Eight-membered ring petal-shaped V8 cluster: An efficient heterogeneous catalyst for selective sulfur oxidation

Article abstract of DOI:10.1016/j.ica.2020.120198

An eight-membered ring petal-shaped cluster [V₈^ⅣO₈(CH₃O)₁₆(C₂O₄)](C₆NH₁₆)₂(CH₃OH)₂ (V₈) has been successfully designed and synthesized via hydrothermal method. Structure analysis revealed that each vanadium atom was in an octahedral geometrical configuration six-coordinated, two adjacent vanadium atoms were linked by oxygen atoms on oxalic acid to form a ring. The selective sulfur oxidation experiments reveal that V₈ had good catalytic activity under mild conditions, and the removal rate of phenyl sulfide was >99% within 4 h at 40 °C. In addition, the open aperture Z-scan test of V₈ was carried out and found that V₈ also has latent application value as nonlinear optical (NLO) material.

Full text of DOI:10.1016/j.ica.2020.120198

Inorganica Chimica Acta 517 (2020) 120198
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Inorganica Chimica Acta
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Research paper
Eight-membered ring petal-shaped V cluster: An efficient heterogeneous
8
catalyst for selective sulfur oxidation
a
a
a
a
a
a
Qing-Dong Ping , Jia-Peng Cao , Ye-Min Han , Mu-Xiu Yang , Ya-Lin Hong , Jia-Nian Li ,
a
a
a,
*
a,b,*
Ji-Lei Wang , Jia-Li Chen , Hua Mei , Yan Xu
a
College of Chemical Engineering, State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing 210009, PR China
State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, PR China
b
A R T I C L E I N F O
A B S T R A C T
An eight-membered ring petal-shaped cluster [V 8Ⅳ O (CH O) (C O )](C NH ) (CH OH) (V ) has been suc-
Keywords:
8
3
16
2
4
6
16
2
3
2
8
Polyoxovanadates
Selective sulfur oxidation
NLO materials
cessfully designed and synthesized via hydrothermal method. Structure analysis revealed that each vanadium
atom was in an octahedral geometrical configuration six-coordinated, two adjacent vanadium atoms were linked
by oxygen atoms on oxalic acid to form a ring. The selective sulfur oxidation experiments reveal that V
8
had good
◦
catalytic activity under mild conditions, and the removal rate of phenyl sulfide was >99% within 4 h at 40 C. In
8 8
addition, the open aperture Z-scan test of V was carried out and found that V also has latent application value
as nonlinear optical (NLO) material.
1
. Introduction
chemistry are proposed, the research of catalysis further reach a climax.
POMs as molecular catalysts are widely used in the selective sulfur
oxidation of organic sulfides in fuels. POMs have contributed to the
development of green and sustainable catalysts because of its unique
properties and novel structures. Polyoxovanadates (POVs) as a unique
branch of POMs have attracted an increasing number of attention due to
not only variable configuration but also preferable catalytic activity
without noble metal [15–20]. Up to now, a large number of POVs have
been reported. Many studies on vanadium-based POMs synthesis and its
With modern development of the automobile industry, reducing the
sulphur content of fuel oil has become an attractive area of science in
recent years [1,2]. Sulfides are burned in the air to form sulfur oxides
(
SO
x
), which may lead to acid rain [3–5]. This is an issue that must be
addressed by the current environmental development. Therefore, it is
important to remove the sulfur from original raw materials in an envi-
ronmentally friendly way. Selective sulfur oxidation and Catalytic
hydrodesulfurization (HDS) are two of the most commonly used desul-
furization methods [6]. Compared with traditional HDS, selective sulfur
oxidation has become a research hotspot due to its mild reaction con-
ditions, high desulfurization rate, low equipment investment, and low
cost [7]. Various catalysts have been tested for selective sulfur oxidation
process, such as ionic liquid [8], mesoporous silica [9], transition metal
complex [10], tungsten supported on resin [11] and polyoxometalate
compounds [12]. Among them, due to the method of synthesizing pol-
yoxometalates (POMs) is simple and the strong adjustability of its
structure, it has been widely studied [13]. At the same time, sulfur-
containing compounds can be oxidized using heteropolyacids as the
heterogeneous catalyst under mild conditions to form corresponding
sulfoxides and sulfone, which can be easily removed by solvent extrac-
tion or adsorption [4,14].
structure have been reported [21–24], for example, the octanuclear
III
vanadium (III) wheel-like cluster [(CH
3
)
2
NH
2
]
17.4[V
8
(
μ
2
-OH)
(μ -
8 2
SO
4 4
)16][SO ]0.7. Although the charming structures, the research on their
selective sulfur oxidation properties are relatively insufficient. Based on
Ⅳ
Ⅴ
2 2 8 4 3 4 4 4 3
our group previous study in [(C N H ) (CH O) V V O16] CH OH,
obtaining excellent catalytic conversion for the oxidation of sulfides
which indicates that it has latent application value as heterogeneous
catalysts [25]. Therefore, we have done further investigation synthesis
and selective sulfur oxidation reactions of vanadium compounds.
Based on the above considerations, an eight-membered ring petal-
shaped cluster [VⅣ
O (CH O)16(C O )](C NH16) (CH OH) (V ) has
8 8 3 2 4 6 2 3 2 8
been successfully synthesized. Single Crystal X-ray diffraction (SCXRD)
showed that each vanadium atom was six-coordinated, and the two
adjacent vanadium atoms were linked by oxygen on methanol, and were
further linked by oxygen from oxalic acid to form an eight-membered
In recent years, as the concept of green chemistry and molecular
*
Corresponding authors.
E-mail addresses: meihua@njtech.edu.cn (H. Mei), yanxu@njtech.edu.cn (Y. Xu).
https://doi.org/10.1016/j.ica.2020.120198
Received 15 August 2020; Received in revised form 1 December 2020; Accepted 10 December 2020
Available online 16 December 2020
0
020-1693/© 2020 Elsevier B.V. All rights reserved.

