Synthesis of nitrogen and sulfur co-doped hierarchical porous carbons and metal-free oxidative coupling of silanes with alcohols

Article abstract of DOI:10.1039/c7cc07931a

Hierarchically porous N and S co-doped carbon was prepared by using 2,5-dihydroxy-1,4-benzoquinone as the carbon source, thiourea as the N and S source, and SiO₂ particles as the template. Using the material as the catalyst, oxidative coupling of silanes with alcohols was conducted for the first time under metal-free conditions.

Full text of DOI:10.1039/c7cc07931a

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Synthesis of Nitrogen and Sulfur Co-doped Hierarchical Porous
Carbons and Metal-free Oxidative Coupling of Silanes with
Alcohols
Received 00th January 20xx,
Accepted 00th January 20xx
a
b
a
a
a
*
b
DOI: 10.1039/x0xx00000x
Bingfeng Chen, Fengbo Li, Qingqing Mei, Youdi Yang, Huizhen Liu, and Guoqing Yuan,
a*
Buxing Han
www.rsc.org/
Hierarchically porous N and S co-doped carbon was prepared advantages of the pores of different sizes in diffusion and
8
using 2,5-dihydroxy-1,4-benzoquinone as the carbon source, adsorption of the species in the reaction systems. Synthesis
2
thiourea as N and S source, and SiO particles as the template. and application of this class of catalytic materials have
Using the material as the catalyst, oxidative coupling of silanes received much attention. In this work, we developed a route to
with alcohols was conducted for the first time at metal-free prepare hierarchically porous N and S co-doped carbon
condition.
(HPNSC) using 2,5-dihydroxy-1,4-benzoquinone as the carbon
source and thiourea as the source of N and S dopants, and SiO
2
Carbon materials are promising substitutes for metal materials
in some important applications due to their earth-abundant
feedstocks, high specific surface area, corrosion resistance and
readily tuneable properties through surface modification or
particles of different sizes were used as the templates for the
mesopores and macropores. The as-prepared HPNSC was very
efficient catalyst for the oxidative etherification of silanes with
alcohols. To the best of our knowledge, this is the first metal-
free catalytic system for this kind of reactions, although many
1
heteroatom doping. Heteroatom doping modifies geometric
9
and electronic structures of carbon materials, and introduces
1
metallic catalysts have been reported.
a
catalytic active sites. In recent years, heteroatom doped
carbon materials have attracted much attention, and many
The route to prepare the HPNSC is shown schematically in
Scheme 1. In the experiments, the 2, 5-dihydroxy-1, 4-benzo-
quinone (carbon source) and thiourea (N and S source) were
2
functional carbon materials, such as N-doped, S-doped, and
3
4
P-doped carbon materials, have been reported.
mixed and heated to 150 °C to get the liquid solution. Then
SiO spheres of 180-220 nm (Figure S1a) and colloidal SiO2
Multiple doping is a versatile approach for developing
functional carbon materials and regulating properties of
carbon by synergistic effect of dopants. Carbon materials co-
doped with two or more kinds of heteroatoms have also been
reported as catalytic materials. For example, S, N co-doped
carbon nanotubes prepared by using CdS as template has been
2
nanoparticles of about 10 nm (Figure S1b) were added into the
solution and were dispersed uniformly in the solution after
stirring. Then the mixture underwent pyrolysis at 900 °C and
acid etching process to remove template to obtain the HPNSC.
Similar procedure has been adopted for synthesis hierarch-
ically porous N-doped carbon (HPNC) using 2,5-dihydroxy-1,4-
benzoquinone and urea as precursors. For comparison, N and
S co-doped porous carbon material was synthesized by using
hard template (SBA-15), which is labelled as NSPC-SBA.
5
reported in catalytic reduction of p-nitrophenol. N and S co-
doped nanoporous graphene showed high catalytic activities
towards hydrogen evolution reaction, which was synthesized
6
by nanoporous Ni-based chemical vapor deposition. Meng et
al. showed that N, O and S-tridoped polypyrrole-derived nano-
7
porous carbons were active for alcohol oxidation reaction.
