Microporous Polymeric Spheres as Highly Efficient and Metal-Free Catalyst for the Cycloaddition of CO2 to Cyclic Organic Carbonates at Ambient Conditions

Article abstract of DOI:10.1007/s10562-020-03206-y

Abstract: The cycloaddition of CO₂ with epoxides to cyclic organic carbonates using metal-free heterogeneous catalysts is considered as a 100percent atom-economic and environmental-friendly route for CO₂ utilization. Herein, we developed a metal-free microporous polymeric spheres catalyst (p-TBIB) by a simple Friedel–Crafts alkylation and applied in the cycloaddition of CO₂ to cyclic organic carbonates. The catalyst shows high CO₂ uptake (62.7?cm³?g^?1, at 298?K and 1?bar), high selectivity over N₂ (46 at 298?K) and perfect cycloaddition activities (66–97percent) and selectivities (over 99percent) and reusability (at least ten cycles) at ambient conditions (at 298?K and 1?bar). Graphic Abstract: [Figure not available: see fulltext.].

Full text of DOI:10.1007/s10562-020-03206-y

Catalysis Letters
https://doi.org/10.1007/s10562-020-03206-y
Microporous Polymeric Spheres as Highly Efcient and Metal‑Free
Catalyst for the Cycloaddition of CO2 to Cyclic Organic Carbonates
at Ambient Conditions
Shunmin Ding1 · Ling Sun1 · Xiaohua Ma1 · Dan Cheng1 · Shaohua Wu1 · Rong Zeng2 · Shengjun Deng1 · Chao Chen1 ·
Ning Zhang1
Received: 6 February 2020 / Accepted: 1 April 2020
© Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract
The cycloaddition of CO2 with epoxides to cyclic organic carbonates using metal-free heterogeneous catalysts is considered
as a 100% atom-economic and environmental-friendly route for CO2 utilization. Herein, we developed a metal-free micropo-
rous polymeric spheres catalyst (p-TBIB) by a simple Friedel–Crafts alkylation and applied in the cycloaddition of CO2 to
cyclic organic carbonates. The catalyst shows high CO2 uptake (62.7 cm3 g−1, at 298 K and 1 bar), high selectivity over N2
(46 at 298 K) and perfect cycloaddition activities (66–97%) and selectivities (over 99%) and reusability (at least ten cycles)
at ambient conditions (at 298 K and 1 bar).
Graphic Abstract
Keywords Carbon dioxide · Cyclic organic carbonates · Heterogeneous catalysis · Microporous polymeric spheres · Metal-
free
1 Introduction
Electronic supplementary material The online version of this
Carbon dioxide (CO2) emission is widely recognized as a
article (https://doi.org/10.1007/s10562-020-03206-y) contains
main cause of greenhouse efect that leads to global warm-
ing. Concurrently, it is also regarded as an attractive renew-
able carbon resource with abundant, nontoxic, cheap, and
nonflammable nature [1–3]. In recent years, numerous
pioneering studies have been undertaken on the utilization
of CO2 to high-value organic products. In terms of “envi-
ronmental-friendly chemistry” and “atom economy”, the
cycloaddition of CO2 with epoxides is a promising route to
supplementary material, which is available to authorized users.
* Shunmin Ding
dingshunmin2007@163.com
* Rong Zeng
zengrongnc@163.com
* Chao Chen
chaochen@ncu.edu.cn
Extended author information available on the last page of the article
Vol.:(0123456789)
1 3

S. Ding et al.
produce cyclic organic carbonates, which are widely used as
aprotic polar solvents, electrolytes, monomers for polymers,
fne chemical intermediates, etc. [4–6].
‒NH) can activate epoxides by hydrogen bond, and facili-
tating ring opening and subsequent CO2 insertion [32–36].
Although the ‒OH and ‒NH can easily open the ring of
epoxides, most of them require high temperature or pres-
sure due to the low CO2 concentration in the liquid phase.
Therefore, how to improve CO2 concentration in the reac-
tion system and the epoxides ring opening ability is the two
aspect of designing a high catalyst for the reaction.
In the past decades, numerous homogeneous catalysts
[5–15] such as organocatalysts [5, 7, 8], metal salen com-
plexes [6, 9–11] and metalloporphyrins complexes [12–15]
are developed for this purpose. Although some of them
exhibit high activities for the reaction, the catalysts are
not easily separated from the catalytic system and reused.
