Nano-Co3O4-catalyzed microwave-assisted one-pot synthesis of some seleno [2 , 3-b] pyridine/quinoline derivatives

Article abstract of DOI:10.1007/s11164-021-04478-8

For the efficient synthesis of transition-metal cobalt oxide nanoparticles (Co₃O₄ NPs) without using any costly and toxic solvent or complicated equipment, the co-precipitation method was used in this work. Using scanning electron mi

Full text of DOI:10.1007/s11164-021-04478-8

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-021-04478-8
Nano‑Co3O4‑catalyzed microwave‑assisted one‑pot
synthesis of some seleno [2 , 3‑b ] pyridine/quinoline
derivatives
Yasser Attia Attia1 · Shams H. Abdel‑Hafez2
Received: 20 January 2021 / Accepted: 19 April 2021
© The Author(s), under exclusive licence to Springer Nature B.V. 2021
Abstract
For the efcient synthesis of transition-metal cobalt oxide nanoparticles (Co3O4
NPs) without using any costly and toxic solvent or complicated equipment, the co-
precipitation method was used in this work. Using scanning electron microscopy
(SEM), energy-dispersive X-ray spectroscopy (EDX), UV–Vis spectrophotometry,
Fourier-transform infrared spectroscopy (FTIR) and X-ray difraction (XRD), the
prepared Co3O4 NPs were characterized and identifed. The infuence of prepared
Co3O4 NPs on the developmental synthesis of some selenopyridine/quinoline deriv-
atives under diferent microwave irradiation powers and irradiation times was inves-
tigated via click (reaction) chemistry. The reusable Co3O4 nanoparticles have high
catalytic activity under microwave irradiation for the synthesis of organoselenium
compounds with higher yields (>90%), milder reaction conditions and shorter time
without signifcantly decreasing the reaction rates and yields.
Keywords Co3O4 nanoparticles · Catalysis · Organoselenium compounds · Click
chemistry · Microwave
Introduction
Changes in traditional chemical synthesis and the usage of starting materials with
less toxicity were implemented by the 12 principles of green chemistry [1]. Micro-
wave-assisted organic synthesis (MAOS) demonstrates an efcient, safe, quick, fast
*
*
Yasser Attia Attia
yasserniles@niles.edu.eg
Shams H. Abdel-Hafez
s.abdelhafez@tu.edu.sa
1
2
National Institute of Laser Enhanced Sciences, Cairo University, Giza 12613, Egypt
Department of Chemistry, College of Science, Taif University, P.O. Box 11099, Taif 21944,
Saudi Arabia
Vol.:(0123456789)
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Y. A. Attia, S. H. Abdel-Hafez
and cost-efective method for the synthesis of many organic compounds by means
of highly accelerated reaction rates, reduced reaction time and improved yield
and product quality. In the laboratory, this technology is still underused and has
the potential to have a signifcant efect on the felds of screening, combinatorial
chemistry, medicinal chemistry and drug growth. The traditional methods used for
the synthesis of organic compounds typically involve tedious setup of the appara-
tus, longer heating time and the excessive use of solvents/reagents, resulting in a
higher process cost. The progress of the MAOS presents considerable opportunities
for reducing by-products, waste generation and energy costs. The enhancement of
organic synthesis by microwave irradiation is attributed to its ability to pair directly
with the reaction molecule and to the passing of thermal conductivity, resulting in a
rapid increase in reaction temperature [2, 3].
Organoselenium chemistry has piqued researchers’ interest due to its potential
applications in synthetic chemistry, catalysis and biology, especially since the dis-
covery of the selenocysteine amino acid in mammals. Thus, new organoseleniums
with desired functions are being discovered, as well as newer synthetic methodolo-
gies. Organoselenium compounds also act as an important catalyst for a variety of
organic transformations when activated with hydrogen peroxide/TBHP/halogens or
halogenated organoseleniums [4–15]. Low yield (<15%) of selenopyridine deriva-
tives (9a–c) was obtained in one step from compound (1) after 3 h of refuxing under
conditions of hard reaction with weak chemoselectivity [16–18]. Selenoquinoline
derivatives (10a–c) with yields (40–70%) were also prepared by reaction of chloro-
cyano quinoline derivative (2) with sodium hydrogen selenide followed by aromatic
aldehyde, cycloalkanone and acetic anhydride reactions [19].
Ag/AgCl NPs with diferent shapes have recently been used by Attia and Abdel-
Hafez as nanophotocatalysts to prepare selenopyridine derivatives under visible light
and have been able to achieve a high yield in a short period [20]. Considering the
above-mentioned studies, and in continuation of our previous work which described
the synthesis of substituted seleno pyridine [20], in this work we attempted to estab-
lish an approach to heterocyclic synthesis of seleno (pyridine and quinoline) using
Co3O4 nanocatalyst under microwave irradiation. Because of the increased surface
area-to-volume ratio of nanoparticles, nanocatalysts have shown higher efciencies
or conversion rates with a smaller material mass compared to bulk or even micron-
scale particles [21–28]. The mixed-valence Co3O4 is an important semiconductor of
the magnetic p-type that belongs to the usual spinel crystal structure centered on a
cubic near packing array of oxide ions, whereas the tetrahedral 8a sites are occupied
by Co (II) ions and the octahedral 8a sites are occupied by Co (III) ions the octahe-
dral 16d sites [29].
In addition to the high specifc surface area of Co3O4 NPs than the bulk cobalt
oxide, Co3O4 NPs were found to have interesting magnetic, optical, feld emis-
sion and electrochemical properties that are attractive in system applications when
reduced to the nanometer scale. Transition-metal cobalt oxide (Co3O4) is a very
interesting and promising material due to the presence of mobile oxygen for expan-
sive applications in lithium-ion batteries, gas sensing, data storage, catalysis and
electrochromic devices [30–33]. The unsupported cobalt oxide was used as an active
catalyst in the regulation of air pollution for the reduction of CO [34], NOx [35] and
1 3