Q.-D. Ping et al.
Inorganica Chimica Acta 517 (2020) 120198
Table 1
8
Crystallographic data for compound V .
Empirical formula
32 88 2 30 8
C H N O V
ꢀ
1
Formula weight (g⋅mol
Temperature (K)
Crystal system
Space group
a (Å)
)
1388.56
296(2)
Triclinic
P-1
8.6561(13)
13.398(2)
13.975(2)
96.536(2)
106.722(2)
100.826(2)
1500.1(4)
1
b (Å)
c (Å)
◦
α
( )
◦
β ( )
◦
γ ( )
3
)
V (Å
Z
ꢀ
3)
D
c
(mg cm
1.537
ꢀ
1
Absorption coefficient (mm
)
1.269
F (000)
718
◦
θ ( )
1.546 to 25.498
Limiting indices
ꢀ 10 ≤ h ≤ 10,
ꢀ
16 ≤ k ≤ 6,
16 ≤ l ≤ 16
ꢀ
Reflections collected
11,327
8
Fig. 1. View of the structure of V .
Independent reflections
Data/restraints/parameter
5524
5524/31/336
0.0332
R
int
X-ray diffraction (SCXRD) analysis data was collected on a Bruker Apex
II CCD equipped (296 K) with a sealed tube X-ray source (Mo-K radi-
2
Goodness of fit on F
1.063
α
a,
b
R
R
1
wR
, wR
2
(I > 2
σ
(I))
0.0452, 0.1277
0.0616, 0.1365
ation, λ = 0.71073 Å) operating at 45 kV and 30 mA. Direct solution and
full matrix least squares refinement of the structure are carried out by
SHELXL-2018/3 and Olex2 package.
1
2
(all data)
a
b
2
o
2 2
c
2 2 1/2
R
1
= Σ||F
o
| - |F
c
||/Σ|F
o
|. wR
2
= Σ[w(F
- F
) ]/Σ[w(F
o
) ]
.
ring petal-shaped V
8
Cluster. The catalytic activity of V
8
as heteroge-
3
. Results and discussion
neous catalyst in the oxidation of various sulfides with tert-butyl hy-
droperoxide as an oxidant was further investigated, showing high
catalytic activity and selectivity to linear sulfides. Besides, the third-
order nonlinear optics property was researched and the two-photon
3
.1. Synthesis
Due to its operability and strong tunability, solvothermal synthesis
absorption cross-sections (
σ
8
) value of V indicates that it has the po-
[
26–29] has been widely used in crystal growth in recent years.
tential to be applied in NLO field.
Appropriate reaction conditions are the key to crystal growth, such as
reaction temperature, time, the amount of solvent and the type of
counter cation [30]. In this work, an eight-membered ring petal-shaped
2
. Experimental
.1. Materials and instruments
All chemicals are analytically pure and used without any purifica-
8
V cluster was successfully synthesized. Interestingly, the compound can
2
be successfully synthesized using L-tartaric acid or D-tartaric acid, while
with the addition of D-tartaric acid can get good crystal quality with high
yield and have good repeatability. In the synthesis of V , tartaric acid
8
tion. A Nicolet Impact 410 was used to measure Fourier transform
infrared spectra at 273 K. At room temperature, using a Bruker D8X
was decomposed into oxalic acid, which played a role of stable the
structure. At the same time, we also tried other counter cations such as
trimethylamine, triethanolamine, tetrabutyl-ammonium hydroxide and
tetramethyl-ammonium hydroxide, but could not get the target product.
diffractometer using Cu-K
α radiation (λ = 0.154178 nm) with a scanning
◦
rate of 10 /min, X-ray diffraction (XRD) patterns were recorded in the
◦
range 5–50 . In a flowing N
2
atmosphere, TG was measured by a dia-
◦
◦
ꢀ 1
mond thermogravimetric analyzer (25 to 800 C, 10 C min ). The light
source we used in the NLO test is Chameleon II Femtosecond Ti: Sap-
phire Laser (140 fs, 80 MHz, 680–1080 nm).
3
.2. Structure description of compound
8
The single X-ray diffraction (SCXRD) reveals that V crystallized in
the Triclinic P-1 space group. As we can see from Fig. 1, the basic
Ⅳ
2
.2. Synthesis of [V
8
O
8
(CH
3
O)16(C
2
O
4
)] (C
6
NH16
)
2
(CH
3
OH)
2
(V
8
)
building block of the compound consists of an eight-membered ring
Ⅳ
8
2-
[
V
O
8
(CH
3 2 4
O)16(C O )] polyanion cluster, two free protonated trie-
At room temperature, ammonium metavanadate (0.15 g, 1.28 mmol)
thylamine and two free methanol molecules. In the main structure of the
and D-tartaric acid (0.05 g, 0.33 mmol) were dissolved in 10 mL meth-
anol solution, and then triethylamine (0.1 g, 0.99 mmol) was added.
After stirring for 2 h, the mixture was moved to a 25 mL reactor lined
Ⅳ
2-
8 8 3 2 4
[V O (CH O)16(C O )] polyanion cluster, two adjacent vanadium
atoms are linked by oxygen atoms which come from methanol, and then
are further linked by oxygen atoms from oxalic acid to form an eight-
◦
with Teflon and reacted at 120 C for three days. After being naturally
2-
4
membered ring petal-shaped V
8
Cluster (Fig. 1). Notably, C
2
O
groups
cooled to room temperature, the crystals in the shape of purple bars
in the center of the ring are decomposed from tartaric acid, which play a
(
Fig. S2) were observed after washing with methanol and dried. Yield:
6.55% (based on vanadium). Molecular formula:C32
Elemental analysis (EA, Calcd (Found), %):C, 27.47 (27.65); H, 6.67
6.34); N, 2.48 (2.02).
2-
2 4
role of stable the structure (50% occupied C O groups are disordered).
4
88 2 30 8.
H N O V
In compound, each vanadium atom is in an octahedral geometrical
configuration six-coordinated, connecting with six O atoms from four
methanol groups, one terminal oxygen and one oxalic acid group,
(
respectively (Fig. 3b). The structure of V is different from previous
2 4
reported for [(n-C N] [V (OCH 16(C O )] [24]. Although they
8
2
.3 Crystal structure determinations
The crystallographic data of V
4
H
9
)
4
2
8
O
8
3
)
have the same metal structure, while in this work, counter cation tet-
rabutyl ammonium is substituted by triethylamine. Interestingly, with
8
is given in the Table 1. Single crystal
2