To solve the drawback, heterogeneous catalysts especially
porous materials based heterogenous catalysts [16–24], such
as nanoporous polymers, nanoporous polymers metalled
catalysts and metalorganic frameworks (MOFs) have been
developed. Though the heterogeneous catalysts are ease of
purifcation and recycle, most of them perform under rigor-
ous temperatures, drastic CO2 pressures. Only a few het-
erogeneous catalysts [17–23] (Co/POP-TPP [17], Co(III)@
cage [18], Hf-NU-1000 [19], Cu-MOF [20–22] and Co-
CMP [23]) have the ability for converting CO2 into cyclic
carbonates under mild conditions such as at room tempera-
ture and atmospheric pressure, which typically need metal
ions (e.g. Cu2+ and Co2+). However, the metal ions can be
leached into the catalytic system to pollute the products.
Hence, developing novel, stable and highly efcient metal-
free heterogeneous catalysts for the cycloaddition of CO2
with epoxides under mild and even ambient conditions is
still a big challenge.
Herein, we design and synthesize a 1,3,5-tris(1H-
benzo[d]imidazol-2-yl)benzene-linked polymeric spheres
catalyst (p-TBIB, Scheme 1) with imidazole units (con-
taining –NH bonds), high CO2 capacity of 100.8 cm3 g−1
(62.7 cm3 g−1) and CO2/N2 selectivity of 37 (46) under 1 bar
at 273 K (298 K), respectively. As expected, the catalyst
exhibits very good conversions and cyclic organic carbon-
ates yields under ambient conditions with a perfect reus-
ability (at least ten cycles).
2 Experimental
2.1 Materials
All starting materials and solvents, unless otherwise noted,
were obtained from Acros Organics and used without fur-
ther purifcation. Trimesic acid, 1,2-diaminobenzene were
purchased from Adamas and used without further purifca-
tion. Phosphoric acid was purchased from Damao Chemical
Regents Co. Ltd. Dichloromethane and aluminum chlorides
were purchased from Sinopharm Chemical Regents Co. Ltd.
The dichloromethane was dried over CaH2 and freshly dis-
tilled prior to use.
In industrial production, cyclic carbonates are prepared
under high CO2 pressure (5 MPa) to ensure adequate CO2
reaction concentration [25]. In general, the CO2 concentra-
tion of CO2 emission is lower than 15% [26]. So the CO2
capacity and selectivity of a catalyst is one of the key fac-
tors to the reaction rate for the cycloaddition of CO2 with
epoxides. Recently, Porous organic polymers (POPs) have
been focused on as an ideal CO2 absorbent because of their
large specifc surface areas, high pore volumes, and abun-
dant functional groups. The POPs including covalent organic
frameworks (COFs) [27, 28], conjugated microporous poly-
mers (CMPs) [29] and hyper-crosslinked polymers (HCPs)
[30] usually show high CO2 capacity and selectivity. The
stability of the POPs is one of the most important aspects
for their industrial applications such as in catalysis and CO2
selective capture. Various nanostructured POPs have been
synthesized. Among them, spherical POPs have attracted
tremendous attention over the past decade. Because objects
in nature tend to approach minimum energy, spherical struc-
ture is one of the most perfect structures for matter, having
the smallest surface-to-volume ratio, which is an optimal
shape by nature selection [31].
2.2 Synthesis of 1,3,5‑tris(1H‑benzo[d]
imidazol‑2‑yl)benzene (TBIB)
We modifed the synthesis process of the literature [37]. The
detail procedure was given in supporting information.
2.3 Synthesis of 1,3,5‑tris(1H‑benzo[d]
imidazol‑2‑yl)benzene‑linked polymeric
spheres (p‑TBIB)
Under N2 gas protection, TBIB (200 mg, 0.47 mmol) was
dissolved in anhydrous dichloromethane (10 mL). The solu-
tion was subsequently added dropwise to a mixture of anhy-
drous AlCl3 (400 mg, 3.00 mmol) and anhydrous dichlo-
romethane (20 mL). The resulting mixture was heated to
80 °C and kept string under N2 atmosphere for 24 h. After
the reaction completed, it was cooled and quenched with
methanol (10 mL) in an ice-water bath. The obtained poly-
mer was washed with ethanol, 5% HCl, and DI-water. The
solid was further purifed using Soxhlet extraction with
To design a perfect POPs catalyst for the cycloaddition of
CO2 with epoxides with high activity, the selection of active
moieties is the key. In previous works, the active moieties
such as containing hydrogen bond donor groups (e.g., ‒OH,
1 3

Microporous Polymeric Spheres as Highly Efcient and Metal‑Free Catalyst for the Cycloaddition…
Scheme 1. The synthetic route to p-TBIB
methanol for 24 h and then with tetrahydrofuran for another
24 h. Finally, the desired tawny polymer was collected and
dried in a vacuum oven at 80 °C overnight. For comparison,
PTPB was prepared with the same method.
