using C6 sugars as the reactant, C5
a. School of Energy Science and Engineering, Vidyasirimedhi Institute of Science and
Technology, 555 Moo 1 Payupnai, Wangchan, Rayong 21210, Thailand.
b. National Nanotechnology Center (NANOTEC), National Science and Technology
Development Agency (NSTDA), 111 Thai-land Science Park, Pahonyothin Rd.,
Klong Luang, Pathumthani 12120, Thailand.
c. Synchrotron Light Research Institute, 111 University Avenue, Muang, Nakhon
Ratchasima 30000, Thailand.
d. Research Network of NANOTEC-VISTEC on Nanotechnology for Energy,
Vidyasirimedhi Institute of Science and Technology, Wangchan, Rayong, 21210,
Thailand
† Footnotes relating to the title and/or authors should appear here.
Electronic Supplementary Information (ESI) available: [details of any supplementary
information available should be included here]. See DOI: 10.1039/x0xx00000x
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(a)
(b)
Without using the catalyst, the D-xylose conversion is
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52.94% providing furfural (0.37 mol) as tDhOeIm: 10a.i1n03p9r/oDd0uCcCt0.3O42n4lyJ
small amount of LA (0.03 mol) was produced, while other by-
products such as acetic acid and formic acid were obtained with
sparse amount. It clearly indicated that the dehydration of D-
xylose to furfural is the preferable pathway in the catalyst–free
hydrothermal conversion.5b The result suggests that the
production of high LA yield with high selectivity over furfural
requires the usage of effective catalysts.
Figure 1. Building units of UiO-66 with (a) ideal molecular
UiO-66 effectively promotes the retro-aldol condensation
structure and (b) one missing carboxylate linker, which provides converting D-xylose to LA with high conversion of 98.26% and
two defective Zr sites coordinated with water and hydroxide high LA yield of 1.17 mol. Additionally, furfural was found in
anion. Under the hydrothermal reaction at elevated small fraction of 0.20 mol. As the reaction was conducted in
temperature, the coordinated H2O can be detached from Zr4+ aqueous system, the conversion of D-xylose to furfural can be
generating the accessible Lewis acid Zr sites. Zr, O, C, and H are possible, suggested by the controlled experiment of the
labelled in blue, red, brown, and white, respectively.
catalytic-free condition. As mentioned previously, the CC bond
cleavage of C5 D-xylose via the retro-aldol condensation
D-xylose was rationally chosen for the LA conversion in this produces the equimolar C2 and C3 intermediates. Further, the
study. C3 intermediate is converted to LA by the hydride shift (Figure
Herein, the use of MOF as a catalyst in the retro-aldol S8). Interestingly, the extensively high yield of LA could be
condensation for D-xylose (C5 sugar) conversion to LA was attributed to the ability of UiO-66 to additionally convert the C2
investigated for the first time. Specifically, Zr-based UiO-66 can residues to LA.12 The catalytic activity is far better than the
efficiently convert D-xylose to LA without the modification on benchmark ZrO2 catalyst which shows D-xylose conversion of
organic linkers and/or inorganic nodes. UiO-66 is well-known as 77.84% and produces 0.55 mol LA, and 0.40 mol furfural. In the
a framework with high chemical and thermal stability. case of ZnO, even though the conversion was 99.55 %, the
It consists of [Zr6O4(OH)4]12+ inorganic building units and the amount of the obtained LA was approximately 3 times less than
benzene-1,4-dicarboxylate (BDC) linkers.10 In principle, Zr4+ ions that from the UiO-66. However, the high selectivity of LA over
within UiO-66 are fully coordinated with 8 oxygen atoms  4 furfural is still observed. The mostly-complete D-xylose
from carboxylate, 2 from µ3OH and 2 from µ3O. Theoretically, conversion but the less amount of both LA and furfural suggests
the coordinatively saturated framework of the perfect UiO-66 the formation of other products when using the ZnO catalyst.
crystals therefore does not provide any catalytically active sites.