Q.-D. Ping et al.
Inorganica Chimica Acta 517 (2020) 120198
Ⅳ
2-
8 8 3 2 4
Fig. 2. Basic structural models of (a) the [V O (CH O)16(C O )] , and (b) ball-and-stick models of the petal-shaped ring. (c) Polyhedral models of the compound.
Secondary building unit (SBU). The H atoms and carbon atoms are omitted for clarity.
Fig. 3. (a) A petal-shaped vanadium eight-membered ring. (b) The coordination mode for vanadium atoms in V8.
the addition of triethylamine not only as template, but also the pro-
tonated triethylamine molecules are used to balance the charge.
Meanwhile, for the purpose of better comprehending the structure,
compound is divided into two kinds of secondary building units (SBUs).
Two VO6 are connected by oxygen atoms from methanol molecules
facing into the ring to form SBU-1, while the other one forms SUB-2 in
the opposite direction of SBU-1, and then, two classes of SBU are
alternately arranged and tightly coupled by sharing vanadium atom to
and V4 = 4.120 for V
8
) have manifested that all V atoms are in the + 4
oxidation state (Table S2). Meanwhile, the magnetic properties of V
8
cluster was inspected and showed the existence of antiferromagnetic
coupling interactions for 8 ⅤⅣ ions (with S = 1/2, g = 2) (Fig. S6–7)
[34b], which further indicates that all vanadium atoms are in the + 4
oxidation state.
3
.3. Selective sulfur oxidation reaction
form a ring (Fig. 2). The V ꢀ O bond distances of V
8
is in the range of
1
7
.589–2.414 Å. The O ꢀ V ꢀ O angles of V
8
is in the range of
◦
The effect of POVs on the conversion of alkyl sulfide and benzene
6.45–100.14 . The V-O bond length and O-V-O bond angle in the
ring-containing substrates was evaluated to know the role of POVs as a
compound are consistent with the reported POVs [31–34a]. Bond
valence sum (BVS) calculations (V1 = 4.066, V2 = 4.116, V3 = 4.093
catalyst with dichloromethane as solvent, tert-butyl hydrogen peroxide
(
TBHP) as oxidant and dodecane as internal standard. The selective
3

