Charge Modified Porous Organic Polymer Stabilized Ultrasmall Platinum Nanoparticles for the Catalytic Dehydrogenative Coupling of Silanes with Alcohols

Article abstract of DOI:10.1007/s10562-021-03763-w

Developing an ideal stabilizer to prevent the aggregation of nanoparticles is still a big challenge for the practical application of noble metal nanocatalysts. Herein, we develop a charge (NTf₂^?) modified porous organic polymer (POP-NTf₂) to stabilize ultrasmall platinum nanoparticles. The catalyst is characterized and applied in the catalytic dehydrogenative coupling of silanes with alcohols. The catalyst exhibits excellent catalytic performance with highly dispersed ultrasmall platinum nanoparticles (ca. 2.22?nm). Moreover, the catalyst can be reused at least five times without any performance significant loss and Pt NPs aggregation. Graphic Abstract: [Figure not available: see fulltext.]

Full text of DOI:10.1007/s10562-021-03763-w

Catalysis Letters
https://doi.org/10.1007/s10562-021-03763-w
Charge Modifed Porous Organic Polymer Stabilized Ultrasmall
Platinum Nanoparticles for the Catalytic Dehydrogenative Coupling
of Silanes with Alcohols
Shaohua Wu1 · Tongtong Su1 · Senqun Liu1 · Dan Cheng1 · Rong Zeng2 · Xiaohua Ma1 · Sanqi Liang1 ·
Shunmin Ding1 · Chao Chen1
Received: 11 April 2021 / Accepted: 1 August 2021
© The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021
Abstract
Developing an ideal stabilizer to prevent the aggregation of nanoparticles is still a big challenge for the practical application
−
of noble metal nanocatalysts. Herein, we develop a charge (NTf2 ) modifed porous organic polymer (POP-NTf2) to stabi-
lize ultrasmall platinum nanoparticles. The catalyst is characterized and applied in the catalytic dehydrogenative coupling
of silanes with alcohols. The catalyst exhibits excellent catalytic performance with highly dispersed ultrasmall platinum
nanoparticles (ca. 2.22 nm). Moreover, the catalyst can be reused at least fve times without any performance signifcant
loss and Pt NPs aggregation.
Graphic Abstract
Keywords Porous organic polymer · Dehydrogenative coupling · Charge modifed · Silanes · Noble metal nanocatalysts
1 Introduction
Shaohua Wu and Tongtong Su have contributed equally to this
work.
Silyl ethers are widely used as silylating agents and sur-
face modifcation reagents for many industrial applications
[1–5]. Silyl ethers are typically obtained from halosilanes
that react with alcohols, but, besides the generation of cor-
rosive hydrogen halides, the use of halosilanes has disadvan-
tages in terms of atom efciency with respect to the use of
silanes [6]. Thus, a greener route, catalytic dehydrogenative
coupling of silanes with alcohols to synthesize silyl ethers
* Rong Zeng
zengrongnc@163.com
* Shunmin Ding
dingshunmin2007@163.com
* Chao Chen
chaochen@ncu.edu.cn
Extended author information available on the last page of the article
Vol.:(0123456789)
1 3

S. Wu et al.
has been developed because the only by-product would be
hydrogen gas. Previously, noble metals (such as Rh, Ru, Ir
and Pd) complexes [6–10] were generally used as highly
efcient homogeneous catalysts for this reaction. Neverthe-
less, most such conventional homogeneous systems sufer
from poor recyclability, limiting their industrial application.
Therefore, the development of efcient heterogeneous cata-
lysts is highly desired.
Recently, many heterogeneous catalysts have been
developed for this reaction [11–19], including copper metal
organic framework (Cu–MOF) [11], nanoporous silver/pal-
ladium [12, 13] and supported noble metal nanoparticles
(NMNPs) [14–19]. The copper ions of Cu–MOF are eas-
ily leaching into the catalytic systems. The efective atom
utilization of nanoporous silver/palladium catalysts is too
low. For supported noble metal nanocatalyst, the small size
of NMNPs is the key factor to its excellent catalytic perfor-
mance because of the intrinsic electronic structure, large
fraction of surface atoms, and quantum size efect. Unfor-
tunately, the high surface energies of ultra small NMNPs
promote severe aggregation and particle growth, resulting
in the drastic loss of their catalytic activity [20]. Up to date,
one popular approach to enhance aggregation resistance
is to confne NMNPs inside a nanoporous support, where
the inherently narrow pore dimensions provide an external
physical barrier to mitigate the aggregation and growth rate
of the NM species. However, the inherently narrow pore
dimensions limit the common usage of these catalysts due
to some large reactants can’t easily access to the active cent-
ers [21–24].