Suggested by the computational simulation that the missing
However, it is known that UiO-66 usually exhibits the excellent linkers create the catalytically active Zr sites (Figure S7), the
catalytic performances in various acid-catalyzed reactions.11 modulator approach has been employed to manipulate these
Those catalytic performances are attributed to the Lewis acidic defects in the catalyst framework. It is known that the addition
character of the defective Zr nodes generated by the missing of of modulators could alter the properties of MOFs e.g.
organic linkers. These local defective Zr ions are then occupied morphology, crystallinity and defect attributes.13 By using acetic
by the coordination of water molecule and hydroxide ion (OH), acid (AA) as the modulator, UiO-66(AA) was synthesized. The
as illustrated in Figure 1. After the removal of water molecule linker-to-modulator ratio in the obtained UiO-66(AA) elucidated
attached to the defective Zr, the active Lewis acid site is by 1H NMR is c.a. 1:0.3 (Table S6). XRD analysis (Figure S1) and
available to promote the reaction. Theoretical simulation was SEM images (Figure S3) reveal that UiO-66(AA) possesses better
employed to support this hypothesis. The results reveal that the crystalline structure, with larger particle size compared to the
defective UiO-66 is an effective catalyst providing Lewis acid site
(Zr4+) and OH that can facilitate the CC bond cleavage and the Table 1. Percentage of D-xylose conversion and yields of the
hydride shift with the activation energies of 10.40 and 24.01 two major products obtained when using different catalysts.
kcal mol-1, respectively (Figure S7).
Catalyst
% D-Xylose
conversion
52.94
LA
Furfural
(mol)
0.37
0.40
0.04
0.20
0.09
0.13
LA/
Furfural
0.08
1.38
12.77
5.87
The catalytic performance of UiO-66 was experimentally
investigated and compared to those of benchmark ZrO2 and
ZnO catalysts as well as the controlled experiment without an
addition of catalyst. Note that, ZrO2 possesses Zr4+ similar to
UiO-66 while ZnO has been reported as the most effective
catalysts for LA production from D-xylose.5c All the reactions
were carried out at 170 °C for 4 h, the optimum reaction
temperature and reaction time for LA production (Figure S13).
The results are summarized in Table 1. The product yields
reported in this study are calculated based on 1 mol of D-Xylose.
(mol)
0.03
0.55
0.45
1.17
0.76
1.14
No-catalyst
ZrO2
ZnO
UiO-66
UiO-66(AA)
UiO-66(AA)*
77.84
99.55
98.26
98.50
8.44
8.99
98.00
Reaction conditions: initial D-xylose 0.45 g (3 mmol), catalyst 0.25 g, N2
pressure of 15 bar, at 170°C-4h in batch reactor. The reactions were
performed at least 3 times. Mol products of LA and furfural were
calculated based on 1 mol of D-xylose.
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Journal Name
ARTICLE
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DOI: 10.1039/D0CC03424J
Defect-free
Defective
Figure 2. (a) Illustrations of defect-free and defective inorganic nodes used in the EXAFS fitting, and the Zr K-edge EXAFS spectra of (b) UiO-
66, (c) UiO-66(AA) and (d) UiO-66(AA)*. Zr, Oµ3, OCOO, and OOH/H2O are shown in blue, orange, red, and black, respectively. FT of k-range: 3.0 -
12.5 Å-1 (3.0 - 12.0 Å-1 for UiO-66(AA)*) using k3-weighing. Fitting R-range: 1.15 - 4.2 Å.
pristine UiO-66. In addition, UiO-66(AA) presents larger of defective Zr(1) while UiO-66(AA) presents only 9%.
crystallite sites as seen from the narrower full width at half Additionally, the smaller particle size of UiO-66 as observed in
maximum (FWHM) of the major PXRD peak. The catalytic SEM images (Figure S3) facilitates the reactant diffusion to the
performance of UiO-66(AA) was examined, and the results are active site, and/or the product diffusion out from the active site.