to the measurement, p-TBIB was dried at 393 K under high
vacuum (0.1 Pa) for 48 h. Isosteric heat of CO2 adsorption
(Qst) was calculated according to the Clausius–Clapeyron
equation by ftting CO2 isotherms (273 and 298 K) with
virial equation.
2.4 Characterization
2.6 Catalytic cycloaddition of CO2 with epoxides
Nitrogen sorption was measured on a Micro ASAP 2020
adsorption instrument at 77 K. FT-IR spectra were recorded
on a Nicolet 5700 instrument. X-ray difraction (XRD) meas-
urements were performed on a XD-3 difractometer with Cu
Kα radiation (λ=0.15418 nm, 40 kV/30 mA) at a scanning
step of 2° min−1. Thermogravimetric analysis (TGA) was
carried out using a TA Instruments Q-5000IR series thermal
gravimetric analyzer with samples under nitrogen at a heat-
ing rate of 10 °C min−1. X-ray photoelectron spectroscopy
(XPS) was performed on an ESCALAB250xi spectrometer
(Thermon Scientifc), all binding energies were calibrated
by using the C 1s peak at 284.8 eV as a reference. 1HNMR
spectra were recorded on an Agilent 400 MHz instrument
using TMS as the internal standard. Cross polarized magic
angle spinning (CP/MAS) solid state nuclear magnetic
resonance (SSNMR) spectrum was recorded using Bruker
Avance III-500 spectrometer. Scanning electron microscope
(SEM) images were collected on a Zeiss Auriga Crossbeam
SEM at an acceleration voltage of 5 kV.
In a typical reaction, a mixture of epoxide (5 mmol), tetrabu-
tylammonium bromide (TBAB) (37.5 mg 2.34 mol% relative
to epoxide), n-dodecane (1 mL, 4.48 mmol, internal stand-
ard) and catalyst (5 mg 0.819 mol% relative to epoxide) was
stirred at room temperature in a 10 mL round-bottomed fask
equipped with CO2 balloon (1 bar pure CO2 or 15% CO2
mixed with 85%N2). After reaction, the catalyst was sepa-
rated and the resulting solution was further diluted with ethyl
acetate. The reactants conversions (using internal standard
method) and products yields (measured by standard products
samples) were determined by a gas chromatography (Agi-
lent 7890B) equipped with a fame ionization detector and
a capillary column (HP-5, 30 m×0.25 mm×0.25 μm). The
typical conditions were as follows: injection temperature at
220 °C; detection temperature at 240 °C, column tempera-
ture at 60 °C for 2 min in the beginning, a ramp of 10 °C
min−1 to 220 °C and holding at 220 °C for 5 min.
For recycling tests, the reaction was carried out with
propylene oxide (40 mmol), tetrabutylammonium bro-
mide (TBAB) (300 mg, 2.34 mol% relative to epoxide),
n-dodecane (8 mL, internal standard) and catalyst (40 mg,
0.819 mol% relative to epoxide). After reaction, the catalyst
was separated by fltration, washed with EtOAc and CH2Cl2
2.5 CO2 and N2 adsorption
CO2 and N2 adsorption isotherms at 273 and 298 K were
also measured on a Micromeritics ASAP 2020 system. Prior
1 3

S. Ding et al.
Fig. 1. 13C CP/MAS NMR
spectra of p-TBIB Asterisk (*)
denotes spinning side band
(spinning speed=7.5 kHz)
for three times, respectively and dried d at 80 °C overnight
under vacuum. Then, the catalyst was used for the next run
with addition of fresh TBAB and propylene oxide.