Q.-D. Ping et al.
Inorganica Chimica Acta 517 (2020) 120198
Fig. 4. (a) Effects of reaction temperature, (b) O/S molar ratio, (c) different times on the removal of phenyl sulfide and (d) reactivity of V
8
in the cycled tests.
Reaction condition: O/S = 2 for (a) and T = 40 ◦C for (b).
sulfur oxidation tests were carried out in a three-mouth flask with
Table 2
magnetic agitator and reflux condensing tube at a temperature of 313 K.
a
Effect of the substrates on desulfurization.
Then 10 mg (7.2 × 10ꢀ 3 mmol) catalyst, 5 mL dichloromethane, a
b
ꢀ 1
)
Entry
1
Substrate
Conv (%)
29.7
Sele (%)
70.3
TOF (h
1.3
certain amount of TBHP and dodecane were added to the flask. After 4 h
reaction, the catalyst was separated from the solution by centrifugation,
and the desulfurization rate of sulfide was calculated by gas chroma-
tography (GC).
Under normal circumstances, reaction time, temperature and the
molar ratio TBHP/sulfur compounds are the main factors affecting se-
lective sulfur oxidation system. Therefore, the reaction temperature,
time and the molar ratio TBHP/sulfur compounds are firstly prelimi-
narily explored. To investigate the reaction temperature effect on sulfur
2
58.2
41.8
2.5
3
4
84.6
94.6
15.4
100
3.7
4.1
removal rate. Selective sulfur oxidation reactions were performed at 30,
◦
4
0, 50 and 60 C, and the results are shown in Fig. 4a. When the tem-
◦
perature was increased from 30 to 40 C, the conversion of phenyl sul-
fide was increased from 95.8% to 99%. Further increase of the
◦
5
100
67.8
4.3
4.3
temperature to 50 and 60 C the conversion rate remains unchanged.
The above analysis represents that increasing the reaction temperature
in a certain range is beneficial to the selective sulfur oxidation reaction
◦
of phenyl sulfide. Therefore, 40 C was chosen as the optimal temper-
6
7
100
100
100
ature for the subsequent reaction.
Furthermore, the amount of TBHP and reaction time were also
investigated. Therefore, the oxidation of different O/S molar ratio [n
81.0
4.3
c
c
9.8
56.5
–
(
TBHP)/n(phenyl sulfide)] was carried out using V
8
as the catalyst at
◦
4
0 C. As shown in Fig. 4b, when the O/S molar ratio reached to 2:1, the
8
a
100
100
4.3
sulfur removal rate increased to 99%, and the sulfur removal rate
remained unchanged within a certain range beyond this value. Subse-
quently, TBHP was then controlled at 2 mmol and the reaction time was
-3
Reaction conditions: substrates (1 mmol), catalyst (7.2 × 10 mmol), tert-
◦
b
varied. Fig. 4c shows the catalytic behavior of V
8
under different time
butyl hydrogen peroxide (2 mmol), methanol (5 mL), 40 C,4h. Selectivity to
◦
c
conditions, and it can be observed that as the increase of time at 40 C,
the removal of sulfide increased from 82.6% to 99%. From the
perspective of energy saving and reaction efficiency, 4 h and O/S = 2
were selected as the another best conditions for subsequent selective
sulfur oxidation process.
sulfoxides. The byproduct was sulfone. Without using catalyst.
To further study the catalytic capacity of V , the catalytic perfor-
8
mance on different substrates were researched under the optimal con-
ditions. Besides the representative phenyl sulfide, other sulfur
4