The morphology and structure for the as-synthesized HPNSC
are investigated by FE-SEM and TEM. As shown in Fig. 1a-c, the
Hierarchically porous catalysts usually show excellent
performance for different reactions because they integrate the
Scheme 1 Schematic demonstration of the route to prepare
the HPNSC.
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HPNSHC possessed hierarchical structure composed of (yellow), sulfur (purple), carbon (red), oxygen (blue) of the
mesopores (10 nm) templated from colloidal SiO nanoparticle HPNSC.
and macropores (180-220 nm) derived from silica spheres,
which were consistent with the size of the SiO templates
used. The N adsorption-desorption isotherm of the HPNSC
2
2
2
exhibited a type-IV curve with a hysteresis, indicating the
existence of mesopores (Fig.1d). The mesopore size
2
distribution obtained from N adsorption-desorption isotherm
centred at 7.8 nm as shown in Fig 1e, which was reasonably
consistent with the mesopores observed (Fig 1b). The BET
p
surface area (SBET) and total pore volume (V ) of the material
2
-1
3 -1
were 866 m g and 1.47 cm g , respectively. NSPC-SBA display
type-IV isotherms with an H1 hysteresis loop (Fig. S2a),
2
characteristic of mesoporous materials (S : 698 m g ; V :
-1
BET
p
3
.41 cm g ). This result is verified by TEM image (Fig. S2b) that
-1
0
NSPC-SBA was an inverse replica of the SBA-15 template. The
presence of heteroatoms in the HPNSC was verified by high
angle annular dark-field scanning TEM (HADDF-STEM) image Fig. 2 High resolution XPS spectra of N 1s (a), S 2p (b) and C 1s
coupled with the corresponding energy-dispersive X-ray (c) of the HPNSC material, and its schematic structure (d).
spectroscopy (EDX) elemental mapping images, which showed
the homogeneous distribution of C, N, S, and O across the eV), pyrrolic-N (N-5, 399.8 eV), graphitic-N (N-Q, 400.8 eV),
1
1
selected region (Fig 1f). This may favour the (electro) catalytic and pyridine N-oxide (N-Ox, 402.7 eV). The S 2p spectra (Fig.
1
0
performance.
2b) visualize the presence of two forms of S, carbon-bonded
The composition and chemical state of the N and S co-doped thiophene-like sulfur (C-S-C, 163.5/164.7 eV) and oxidized
1
carbon were elucidated by X-ray photoelectron spectroscopy sulfur species (C-SO -C (x=2-4), 167.4/168.6 eV). As shown in
2
X
(XPS) analysis (Fig. S3). According to elemental analysis, the Fig. 2c, the C 1s spectra can be fitted into several peaks
contents of N, S, C, H in HPNSC were 6.5%, 9.9%, 65.1%, and corresponding to C-C/C=C (284.5 eV), C-O/C-N (285.6 eV), C=O
1
.2%, respectively. The N 1s spectra (Fig. 2a) are deconvoluted (287.7 eV) and O-C=O (289.4 eV) species. Therefore, the XPS
3
1
into four different types of N species: pyridinic-N (N-6, 397.9
analysis further confirms that the heteroatoms are successfully
incorporated into the carbon framework of HPNSC.
XRD and Raman analysis were carried out to study the
carbon material. The material showed a broad peak in the
range of 20-30° (Fig. S4), indicating that a carbon framework
with partial graphitization was formed. Raman spectra of the
HPNSC showed two typical vibration bonds of carbon materials
-
1
(
Fig. S5). The G bond centred at 1580 cm is attributed to the
2
in-plane bond stretch of sp -bonded carbon atoms in 2D
-1
hexagonal lattice. The D bond located at 1360 cm is assigned
4
to the vibration of carbon atoms of disordered graphite. The
relative intensity of D and G bond (I /I ) is an indicator of the
1
D
G
disorder degree in a graphite structure. The I /I ratio of
D
G
HPNSC calculated was 3.7, indicating that nitrogen and sulfur
co-doping led to high-density defects in the carbon
1
5
framework.