[37]. Then, 1,3,5-tris(1H-benzo[d]imidazol-2-yl)benzene
was dissolved in anhydrous dichloromethane and polymer-
ized by a facile Friedel–Crafts alkylation using anhydrous
AlCl3 as catalyst. As the procedure shown in Scheme 1, the
1,3,5-tris(1H-benzo[d]imidazol-2-yl)benzene molecules can
be easily bending to polymeric spheres (p-TBIB) under the
polymerization process.
3 Results and discussion
Firstly, we synthesized 1,3,5-tris(1H-benzo[d]imidazol-2-yl)
benzene monomer by condensation of trimesoic acid and
o-phenylenediamine (Scheme S1). The monomer was con-
frmed by 1H-NMR (Fig. S1), 13CNMR (Fig. S2) and high
resolution mass spectrometry (Fig. S3), the characterization
results are agreement with those of reported in literature
We subsequently performed the 1H–13C cross-polariza-
tion magic-angle spinning (CP-MAS) 13C NMR spectra to
study the structure features at the molecular level (Fig. 1).
The peak at ca.150.4 ppm (c) in p-TBIB, correspond to
NC(Ph)N in benzimidazole units. The existence of aromatic
carbons can be confrmed by the peaks at ca.114.7 (e), 126.8
Fig. 2 a N2 adsorption–desorption isotherms with pore size distributions and b SEM image of p-TBIB
1 3

Microporous Polymeric Spheres as Highly Efcient and Metal‑Free Catalyst for the Cycloaddition…
Fig. 3 a CO2/N2 uptake isotherms of p-TBIB at both 273 K and 298 K, up to 1 bar; b N 1s XPS spectra of p-TBIB
(a) and 133.2 ppm (b, d and f) [38]. More importantly, the
chemical shift at ca.37.2 ppm is assigned to the methylene
carbon [38]. demonstrating the monomer linked like the
drawing structure in Fig. 1 and Scheme 1. The existence of
free N–H bond can be further evidenced by FT-IR spectra
(Fig. S4) at 3415 cm−1 both in TBIB monomer and p-TBIB
[38].
cm3 g−1 of N2 could be adsorbed. The CO2/N2 selectivity
was then calculated to be as high as 37 (46) at 273 K (298 K)
and 1 bar from the ratio of the initial slopes (Table S1 and
Fig. S6), comparable with that of benzimidazole-linked
polymers BILP-X (1–7) (31–71 at 298 K) [38] and many
Table 1 The cycloaddition of CO2 with propylene oxide
catalyzed by various catalysts at ambient conditions
To deeper understand the physical structure of synthe-
sized p-TBIB, N2 adsorption–desorption, powder X-ray dif-
fraction (PXRD) and Scan electron microscopy (SEM) were
measured. N2 adsorption–desorption isotherm of p-TBIB
(Fig. 2a) was frstly recorded at −77 K to assess its porous
nature. The p-TBIB shows typical type-I isotherm with high
N2 uptake at low relative pressure and high abundance of
micropores calculated by the nonlocal density functional
theory (NLDFT) (< 2 nm). The p-TBIB exhibits a high
Brunauer–Emmett–Teller (BET) surface area of 840 m2 g−1
and total pore volume and 1.20 cm3 g−1 (Table S1), respec-
tively. p-TBIB was obtained as an amorphous powder,
evidenced by both PXRD pattern (Fig. S5). But the mor-
phology of p-TBIB displayed in SEM image (Fig. 2b) is
spherical shape with the size estimated to be ca. 1.0 μm. This
microporous and spherical polymer usually shows a high gas
capture and structural stability due to its high microporosity
and optimal shape of nature selection, which further proved
by the results of CO2 uptake and TG curves and solvent dis-
solving experiment, respectively.
Catalyst
Cocat
Conv. (%) Selec. (%) TONa Ref
–
–
–
0
39
0
38
52
96
45
97
95.6
58
–
>99
–
>99
97
98
>99
>99
99
>99
>99
–
–
–
–
This work
This work
This work
This work
TBAB
–
TBAB
–
TBAB
–
TBAB
PTBP
PTBP
TBIB
TBIB
p-TBIB
p-TBIB
215.5 This work
181.8 This work
110.0 This work
237.0 This work
433.5 [17]
175.7 [18]
25
Co/POP-TPP TBAB
Co(III)@cage TBAB
Hf-NU-1000 H4TBAPy 100
[19]
(Cr)
The material (p-TBIB) is capable of adsorbing a signif-
cant amount of CO2 molecules under the ambient condition.