Q.-D. Ping et al.
Inorganica Chimica Acta 517 (2020) 120198
8 2 2 8
Fig. 5. (a) PXRD pattern of V immersed in CH Cl . (b) PXRD patterns for V before and after 5 recycle catalysis.
compounds such as alkyl sulfides, sulfides containing benzene ring and
other sulfide commonly found in fuels were also be researched. During
the selective sulfur oxidation on alkyl sulfides, the conversion rates of
diethyl sulfide and methylethyl sulfide all reached above 99%. And, the
8
removal of dibutyl sulfide was 84.6%. Table 2 shows that V catalyst can
remove not only some linear sulfides but also other benzene-containing
ring substrates. After the selective sulfur oxidation for 4 h, the desul-
furization percent varies in the sequence of methyl phenyl sulfide >
ethyl phenyl sulfide > dibenzothiophene > benzothiophene. Blank
contrast experiments show that in the absence of catalyst, the sulfides
can be oxidized to the corresponding sulfoxides, but the removal rate is
only 9.8%. This may be due to the oxidation of the active substance in
the catalyst to metal oxide in the presence of TBHP, and then metal
peroxide oxidizes the sulfide to form sulfoxides. Meanwhile, the TOF in
this work is based on the mol of substrate converted per mol of single
active metal species per hour, and calculated by the formula TOF = n
sulfides removal / (n v8 × h) [34c].
Reusability and stability are important indicators to evaluate cata-
lyst, after each reaction, the catalyst was recovered by centrifugation
◦
and washed several times with CH
2
Cl
2
, and then dried at 80 C for 12 h
before the next selective sulfur oxidation processes. The recyclability of
was studied using phenyl sulfide as substrate (Fig. 4d). After 5 cycles,
Fig. 6. Z-Scan data for V8.
V
8
the catalyst on the sulfur removal still can maintain excellent activity,
and the slight decrease may be due to the loss of the catalyst during the
recycle process. In order to better demonstrate the stability of the re-
3
.5. Two-photon absorption
It is well known that the extended -electron delocalization in the
π
generated V
generated V
8
catalyst, as is shown in Fig. 5, PXRD analysis for the re-
catalyst was studied. At the same time, the catalyst was
structure lead to third-order nonlinear optical response. POMs has
various structures and good electronic properties. It can be used as an
excellent inorganic construction module to participate in molecular
design. Many polyacids modified with charge transfer organic ligands
can enhance their optical properties, which has become a new hotspot in
NLO field [20,41,42]. Therefore, the third-order nonlinear optical
8
impregnated with CH
2
Cl
2
to study its stability in the reaction solvent
catalysts before and after
(
Fig. 5a). It suggests that PXRD for the V
8
reaction were basically consistent, revealing that the structure of V
8
remains intact after the selective sulfur oxidation process.
8
properties of V was researched. Two-photon absorption (TPA) values of
3
.4. IR spectra and PXRD.
As shown in Fig. S3, the peaks at 542 cm can be assigned to
V
8
was measured by open-aperture Z-scanning technique in N, N-
ꢀ
3
ꢀ 1
dimethylformamide solution at a concentration of 1 × 10 mol⋅L
ꢀ 1
ν
(V-O)
under a laser beam with a wavelength of 890 nm. The black dots and the
red solid curves represent experimental and theoretical data, respec-
stretching vibration and the
ν
(V = O) stretching vibration peak is at 996
ꢀ
1
ꢀ 1
cm . The peaks found at 1385 cm stand for the bending vibration of
tively (Fig. 6). The TPA absorption coefficient of V
8
can be calculated as
ꢀ
1
ν
(C
–
H). The peaks at 1641 cm correspond to the bending vibration
0
.001495 cm/GM and the molecular TPA cross section is 573.58 GM.
H). The peak is at 3465 cm 1 is the stretching vibration
ꢀ
peak of
peak of
ν
(N
–
8
The third-order NLO reaction indicated that the petals-shaped V ring
ν
(N
–
H). This is consistent with the literature that has been re-
compound could be used as the third-order NLO material.
ported [22,35–40]. At room temperature, V
and the results are shown in Fig. S4. There are some small gaps in the
data, which may be due to the error of the test instrument and the effect
of the preferred orientation of the powder sample.
8
was measured by PXRD
4
. Conclusions
8
In this work, an eight-membered ring petal-shaped V compound
was synthesized by solvothermal synthesis method. The third-order NLO
property researches show that V is expected to have some applications
in the field of optics. The catalytic performance of this material in sulfur
8
5

Q.-D. Ping et al.
Inorganica Chimica Acta 517 (2020) 120198
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editing. Jia-Nian Li: Writing - review & editing. Ji-Lei Wang: Writing -
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[
[
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