The selective oxidation of silanes to silanols or silyl ethers
has been studied extensively using noble or transition metals
9
catalysts. In this work, we attempted to use the as-prepared
HPNSC to replace the metal-based catalysts for the oxidative
coupling of silanes with alcohols, and dimethylphenylsilane (1a)
was used as a model substrate. The results at different
conditions are given in Table 1. The conversion was very low
without the catalyst (<1%, Table 1, entry 1). To our delight, the
Fig. 1 a-b) SEM images and c) TEM image of the HPNSC; d) HPNSC could promote the reaction effectively. The selectivity
nitrogen adsorption/desorption isotherm and e) BJH pore size to the desired silyl ether (1b) increased with temperature up
distribution curve; f) HADDF-STEM image and the to 120 °C, and reached 99.6% at full conversion (Table 2 entry
corresponding EDX elemental mapping images of nitrogen 8). The 1b selectivity was lower at shorter reaction time.
2
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Although the surface area of the NSPC-SBA was similar to that of N and S heteroatoms and the hierarchical structure are
of the HPNSC, the former gave much lower conversion at the
Table 1. Oxidative coupling of dimethylphenylsilane(1a) with n-
crucial for the excellent catalytic performance of the HPNSC.
The catalytic performance of HPNSC was also examined in
the oxidative coupling of other silanes with alcohols. As shown
in Table 2, good to medium selectivity of silyl ethers were
achieved with excellent conversion. Aromatic silanes were
oxidized effectively in the presence of alcohols. Both dimethyl-
phenylsilane and diphenylsilane in butanol gave excellent yield
of the corresponding ethers (99.6% and 98.4%). Owing to low
boiling point of ethanol and methanol, long time was required
to obtain the desired yield of silyl ethers. The selectivity of
silanes generally decreases with the number of Si-H bonds.
Oxidation of phenylsilane afforded trialkoxyphenylsilane in
medium yield (Table 2, entry 7-9) due to the competitive
a
butanol over the HPNSC at different conditions.
b
Entry
T(°C)
t(h)
Conv.
Sel. (%)
b
(%)
1b
1c
-
c
1
120
90
16
16
16
16
16
16
8
<1
99.9
73.3
78.2
83.6
99.6
98.9
83.6
92.4
99.9
99.9
94.7
2
3
4
5
6
7
100
100
100
100
100
100
100
23.9
21.8
96.5
15.9
11.0
2.2
0.4
0.6
10.0
3.2
-
100
110
120
130
120
120
120
120
120
1
6
formation of disiloxane or siloxane oligomers. It is worth
noting that sterically hindered triphenylsilane was converted
into the target silyl ethers with good yield (Table 2, entry 10-
1
2). However, Au nanoparticles supported on nanohydroxy-
apatite gave only 25% yield of methoxytriphenylsilane in the
9k
oxidative couple of triphenylsilane with methanol. Moreover,
8
12
16
16
16
Table 2. Results of the oxidative coupling of silanes with
a
alcohols catalysed by HPNSC
d
1
0
e
1
1
-
f
1
2
5.3
a
Reaction conditions: silane (1 mmol), alcohol (3 ml), HPNSC
b
(
20 mg), 120
°
obtained from GC with dodecane as internal standard. No
C/16 h. The conversion and the selectivity were Ent.
R
1
R
2
R
3
R
4
T
t
Conv.
Sel.
c
b
b
d
e
f
(°C) (h)
(%)
(%)
catalyst was used. NSPC-SBA (20 mg). CNTs (20 mg). HPNC
20 mg)
(
1
2
3
4
5
6
7
8
9
Ph Me Me n-Bu
120
90
16
24
48
16
48
48
48
48
48
24
48
48
16
24
48
100
100
100
100
100
100
100
100
100
98.0
85.4
99.1
100
100
100
99.6
94.4
80.1
98.4
85.1
99.9
82.8
63.1
69.2
99.9
99.9
99.9
82.4
99.9
99.9
same reaction condition than the latter probably due to lower
pore volume (Table 2 entry 10). Thus, it can be deduced that
the hierarchical structure of the HPNSC is beneficial to improve
catalytic performance. However, conversion of dimethyl-
phenylsilane over CNT (carbon nanotube) was only 21.8%
Ph Me Me
Ph Me Me
Et
Me
n-Bu
Et
70
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Et
Ph
Ph
Ph
H
H
H
120
90
(
Table 1, entry 11). The activity of HPNC was also lower than
that of HPNSC (Table 1, entry 12). These results indicate that
the N and S heteroatom are all important for this reaction
.