shown in Table 1. In details, UiO-66(AA) exhibits the D-xylose Hence, the production of LA when using UiO-66 catalyst is
conversion of 98.50% which is comparable to that of UiO-66 enhanced by means of both the higher concentration of active
(98.26%). Interestingly, furfural was less produced, leading to sites Zr(1) and the smaller particle size, which results in the
the enhanced selectivity of LA over furfural (8.44) as compared higher LA yield.
to the UiO-66(AA) catalyst (5.87). However, the total yield of LA
from UiO-66(AA) is only 0.76 mol, which are lower than the case compared to the UiO-66, it significantly suppresses the
of UiO-66 (1.17 mol). formation of furfural to 0.09 mol (0.20 mol for the UiO-66). In
Even though the UiO-66(AA) produces less LA yield
To explain the distinct performances of UiO-66 and UiO- fact, the diffusion of the reactant (D-xylose) to the catalytic
66(AA), the local defect concentrations at the Zr nodes of each active sites within larger particles of the UiO-66(AA) should be
catalysts were examined by Zr K-edge extended X-ray slightly difficult and therefore affects the formation of LA.
absorption fine structure (EXAFS) analysis. Zr K-edge EXAFS However, the higher crystallinity of the larger-particles UiO-
spectra of UiO-66 and UiO-66(AA) together with the defect-free 66(AA) significantly influences the reduction of furfural
and defective model clusters employed in the fitting are formation. As a result, the selectivity of LA over furfural is
depicted in Figure 2. The details explanation of analysis was increased. In another case, the smaller-size and lower-
described in the Supporting information (Table S7 and Figure crystallinity UiO-66 catalyst may not provide only the desired Zr
S9). The defect model consists of one missing defects used for the LA production but also other undesired
(carboxylate)linker creating two defective Zr sites coordinating defects (e.g. missing metal, etc).14 These undesired defects
with OH and H2O denoted as Zr(1) which supply Lewis acid sites possibly cause the formation of furfural and consequently
and OH to promote the LA production. Note that, the defects reduce the selectivity of LA over furfural for D-xylose
created from the coordination with AA are considered as similar conversion.
as the ideal saturated Zr sites (not catalytically active Zr(1) site)
In order to increase LA yield and still maintain the high
since they have similar coordinated atoms (the carboxylate selectivity, the coordinated AA within the UiO-66(AA) should be
oxygen as the one of BDC linker) in the first shell scattering used removed to generate the catalytically active Zr(1) nodes which
in the fitting. The fitting results reveal that UiO-66 contains 14% are coordinated with OH and H2O. Accordingly, UiO-66(AA)
This journal is © The Royal Society of Chemistry 20xx
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3. (a) A. Chatterjee, X. Hu and F. L. Y. Lam, Catal. Today, 2018, 314,
was refluxed in DI water, denoted as UiO-66(AA)*. Based on the
1H NMR of the digested UiO-66(AA)*, only trace amount of AA
remains in the framework (Table S6). Notably, the activation
does not damage the crystallinity and the morphology of the
catalyst (Figure S1 and S3). Additionally, the removal of AA leads
to a significant increase of pore volume and specific surface area
(Figure S12). This enhances the excellent catalytic activity of
UiO-66(AA)* by overcoming the limitation in diffusion of the
reactant and the products to/from the large-particles UiO-
66(AA)*. The concentration of active Zr(1) sites increases to 24%
as shown in the results of EXAFS analysis (Figure 2 and S9). As
expected, catalytic performance of UiO-66(AA)* is markedly
improved, producing high LA yield of 1.14 mol while the high
selectivity attribute is maintained. Note, the slight increase in
furfural yield for UiO-66(AA)* to 0.13 mol is plausibly due to the
aid of Lewis acid in the conversion of D-xylose to furfural via
xylulose isomerization.15 Compared to the original UiO-66,
much lower amount of furfural was produced on UiO-66(AA)*.
The results signify the dominant role of surface phenomena on
MOF catalyst.