Scheme 1 The synthetic route to POP-NTf2@Pt
the crystallite size of Pt NPs on POP-I enlarges from 2.7 to
5.2 nm with a signifcant loss of catalytic activity from 75
to 52%.
2 Experimental Section
2.1 Materials
4-Vinylpyridine (95%) and divinylbenzene (80%) were pur-
chased by Aladdin Industrial Inc. Azobisisobutyronitrile
(AIBN, 99%), iodoethane and bistrifuoromethanesulfon-
imide lithium salt (LiNTf2) were purchased by Adamas
Reagent Co., Ltd and other reagents were from Sinopharm
Chemical Reagent Co., Ltd. All of the reagents and solvents
used in this study were AR grade and utilized without fur-
ther purifcation.
Porous organic polymers constitute a very promising
class of advanced porous materials and have attracted great
attention in the feld of catalysis due to their organic scaf-
folds can be easily synthetically tuned and functionalized
[25–28]. In our previous work [29], the charge modulation
approach was reported in engineering nanoporous organic
frameworks to stabilize Au NCs. The key to our success
lies in the installation of abundant regulated charge species
(F−) within the framework, inducing strong surface interac-
tions against Au NCs aggregation. As literature reported,
the halide ions as charged stabilizer is not suitable for stabi-
lizing many noble metal NPs, which can cause the poison-
ing of the active sites [30, 31]. Thus, the halide ions-free
charged stabilizer should be developed. In this study, we
use NTf2− exchanged I− on the porous organic polymer to
stabilize Pt NPs (POP-NTf2@Pt, Scheme 1) for catalytic
dehydrogenative coupling of silanes with alcohols. The as-
prepared catalyst (POP-NTf2@Pt) shows homogeneously
dispersed Pt NPs on POP- NTf2 with the particle size of ca.
2.22 nm, crystallite size of 2.1 nm and exhibits high activ-
ity and reusability in the reaction. As expect, after reuse
fve times, the crystallite size of Pt NPs on POP-NTf2 keeps
at ca. 2.1 nm, and remains high performance. In contrary,
2.2 Catalyst Preparation
2.2.1 Synthesis of POP
The POP was synthesized according the reported method
[32]. The detail procedure was given in supporting
information.
2.2.2 Synthesis of POP‑I
1186 uL of iodoethane (14.8 mmol) was added into 300 mL
of acetonitrile and then, 1.00 g of POP was induced. The
resulting mixture was refuxed for 24 h in oil bath (80 °C).
Finally, fltered and washed by acetonitrile and ethanol for
fve times and dried under vacuum at 80 °C for 12 h. The
obtained sample was denoted as POP-I.
1 3

Charge Modifed Porous Organic Polymer Stabilized Ultrasmall Platinum Nanoparticles for…
2.2.3 Synthesis of POP‑NTf2
were then charged to round bottom fask together with the
recovered catalyst to carry out the next run reaction.
NTf2− was used to exchange I− on POP-I. The typical pro-
cedure is as follows: 0.25 g of LiNTf2 and 0.1 g POP-I were
added into 100 mL deionized water, and stirred vigorously
at room temperature for 24 h. Subsequently, the mixture
was washed and fltered with deionized water. The same
exchanging procedure was repeated for 3~4 times. Finally,
fltered and washed with deionized water and dried under
vacuum overnight at 80 °C. The sample was denoted as
POP-NTf2.