H
Me
n-Bu
Et
70
It has been reported that graphitic nitrogen changed the
electronic structure of the adjacent carbon atoms and
promoted the carbocatalysis in the oxidation of arylalkanes
and alcohols. It is generally accepted that activations of the Si-
H bond in the silanes and O-H bond in the alcohol play a crucial
H
120
90
H
H
H
H
Me
n-Bu
Et
70
9
k-9o
role in the reaction.
We believe that the strong interaction
1
0
1
Ph
Ph
Ph
Et
Et
Et
Ph
Ph
Ph
Et
Et
Et
120
90
between the lone electron pairs in the various species N and S
with the Si-H bond and O-H bond also plays important role in
promoting the reaction. To investigate the heteroatom-doping
effect on the catalytic performance of the catalyst, the density
functional theory study was conducted using the Vienna ab
1
12
Me
n-Bu
Et
70
5
1
1
1
3
4
5
120
90
initio simulation package. The four types of graphene
structures and calculated adsorption energies (ΔEads) are
shown in Fig. S6. The computational details are described in
the Supporting Information. Compared with the pure, N-doped
or S-doped graphenes, the N and S co-doped graphene
exhibits the lowest adsorption energy. Thus, both co-existence
Et
Et
Me
70
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a
Zhang, J. Y. Yuan, T. P. Fellinger, M. Antonietti, H. R. Li and Y.
Wang, Angew. Chem. Int. Ed. 2013, 52, 6028.
Reaction conditions: silane (1 mmol), alcohol (3 ml), HPNSC
b
20 mg). The conversion and the selectivity were obtained
(
3
4
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Qin, X. Y. Shi, C. L. Sun, X. H. Bao, X. L. Feng and K. Mullen, J.
Am. Chem. Soc. 2017, 139, 4506; (b) A. Dhakshinamoorthy,
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M. A. Patel, F. X. Luo, M. R. Khoshi, E. Rabie, Q. Zhang, C. R.
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ACS Nano 2016, 10, 2305.
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from GC with dodecane as the internal standard.
aliphatic silane like triethylsilane also gave excellent yield of
the corresponding ethers (Table 2, entry 13-15).
The recyclability of the HPNSC was evaluated using the
reaction of dimethylphenylsilane with n-butanol. The catalyst
was readily recovered from the solution by centrifugation, and
the activity and selectivity were not changed notably after five
recycles (Fig. 3). The hierarchical structure and chemical
structure did not change obviously before and after the
recycling reaction (Fig. S7). These results indicate that the
HPNSC displayed excellent stability in the catalytic oxidation of
silanes.
5
6
7
1
36, 13554.
In summary, the HPNSC were very active and selective
metal-free catalyst for oxidative coupling of silanes with
alcohols. DFT calculation and control experiment showed that
both co-coping of N and S and the hierarchical structure were
crucial for the excellent catalytic performance. Moreover,
catalytic activity and selectivity of the HPNSC did not changed
notably after reused five times. We believe more reactions can
be conducted at metal-free condition using heteroatom-doped
hierarchically porous carbon materials as the catalysts.
This work was supported by the National Natural Science
Foundation of China (21603235, 21403248, 21174148), and
the Recruitment Program of Global Youth Experts of China,
and Chinese Academy of Sciences (QYZDY-SSW-SLH013).
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Table of Contents:
Hierarchically porous N and S co-doped carbon was used as efficient and robust metal-free
catalyst for oxidative coupling of silanes with alcohols.