The CO2 adsorption isotherms were carefully measured up
to 1 bar. As shown in Fig. 3a, the polymer shows uptake
capacities as high as 100.8 and 62.7 cm3 g−1 at 273 and
298 K, respectively. Selectivity is another important param-
eter for separation applications. In this regard, we further
measured N2 adsorption at 273 K (298 K) to examine the
separation ability of p-TBIB (Fig. 3a). Only 4.95 (2.0)
FJI-H7(Cu)
MMPF-9(Cu) TBAB
MMCF-2(Cu) TBAB
TBAB
66.5
87.4
95.4
81.5
99
99
99
99
332.5 [20]
699.2 [21]
756
167
[22]
[23]
Co-CMP
TBAB
Reaction conditions: propylene oxide and CO2 (1 bar) at 298 K for
24 h
aTON=molar of product/molar of catalyst
1 3

S. Ding et al.
Table 2 The cycloaddition of CO2 with various epoxides over the p-TBIB catalyst
Entry
1
epoxide
product
Conv. (%)
95 (24 h)
Select. (%)
>99
Yield (%)
95
TON
232.2
2
3
4
5
6
7
97 (24 h)
93 (24 h)
89 (24 h)
81 (96 h)
73 (96 h)
66 (96 h)
>99
>99
>99
>99
>99
>99
97
93
89
81
73
66
237.0
227.2
217.4
197.8
178.4
161.2
Reaction conditions: epoxide (5 mmol), p-TBIB catalyst (5 mg, 0.410 mol%), TBAB (37.6 mg, 2.34 mol%), at 298 K and 1 bar CO2
other porous organic polymers-based adsorbents [39–41].
We reasoned that high abundance of N-doped sites within
the polymeric backbone could play a crucial role in achiev-
ing this high selective CO2 adsorption performance. As a
result, we carried out the X-ray photoelectron spectroscopy
(XPS) in an efort to gain a better understanding of these
CO2-philic sites (Fig. 3b). To our delight, a high N doping of
14.49 at.% (Table S1) on the surface of the framework was
measured, where pyridinic (398.5 eV, 49.7%) and pyrrolic
nitrogen (400.5 eV, 50.3%) were the two diferent nitrogen
species [42]. Accordingly, they may serve as binding sites
for CO2 uptake through an electrostatic interaction, and thus
highly selective separation performance. The isosteric heats
of adsorption (Qst) on p-TBIB was also calculated by ftting
the CO2 adsorption isotherms obtained at 273 and 298 K and
by applying a variant of the Clausius–Claperyron equation
(Fig. S7). At low adsorption values, the polymer exhibits
a high adsorption heat of ca. 27 kJ mol−1, which could be
attributed to the existence of rich micropores and N-doped
CO2-philic sites [42].
The enrichment of the CO2 (62.7 cm3 g−1 at 298 K and
1 bar) and N-doped CO2-philic sites in the nanopores is
expected to be benefcial for the promotion of the CO2 con-
version. The cycloaddition of pure CO2 (1 bar) with propyl-
ene oxide (PO) at room temperature (298 K) was selected
as a model to start our exploratory experiments. As shown
in Table 1. Obviously, no reaction occurred in the absence
of any catalyst or with the no imidazole polyemer (1,3,5-tri-
phenylbenzene-linked polymer, PTPB) [43]. Compare
to PTPB, the p-TBIB displayed a higher propylene oxide
1 3

Microporous Polymeric Spheres as Highly Efcient and Metal‑Free Catalyst for the Cycloaddition…
Fig. 4 The reusablity of p-TBIB
in the cycloaddition of CO2
with propylene oxide (PO)
conversion (45%, TON: 110.0) and cycloaddition product
selectivity (99%). Besides, after the cocatalyst TBAB addi-
tion, the conversion increased from 45 to 97% (TON: 237.0),
while the conversion of only using the cocatalyst TBAB was
39%. These results indicated that amino-containing electro-
philes could interact with the epoxide via hydrogen bond-
ing interaction, thus facilitating the ring opening of propyl-
ene oxide. Moreover, the catalytic performance of p-TBIB
is completely comparable with that of the homogeneous
TBIB catalyst and near that of the most active metalated
heterogeneous catalysts (Co/POP-TPP [17], Co(III)@cage
[18], Hf-NU-1000 [19], Cu-MOF [20–22] and Co-CMP
[23]) with the assistant of cocatalyst at ambient conditions.