Nano‑Co3O4‑catalyzed microwave‑assisted one‑pot…
organic waste stream pollutants [36]. The preparation methods of Co3O4 nanoparti-
cles, including sol–gel [37], reduction/oxidation route [38, 39], thermal decomposi-
tion [40], metal–organic chemical vapor deposition (MOCVD) [41], chemical spray
pyrolysis [42], etc., have been extensively researched [43]. Some of these techniques
are complex and/or require thermal treatment for long periods of time. For the syn-
thesis and manufacture of Co3O4 nanostructures, new methodologies are therefore in
great demand.
In this work, we described a simple method to synthesize Co3O4 nanoparticles to
investigate their catalytic efciency for the synthesis of some seleno [2, 3-b] pyri-
dine/quinoline derivatives under diferent conditions of microwave irradiation.
Materials and methods
All the chemicals from Sigma-Aldrich were collected and used without further puri-
fcation. A Hewlett–Packard 8452A diode-array spectrophotometer reported the
UV–Vis spectrum. X-ray difraction (XRD) measurements were performed using
Cu Ka radiation (k=1.54186 A˚) using a Philips PW1710 X-ray difractometer. The
XRD patterns were reported from 20 to 70° 2H, with a step size of 0.020° 2H and
collecting 10 s per step. With a Zeiss FESEM ULTRA, scanning electron micros-
copy (SEM) images were obtained. A Zeiss FESEM ULTRA Plus (equipped with an
EDX analyzer) microscope with a Philips CM20 microscope, working at an accel-
erating voltage of 200 kV, was being used to obtain scanning electron microscopy
(SEM) images. Based on the Brunauer–Emmett–Teller (BET) model, the precise
surface area and pore volume were calculated using Micromeritics ASAP 2010 to
collect N2 sorption isotherms. The samples were frst outgassed under vacuum at
60 °C overnight, before being examined at 77 K.
Synthesis of Co3O4 NPs
The Co3O4 nanoparticles were produced using the co-precipitation method [28] by
adding 50 mL of NaOH solution (4 M) into 50 mL of CoCl2·6H2O solution (0.2 M)
under vigorous stirring at an approximate rate of 5 mL/min and continued stirring
for 12 h. Then, the collected precipitate was fltered and thoroughly washed with
deionized water three times. The precipitate was dried into fne powder at 100 °C in
an oven and ground using an agate mortar. The powder obtained was calcinated for
2 h at 500 °C.
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Y. A. Attia, S. H. Abdel-Hafez
Microwave‑assisted synthesis of 3‑Amino‑2‑substituted seleno
[2, 3‑b] pyridine (9a; C10H9N3Se), (9b; C16H14N2OSe) and (9c;
C12H14N2O2Se) from 2‑Chloro‑3‑cyano‑4, 6‑dimethylpyridine (1)
General Procedure
A mixture of selenium metal (1 g, 12 mmoles) and sodium borohydride (1.2 g, 32
mmoles) in aqueous ethanol (70%) and chloropyridine derivative 1 (1mmoles) was
added stepwise. The reaction mixture was stirred at room temperature for 15 min;
after that, Co3O4 NPs (0.05 mmol) were added. Then, chloro derivatives of ethyl
acetate, acetonitrile and benzoyl chloride (3 mmoles) were added. The resulting
mixture was irradiated in a microwave reactor for the appropriate time at 80 °C
(power=200 W). The products were collected to give the corresponding products
(9a–c) and recrystallized from ethanol. All spectral data and melting points agreed
with those of the reported compounds [20].
3‑Amino‑4, 6‑dimethylseleno [2, 3‑b] pyridine‑2‑carbonitrile (9a)
m.p. 208–209 ºC (crystallized from ethanol). 1H NMR: δ=2.55, 2.75 (2 s, 6H, 2CH3
pyridine), 6.88 (s, 1H, CH pyridine), 7.28 (s, 2H, NH2) ppm; mass spectra of com-
pounds 6a exhibited molecular ion peak at m/z, (%) 251 (M+ + 1, 100%).
2‑Benzoyl‑3‑amino‑4, 6‑dimethylseleno[2, 3‑b] pyridine (9b)
1
m.p. 250–252 ºC (crystallized from ethanol). H NMR: δ=2.50, 2.70 (2 s, 6H,
2CH3 pyridine), 6.85 (s, 1H, CH pyridine), 7.30 (s, 2H, NH2), 7.55–8.00 (m, 5H,
Ph-H) ppm; mass spectra of compounds 6a exhibited molecular ion peak at m/z, (%)
330 (M+ + 1, 100%).
3‑Amino‑4, 6‑dimethyl‑2‑ethylseleno [2, 3‑b] pyridine carboxylate (9c)
m.p. 155–156 ºC (crystallized from ethanol).1H NMR: δ=1.34 (t, J=9.00 Hz, 3H,
CH3 ester), 2.51, 2.71 (2 s, 6H, 2CH3 pyridine), 4.27 (q, J=7.50 Hz, 2H, CH2), 7.28
(s, 1H, CH pyridine), 5.89 (s, 2H, NH2) ppm; mass spectra of compounds 2 exhib-
ited molecular ion peak at m/z, (%) 298 (M+ + 1, 100%). IR and NMR spectra are
shown in fgures SI (1) and SI (2).
1 3