3 Results and Discussion
The pristine POP and POP-I were prepared according to the
previous literature [32, 33] and the POP-NTf2 was prepared
by the ions exchange method. The SEM (Fig. S1), TG analy-
sis (Fig. S2) and FT-IR results confrmed that POP was suc-
−
cessfully prepared. To prove charge species (I− and NTf2 )
were successfully modifed on POP, FT-IR spectra of POP,
POP-I, POP-NTf2 and POP-NTf2@Pt were performed. As
shown in Fig. S3, The POP displays typical bond absorptions
at 1642 cm−1 and 1229 cm−1(C=N) and 1600 cm−1 (C=C)
[32]. Compared to the spectra of the POP, a new peak at
1167 cm−1 ascribed to the C–N+ bond vibration was clearly
observed in the spectra of POP-I [33]. The POP-NTf2 and
POP-NTf2@Pt displayed four new peaks at 1191, 1141 cm−1
and 1349, 1059 cm−1, which ascribed to S=O bond and C–F
2.2.4 Synthesis of POP‑NTf2@Pt
H2PtCl6·6H2O (1 mL, 2 mg Pt mL−1, 0.0039 mmol) was
dropped into 0.1 g POP-NTf2 in 50 mL deionized water.
Then, the resulting mixture was stirred for 2 h, and then
1 mL NaBH4 (0.2 mmol mL−1) was continued to be dropped
and stirred at room temperature for 3 h. Finally, fltered and
washed by water and ethanol, and then dried under vacuum
at 80 °C for 12 h. The resulting catalyst was denoted as
POP-NTf2@Pt. for comparison, POP@Pt and POP-I@Pt
were prepared by the same method using POP and POP-I as
carriers, respectively.
−
bond from NTf2 , respectively [34]. This proves that the
POP, POP-I and POP-NTf2 are successfully prepared.
The powder XRD was performed to evaluate the struc-
tural features of the as-prepared samples. As shown in
Fig. 1, the peak at 2θ = 20° in all the samples is ascribed
to the amorphous porous organic polymer structure. After
stabilizing Pt NPs, a new peak at about 39.6° and 46.0° is
appeared in POP-I@Pt and POP-NTf2@Pt, corresponding
to the Pt (111) and Pt (200) crystal faces [35]. The Pt crys-
tallite size of POP-I@Pt and POP-NTf2@Pt calculated by
the Debye–Scherrer equation is 2.7 nm and 2.1 nm based
on Pt (111), respectively. Moreover, for comparison, Pt
supported on POP without charged stabilizer was prepared
2.3 Characterization
FT-IR spectra were recorded on a Nicolet 5700 instru-
ment. X-ray difraction (XRD) profles were collected on a
XD-3 difractometer with Cu Kα radiation (λ=0.15418 nm,
40 kV/30 mA) at the scanning step of 4°min−1. Thermo-
gravimetric analyses (TGA) were performed on a SDT
Q600 thermal gravimetric analyzer under N2 atmosphere
with a heating rate of 10 °C min−1 from room temperature
to 800 °C. N2 absorption–desorption curves were carried out
on a Quantachrome Autosorb iQ2 physisorption analyzer.
Transmission Electron Microscope (TEM) was measured on
a JEM-2100 instrument.
2.4 Catalyst Tests
The catalytic dehydrogenative coupling of silanes with alco-
hols was carried out in a 50 mL fask equipped with a refux
condenser and a magnetic stirrer. 1 mol of silanes, 3 mL
of alcohols and catalyst was added and stirred at a given
temperature for a specifc time under air atmosphere. The
products were determined by GC–MS and analyzed by GC
using dodecane as internal standard with a FID detector.
The reaction cycles were carried out using POP-NTf2@
Pt and POP-I@Pt catalysts in the reaction of dimethylphe-
nylsilane with ethanol at 70 °C for 10 h. After each cycle
the catalyst was separated, washed with ethanol and dried
under vacuum at 80 °C for 12 h. Fresh reactants and solvent
Fig. 1 XRD patterns of the as-prepared samples
1 3

S. Wu et al.
by the similar method. The XRD peaks of Pt (111) and Pt
(200) crystal faces is sharper than that of POP-I@Pt and
POP-NTf2@Pt and the crystallite size of Pd NPs is large to
4.0 nm. The results indicate that charged stabilizer is very
important for controlling the crystallite size of Pt NPs and
NTf2− modifed POP can replace halide ions (I−) modifed
POP as charged stabilizer to stabilize Pt NPs.
of (2.22 0.19) nm are homogeneously stabilized on the
charge modifed porous organic polymer (POP-NTf2). This
result is in good agreement with the XRD result.