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129-136; (b) A. Herbst and C. Janiak, New J. Chem., 2016, 40, 7958-
DOI: 10.1039/D0CC03424J
7967; (c) J. Chen, K. Li, L. Chen, R. Liu, X. Huang and D. Ye, Green
Chem., 2014, 16, 2490-2499; (d) Y. Liu, C. Ma, C. Huang, Y. Fu and J.
Chang, Ind. Eng. Chem. Res., 2018, 57, 16628-16634; (e) D. L.
Burnett, R. Oozeerally, R. Pertiwi, T. W. Chamberlain, N. Cherkasov,
G. J. Clarkson, Y. K. Krisnandi, V. Degirmenci and R. I. Walton, Chem.
Commun., 2019, 55, 11446-11449.
4. (a) M. Yabushita, P. Li, T. Islamoglu, H. Kobayashi, A. Fukuoka, O.
K. Farha and A. Katz, Ind. Eng. Chem. Res., 2017, 56, 7141-7148; (b)
A. Dhakshinamoorthy, A. Santiago Portillo, A. M. Asiri and H. Garcia,
ChemCatChem, 2019, 11, 899-923; (c) N. Devarajan and P. Suresh,
New J. Chem., 2019, 43, 6806-6814; (d) Z. Miao, C. Qi, A. M.
Wensley and Y. Luan, RSC Adv., 2016, 6, 67226-67231.
5. (a) X. Yang, L. Yang, W. Fan and H. Lin, Catal. Today, 2016, 269,
56-64; (b) L. Yang, J. Su, S. Carl, J. G. Lynam, X. Yang and H. Lin, Appl.
Catal. B: Environ., 2015, 162, 149-157; (c) P. N. Paulino, O. C. Reis, Y.
E. Licea, E. M. Albuquerque and M. A. Fraga, Catal. Sci. Technol.,
2018, 8, 4945-4956; (d) B. Murillo, B. Zornoza, O. de la Iglesia, C.
Téllez and J. Coronas, J. Catal., 2016, 334, 60-67; (e) S. Huang, K. L.
Yang, X. F. Liu, H. Pan, H. Zhang and S. Yang, RSC Adv., 2017, 7,
5621-5627.
In summary, we demonstrated that defective Zr-based UiO-
66 can effectively produce LA from D-xylose via the
hydrothermal reaction. According to the different synthesis
methods, UiO-66 and UiO-66(AA) catalysts possess different
particle size and importantly different concentrations of active
sites on the defective Zr nodes. Possessing more local defective
sites, the UiO-66 produces high yield of LA, while the UiO-66(AA)
with better crystallinity shows high selectivity of LA over
furfural. The enhanced catalytic activity for both aspects
(extensively high LA yield and high selectivity) can be granted
from the novel UiO-66(AA)* catalyst. This important finding
clearly demonstrated that MOFs with the proper structural
design can be a prominent catalyst to produce LA from D-xylose.
This study additionally highlights that the designated function
of MOFs is splendidly flexible through the synthesis and design.
This work was supported by the Research Chair Grant 2017
(FDA-CO-2560-5655), the SPAIII–Integrated Platform: Bio-based
Materials (P1850012) from NSTDA, and NANOTEC, through its
program of Research Network of NANOTEC (RNN). The authors
acknowledge the support from VISTEC for postdoctoral and PhD
fellowships.
6. (a) P. Mäki Arvela, I. L. Simakova, T. Salmi and D. Y. Murzin,
Chem. Rev., 2014, 114, 1909-1971; (b) R. Datta and M. Henry, J.
Chem. Technol. Biotechnol., 2006, 81, 1119-1129; (c) S. Mecking,
Angew. Chem. Int. Ed., 2004, 43, 1078-1085.
7. (a) A. Corma, S. Iborra and A. Velty, Chem. Rev., 2007, 107,
2411-2502; (b) A. Onda, in Application of Hydrothermal Reactions to
Biomass Conversion, ed. F. Jin, Springer-Verlag Berlin Heidelberg,
2014, ch. 4, pp. 83-107.