According to the achieved results, a reaction mechanism
(Scheme S2) is proposed, the p-TBIB frst react with PO via
hydrogen bonding interaction and then with the assistant of
cocatalyst to open the ring. Meanwhile, CO2 are absorbed
and activated on p-TBIB. Finally, the product is formed, the
catalyst returns to the original state.
vol. N2) should be more signifcant than that under pure
CO2. Unexpectedly, p-TBIB exhibited a higher catalytic per-
formance than that of homogeneous TBIB with or without
cocatalyst (Table S2), which was beneft from the high CO2
capacity and selectivity of p-TBIB.
The reusability and stability were the most important per-
formance for an ideal heterogeneous catalyst. The catalyst
p-TBIB can be reused at least ten times without any signif-
cant catalytic activity (over 90%) decrease. (Fig. 4) And the
structure was stable under nitrogen atmosphere up to 400 ℃
(Fig. S8) and in many solvents such as ethanol, acetone,
DMSO and propylene oxide (Fig. S9).
4 Conclusions
In summary, a metal-free microporous polymeric spheres
catalyst was developed by a simple Friedel–Crafts alkyla-
tion. The experimental results demonstrated that the high
CO2 uptake (62.7 cm3 g−1, at 298 K and 1 bar), selectivity
over N2 (46 at 298 K) and the hydrogen bonding interaction
with the epoxides of the catalyst can boost the cycloaddi-
tion performance under ambient conditions even at ambient
conditions. More importantly, the high stable and reusability
of the catalyst are beneft from the spherical structure of
p-TBIB. Besides, the size-dependent catalysis also afects
the catalytic performance. According to the achieved results,
they might ofer the opportunity to design more efcient het-
erogeneous catalysts under ambient conditions for chemical
fxation of CO2 in the future.
Motivated by these promising catalytic results under
ambient conditions, the catalyst p-TBIB was extended to a
scope of epoxides substrates (Table 2). This catalyst is still
active for the conversion of these epoxides (conversions:
66–97%, TON numbers: 161.2–237.0), but the activities
are strongly dependent on their structures. Clearly, size-
dependent catalysis is observed when using the substrates
with larger dimensions (Table 2, entries 5–7) which give rise
to lower activities.
Due to the emission of CO2 in industrial processes nor-
mally below 15% [26], the cycloaddition was carried out
under relatively low CO2 concentration (15%vol. CO2 +85%
1 3

S. Ding et al.
20. Zheng J, Wu M, Jiang F, Su W, Hong M (2015) Chem Sci 6:3466
21. Gao W, Wojtas L, Ma S (2014) Chem Commun 50:5316
22. Gao W, Chen Y, Niu Y, Williams K, Cash L, Perez PJ, Wojtas L,
Cai J, Chen Y, Ma S (2014) Angew Chem Int Ed 53:2615
23. Xie Y, Wang T, Liu X, Zou K, Deng W (2013) Nat Commun 4:1
24. Bondarenko GN, Dvurechenskaya EG, Ganina OG, Alonso F,
Beletskaya IP (2019) Appl Catal B 254:380
Acknowledgements This work supported by the National Natu-
ral Science Foundation of China (No. 21663016), the Key Labora-
tory of Jiangxi Province For Environment and Energy Catalysis (No.
20181BCD40004), the research project on teaching reform of degree
and graduate education of Jiangxi Province (No. JXYJG-2018-007),
the project of East China University of Technology of experimental
technology research and development (No. DHSYKF-2019-024) and
the Opening Project of Jiangxi Province Key Laboratory of Polymer
Micro/Nano Manufacturing and Devices (No. PMND201906).