To explore the catalytic performance of the as prepared
catalysts, the dehydrogenative coupling of dimethylphe-
nylsilane with ethanol was selected as the model reaction.
As shown in Table 1, no desired silyl ether (dimethyl-phe-
nyl-ethoxysilane, 1b) is formed by using pristine POP as
a catalyst or without any catalyst (Table 1, entries 1–2).
Like the Lewis acid catalyst nitrenium salts, POP-I (POP-
NTf2) shows 15% (35%) dimethylphenylsilane conversion,
78% (80%) selectivity of 1b and 22% (20%) selectivity of
disiloxane byproduct 1c (Table 1, entries 3–4) at 70 °C for
24 h. However, we were excited to fnd that the desired 1b
was furnished (>99% selectivity) with no formation of the
disiloxane byproduct 1c and the yield of 1b is 61%, 76%
and>99% (Table 1, entries 5–7 and Fig. S4) for POP@Pt,
POP-I@Pt and POP-NTf2@Pt at 70 °C for 24 h, respectively.
Finally, the reaction conditions were optimized by varying
the parameters afecting the reaction, such as the tempera-
ture (Table 1, entries 7–11), catalyst amount (Table 1, entries
7, 12–13) and time (Table 1, entries 7, 14–15 and Fig. S4)
using POP-NTf2@Pt. Specimens were drawn periodically to
monitor the degree of reaction by determining the conver-
sion and selectivity using GC with FID detector. The conver-
sion is rather low (66%) with only 57% selectivity towards
the desired product at 50 °C for 24 h. With the tempera-
ture increase, the conversion improves to 99% with>99%
selectivity of 1b at 70 °C for 24 h, and then the conversion
remains constant, but the selectivity decreases slightly from
70 to 90 °C. The efect of catalyst amount is carried out
at 70 °C for 24 h, the result reveals the catalyst requires at
Figure 2 shows the N2 adsorption and desorption iso-
therms of the as-prepared POP, POP-I, POP-NTf2 and
POP-NTf2@Pt. The N2 adsorption and desorption iso-
therms (Fig. 2a) and pore size distributions (Fig. 2b) dem-
onstrates that all samples display type-IV curves and pre-
sent mesoporous structure, respectively. The mesoporous
structure is believed to provide a pathway for the fast dif-
fusion of reactants into the inner pores and to the active
sites. The BET surface area of the pristine POP and charge
modifed POP samples (Table S1) follows the order POP
(486 m2 g−1)>POP-I (130 m2 g−1)>POP-NTf2 (86 m2 g−1).
This because the POP is functionalized by CH3CH2I
to POP-I, and then the small one (I−) is replaced by the
−
larger size charge species NTf2 to block more nanopo-
res. More evidence can be found in the pore volume of
POP (0.61 cm3 g−1), POP-I (0.44 cm3 g−1) and POP-NTf2
(0.23 cm3 g−1). After 1.7 wt.% Pt is stabilized on POP-
NTf2, the BET surface and pore volume of POP-NTf2@Pt
(79 m2 g−1 and 0.24 cm3 g−1) shows no signifcant loss com-
paring to POP-NTf2, which may illustrate that the stabilizing
Pt NPs is very small and can’t block the inner pores.
To further understand the morphology of POP-NTf2@
Pt, TEM (Fig. 3) images were collected. As expected, the
mesoporous structure can be clearly observed (Fig. 3a).
Moreover, Fig. 3c shows that the small Pt NPs with the size
Fig. 2 The N2 adsorption and desorption isotherms (a) and pore size distributions (b) of the as-prepared POP, POP-I, POP-NTf2 and POP-
NTf2@Pt
1 3

Charge Modifed Porous Organic Polymer Stabilized Ultrasmall Platinum Nanoparticles for…
Fig. 3 TEM images (a–d) and Pt NPs size distribution (c) of POP-NTf2@Pt
least of 10 mg. The degree of the conversion of dimethyl-
phenylsilane to 1b at 70 °C as a function of the reaction time
is shown in Fig. S4. The results indicate that the complete
conversion of dimethylphenylsilane to the 1b requires 10 h.