8. (a) A. Onda, T. Ochi, K. Kajiyoshi and K. Yanagisawa, Catal.
Commun., 2008, 9, 1050-1053; (b) Y. Sun, L. Shi, H. Wang, G. Miao,
L. Kong, S. Li and Y. Sun, Sustain. Energ. Fuels., 2019, 3, 1163-1171;
(c) W. Dong, Z. Shen, B. Peng, M. Gu, X. Zhou, B. Xiang and Y. Zhang,
Sci Rep, 2016, 6, 26713.
9. S. Yamaguchi and T. Baba, Molecules, 2016, 21, 937.
10. J. H. Cavka, S. Jakobsen, U. Olsbye, N. Guillou, C. Lamberti, S.
Bordiga and K. P. Lillerud, J. Am. Chem. Soc., 2008, 130, 13850-
13851.
11. (a) F. Zhou, N. Lu, B. Fan, H. Wang and R. Li, J. Energy Chem.,
2016, 25, 874-879; (b) D. Yang, M. A. Ortuño, V. Bernales, C. J.
Cramer, L. Gagliardi and B. C. Gates, J. Am. Chem. Soc., 2018, 140,
3751-3759; (c) F. Vermoortele, B. Bueken, G. Le Bars, B. Van de
Voorde, M. Vandichel, K. Houthoofd, A. Vimont, M. Daturi, M.
Waroquier, V. Van Speybroeck, C. Kirschhock and D. E. De Vos, J.
Am. Chem. Soc., 2013, 135, 11465-11468; (d) C. Caratelli, J. Hajek, F.
G. Cirujano, M. Waroquier, F. X. Llabrés i Xamena and V. Van
Speybroeck, J. Catal., 2017, 352, 401-414.
Conflicts of interest
There are no conflicts of interest to declare.
12. H. Kishida, F. Jin, X. Yan, T. Moriya and H. Enomoto, Carbohydr.
Res., 2006, 341, 2619-2623.
Notes and references
13. (a) H. Wu, Y. S. Chua, V. Krungleviciute, M. Tyagi, P. Chen, T.
Yildirim and W. Zhou, J. Am. Chem. Soc., 2013, 135, 10525-10532;
(b) G. C. Shearer, S. Chavan, S. Bordiga, S. Svelle, U. Olsbye and K. P.
Lillerud, Chem. Mater., 2016, 28, 3749-3761; (c) W. Morris, S. Wang,
D. Cho, E. Auyeung, P. Li, O. K. Farha and C. A. Mirkin, ACS Appl.
Mater. Interfaces, 2017, 9, 33413-33418.
14. Y. Wang, L. Li, P. Dai, L. Yan, L. Cao, X. Gu and X. Zhao, J. Mater.
Chem. A, 2017, 5, 22372-22379.
15. V. Choudhary, S. I. Sandler and D. G. Vlachos, ACS Catal., 2012,
2, 2022-2028.
1. (a) Y. Kuwahara, H. Kango and H. Yamashita, ACS Sustain., 2017,
5, 1141-1152; (b) L. Ning, S. Liao, H. Cui, L. Yu and X. Tong, ACS
Sustain., 2018, 6, 135-142; (c) R. Fang, R. Luque and Y. Li, Green
Chem., 2016, 18, 3152-3157.
2. (a) Y. B. Huang, J. Liang, X. S. Wang and R. Cao, Chem. Soc. Rev.,
2017, 46, 126-157; (b) L. Zhu, X. Q. Liu, H. L. Jiang and L. B. Sun,
Chem. Rev., 2017, 117, 8129-8176; (c) A. Corma, H. García and F. X.
Llabrés i Xamena, Chem. Rev., 2010, 110, 4606-4655; (d) J. S. Qin, S.
Yuan, C. Lollar, J. Pang, A. Alsalme and H. C. Zhou, Chem. Commun.,
2018, 54, 4231-4249; (e) H. L. Jiang and Q. Xu, Chem. Commun.,
2011, 47, 3351-3370.
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