25. Yu S, Liu X, Ma J, Niu Z, Cheng P (2016) J CO2 Util 14:122
26. Bae YS, Snurr RQ (2011) Angew Chem Int Ed 50:11586
27. Ding S, Wang W (2013) Chem Soc Rev 42:548
28. Feng X, Ding X, Jiang D (2012) Chem Soc Rev 41:6010
29. Dawson R, Adams DJ, Cooper AI (2011) Chem Sci 2:1173
30. Tan L, Tan B (2017) Chem Soc Rev 46:3322
31. Qiu P, Ma B, Hung C, Li W, Zhao D (2019) Acc Chem Res
52:2928
References
1. Zhang L, Zhao Z, Gong J (2017) Angew Chem Int Ed 56:11326
2. Eveloy V (2019) Renew Sust Energ Rev 108:550
3. Yang ZZ, He LN, Gao J, Liu AH, Yu B (2012) Energy Environ
Sci 5:6602
32. Zhang W, Mei Y, Wu P, Wu H, He M (2019) Catal Sci Technol
9:1030
33. Steinbauer J, Werner T (2017) Chemsuschem 10:3025
34. Wang T, Song X, Luo Q, Yang X, Chong S, Zhang J, Ji M (2018)
Microporous Mesoporous Mater 267:84
4. Omae I (2012) Coord Chem Rev 256:1384
5. Munirah MZ, Abdul RM (2018) Renew Sust Energ Rev 98:56
6. Lu X, Darensbourg DJ (2012) Chem Soc Rev 41:1462
7. Li Y, Cui D, Zhu J, Huang P, Tian Z, Jia Y, Wang P (2019)
Green Chem 21:5231
35. Sun J, Wang J, Cheng W, Zhang J, Li X, Zhang S, She Y (2012)
Green Chem 14:654
36. Zhang W, Wang Q, Wu H, Wu P, He M (2014) Green Chem
16:4767
8. Zhang S, Sun J, Zhang X, Xin J, Miao Q, Wang J (2014) Chem
Soc Rev 43:7838
37. Xiong J, Li J, Mo G, Huo J, Liu J, Chen X, Wang Z (2014) J Org
Chem 79:11619
9. Paddock RL, Nguyen ST (2001) J Am Chem Soc 123:11498
10. Lu X, Zhang Y, Jin K, Luo L, Wang H (2004) J Catal 227:537
11. Wu X, North M (2017) Chemsuschem 10:74
12. Ema T, Miyazaki Y, Koyama S, Yano Y, Sakai T (2012) Chem
Commun 48:4489
38. Rabbani MG, El-Kaderi HM (2012) Chem Mater 24:1511
39. Zhu X, Ding S, Abney CW, Browning KL, Sacci RL, Veith GM,
Tian C, Dai S (2017) Chem Commun 53:7645
40. Zhu X, Tian C, Jin T, Browning KL, Sacci RL, Veith GM, Dai S
(2017) ACS Macro Lett 6:1056
13. Ema T, Miyazaki Y, Shimonishi J, Maeda C, Hasegawa J (2014)
J Am Chem Soc 136:15270
41. Zhu X, Tian C, Jin T, Wang J, Mahurin SM, Mei W, Xiong Y, Hu
J, Feng X, Liu H (2014) Chem Commun 50:15055
42. Zhu X, Tian C, Veith GM, Abney CW, Dehaudt J, Dai S (2016) J
Am Chem Soc 138:11497
14. Qin Y, Guo H, Sheng X, Wang X, Wang F (2015) Green Chem
17:2853
15. Maeda C, Taniguchi T, Ogawa K, Ema T (2015) Angew Chem
Int Ed 54:134
43. Xu S, Luo Y, Tan B (2013) Macromol Rapid Commun 34:471
16. Liang J, Huang Y, Cao R (2019) Coord Chem Rev 378:32
17. Dai Z, Sun Q, Liu X, Bian C, Wu Q, Pan S, Wang L, Meng X,
Deng F, Xiao FS (2016) J Catal 338:202
Publisher’s Note Springer Nature remains neutral with regard to
jurisdictional claims in published maps and institutional afliations.
18. Ng CK, Toh RW, Lin TT, Luo H, Hor TA, Wu J (2019) Chem Sci
10:1549
19. Beyzavi MH, Klet RC, Tussupbayev S, Borycz J, Vermeulen NA,
Cramer CJ, Stoddart J, Hupp JT, Farha OK (2014) J Am Chem
Soc 136:15861
Afliations
Shunmin Ding1 · Ling Sun1 · Xiaohua Ma1 · Dan Cheng1 · Shaohua Wu1 · Rong Zeng2 · Shengjun Deng1 · Chao Chen1 ·
Ning Zhang1
1
2
Key Laboratory of Jiangxi Province for Environment
and Energy Catalysis, College of Chemistry,
Nanchang University, Nanchang 330031, Jiangxi,
People’s Republic of China
Jiangxi Province Key Laboratory of Polymer Micro/Nano
Manufacturing and Devices, School of Chemistry, Biology
and Materials Science, East China University of Technology,
Nanchang 330013, People’s Republic of China
1 3