Stability and reusability are crucial aspects for the appli-
cation of heterogeneous catalysts in liquid catalytic sys-
tems. The TG analysis results (Fig. S2) indicate that POP,
POP-NTf2 and POP-NTf2@Pt are stable below 300 °C. And
POP-NTf2@Pt can be reused at least fve times without any
signifcant decrease in the catalytic activity (Fig. 4a), the
Pt content of the reused catalyst is kept at about 1.7 wt.%
(Table S1) and the Pt content of the fltered solution could
not be detected by the ICP-OES instrument. Moreover,
the intensity of XRD peaks of Pt (111) and TEM images
(Fig. S5) shows no signifcant change between the fresh
and the used catalyst (Fig. 4b). However, the Pt (111) peak
of POP-I@Pt get sharper and the crystallite size of Pt NPs
enlarges from 2.7 nm to 5.2 nm (Fig. S6a) after reused fve
times with a signifcant loss of catalytic activity from 75 to
52% (Fig. S6b). The reason likes the literature reported [30],
halide ions (X−) as charged stabilizer can facilitate noble
metal (M+) to form Mσ+–Xσ−–Mσ+ bond, and then the M-M
bond formatted, the M NPs fnally aggregated. These results
indicate that NTf2− is a more suitable charged stabilizer than
I− for the dehydrogenative coupling of silanes with alcohols
to prevent Pt NPs aggregation.
In view of the importance of silyl ether moieties, a range
scope of silane and alcohol substrates was examined by using
the POP-NTf2@Pt catalyst. As depicted in Table 2, a broad
range of diverse alcohols and silanes could participate in the
1 3

S. Wu et al.
Table 1 Dehydrogenative coupling of dimethylphenylsilane (1a) with ethanol over the catalysts under diferent conditions a
Entry
Catalyst
W (mg)
T (℃)
t (h)
Conv. (%)
1a
Sel. (%)
1b
Yield (%)
1c
1b
1c
1
2
3
4
5
6
7
8
None
POP
POP-I
POP-NTf2
POP@Pt
POP-I@Pt
POP-NTf2@Pt
POP-NTf2@Pt
POP-NTf2@Pt
POP-NTf2@Pt
POP-NTf2@Pt
POP-NTf2@Pt
POP-NTf2@Pt
POP-NTf2@Pt
POP-NTf2@Pt
10
10
10
10
10
10
10
10
10
10
10
5
70
70
70
70
70
70
70
50
60
80
90
70
70
70
70
24
24
24
24
24
24
24
24
24
24
24
24
24
10
8
0
0
15
35
61
76
>99
66
99
>99
>99
85
>99
>99
78
–
–
78
80
>99
>99
>99
57
64
>99
90
–
–
22
20
0
0
0
43
36
0
10
30
0
–
–
12
28
61
76
>99
38
64
>99
90
60
>99
>99
78
–
–
3
7
0
0
0
28
36
0
10
25
0
9
10
11
12
13
14
15
70
20
10
10
>99
>99
>99
0
0
0
0
aReaction conditions: 1a (1 mmol), ethanol (3 mL) and the conversion and the selectivity were obtained from GC by using n-dodecane as the
internal standard
Fig. 4 The reusability of POP-NTf2@Pt in dehydrogenative coupling of dimethylphenylsilane with ethanol (a) and the XRD patterns of POP-
NTf2@Pt fresh and after reused fve times (b)
1 3

Charge Modifed Porous Organic Polymer Stabilized Ultrasmall Platinum Nanoparticles for…
Table 2 The dehydrogenative coupling of various silanes with diferent alcohols over POP-NTf
a
2@Pt
Entry
R4−nSiHn
R’OH
R4−nSi(ORʹ)n
T (°C)
R4−nSiHn
Conv. (%)
R4−nSi(ORʹ)n Sel. R4−nSi(OR’)n
TONb
(%)
Yield (%)
1
2
3
4
5
6
7
8
9
Ph(Me)2SiH
MeOH
EtOH
n-BuOH
MeOH
EtOH
n-BuOH
MeOH
EtOH
Ph(Me)2SiOMe
Ph(Me)2SiOEt
Ph(Me)2SiOBu
Ph2Si(OMe)2
Ph2Si(OEt)2
Ph2Si(OBu) 2
PhSi(OMe)3
PhSi(OEt)3
65
70
100
65
70
100
65
88
81
>99
75
82
>99
97
95
91
>99
71
>99
75
65
>99
93
90
83
86
814
1147
860
>99
>99
79
>99
96
95
91
Ph2SiH2
PhSiH3
746
1147
1067
1032
952
70
100
n-BuOH
PhSi(OBu)3
86
986
aReaction conditions: silane (1 mmol), alcohol (3 mL), Pt/MOP-NTF2 (10 mg) and 10 h. The conversion and the selectivity were obtained from
GC by using dodecane as the internal standard
bTON=molar of product/molar of catalyst
2. Anbu N, Dhakshinamoorthy A (2017) J Colloid Interface Sci
490:430
reaction efciently in excellent silanes conversions (79~99%),
desired silyl ethers yields (65~99%) and turnover numbers
(746~1147).
3. Cardoso JMS, Lopes R, Royo B (2015) J Organomet Chem
775:173
4. Belelli PG, Ferreira ML, Damiani DE (2000) J Mol Catal A Chem
159:315
4 Conclusions
5. Blackwell JM, Foster KL, Beck VH, Piers WE (1999) J Org Chem
64:4887
In conclusion, NTf2− modifed porous organic polymer as a
charged stabilizer can efectively suppress the aggregation of
the ultrasmall Pt NPs species. The resulting heterogeneous
POP-NTf2@Pt catalyst exhibits excellent performance in the
dehydrogenative coupling of silanes with alcohols, suggesting
great promise for catalytic applications. This charged stabi-
lizer not only can replace the halide ions -stabilizers which
can make catalyst poisoning, but also simultaneously opens up
new possibilities for the development of novel metal nanopar-
ticles catalysts displaying long-term stability and high activity.
6. Krueger A, Albrecht M (2012) Chem Eur J 18:652
7. Gonzalez-Fernandez R, Crochet P, Cadierno V (2020) Dalton
Trans 49:210
8. Ventura-Espinosa D, Carretero-Cerdan A, Baya M, Garcia H,
Mata JA (2017) Chem Eur J 23:10815
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Organometallics 22:2387
10. Lv H, Laishram RD, Chen J, Khan R, Zhu Y, Wu S, Zhang J, Liu
X, Fan B (2021) Photocatalyzed cross-dehydrogenative coupling
of silanes with alcohols and water. Chem Commun. https://doi.
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12. Li Z, Zhang C, Tian J, Zhang Z, Zhang X, Ding Y (2014) Catal
Commun 53:53
Supplementary Information The online version contains supplemen-
tary material available at https://doi.org/10.1007/s10562-021-03763-w.
13. Li Z, Lin S, Ji L, Zhang Z, Zhang X, Ding Y (2014) Catal Sci
Technol 4:1734
Acknowledgements This research was supported by the National Natu-
14. Kronawitt J, Dulle M, Schmalz H, Agarwal S, Greiner A (2020)
ACS Appl Nano Mater 3:2766
ral Science Foundation of China (Grant No. 22002056).
15. Schoebel J, Burgard M, Hils C, Dersch R, Dulle M, Volk K, Karg
M, Greiner A, Schmalz H (2017) Angew Chem Int Ed 56:405
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ACS Catal 7:1720
Declarations
Conflict of interest There are no conficts to declare.
17. Dhiman M, Chalke B, Polshettiwar V (2017) J Mater Chem A
5:1935
18. Dhakshinamoorthy A, EsteveAdell I, Primo A, Garcia H (2017)
ACS Sustain Chem Eng 5:2400
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Authors and Afliations
Shaohua Wu1 · Tongtong Su1 · Senqun Liu1 · Dan Cheng1 · Rong Zeng2 · Xiaohua Ma1 · Sanqi Liang1 ·
Shunmin Ding1 · Chao Chen1
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
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