Nano‑Co3O4‑catalyzed microwave‑assisted one‑pot…
Microwave‑assisted synthesis of 3‑Amino‑2‑substituted seleno
[2 , 3‑b ] quinoline (10a; C13H9N3Se), (10b; C20H17N2OSe) and (10c;
C15H14N2O2Se) from 2‑Chloro‑3‑cyano‑4‑methyl quinoline (2)
General Procedure
A mixture of selenium metal (1 g, 12 mmoles) and sodium borohydride (1.2 g, 32
mmoles) in aqueous ethanol (70%) and chloroquinoline derivative 2 (1mmoles) was
added stepwise. The reaction mixture was stirred at room temperature for 15 min;
after that, Co3O4 NPs (0.05 mmol) were added. Then, chloro derivatives of ethyl
acetate, acetonitrile and benzoyl chloride) (3 mmoles) were added. The resulting
mixture was irradiated in a microwave reactor for the appropriate time at 80 °C
(power=200 W). The products were collected to give the corresponding products
(10a–c) and recrystallized from dioxane. All spectral data and melting points agreed
with those of the reported compounds [19].
3‑Amino‑4‑methyl‑2‑cyanoseleno [2 , 3‑b ] quinoline (10a)
1
m.p.>300ºC (crystallized from dioxane). H NMR: δ=7.90–8.00 (m, 4H Ar–H);
7.40 (s, 2H NH2); 3.20 (s, 3H CH3-quinoline) ppm; mass spectra of compounds 10a
exhibited molecular ion peak at m/z, (%) 286 (M+ + 1, 100%).
3‑Amino‑4‑methyl‑2‑benzoylseleno [2 , 3‑b ]quinoline (10b)
1
m.p. 272–274 ºC (crystallized from dioxane). H NMR: δ=7.60–8.10 (m, 9H
Ar–H); 4.950 (s, 2H NH2); 2.98 (s, 3H CH3-quinoline) ppm; mass spectra of com-
pounds 10b exhibited molecular ion peak at m/z, (%) 366 (M+ + 1, 70%).
3‑Amino‑4‑methyl‑2‑ethylcarboxylateseleno [2 , 3‑b ]quinoline (10c)
m.p. 280–282 ºC (crystallized from dioxane). 1H NMR: δ=7.00–8.51 (m, 4H Ar–H);
6.57 (s, 2H NH2); 4.12 (q, J=7.50 Hz, 2H, CH2); 3.40 (s, 3H CH3-quinoline); (t,
J=9.00 Hz,3H, CH3); mass spectra of compounds 10c exhibited molecular ion peak
at m/z, (%) 333 (M+ − 1, 50%). IR and NMR spectra are shown in fgures SI (1) and
SI (2).
Results
Co3O4 nanoparticles have been successfully synthesized using cobalt chloride
and sodium hydroxide as precursors via the co-precipitation process. SEM has
studied the morphology of Co3O4 nanoparticles. The SEM images of the as-
prepared Co3O4 nanoparticles are represented in Fig. 1a–c. It is apparent from
the SEM picture that the substance consists of extremely fne particles with
1 3

Y. A. Attia, S. H. Abdel-Hafez
Fig. 1 SEM images of the Co3O4 nanoparticles (a-c) and EDX spectrum (d)
sphere-like morphologies that are signifcantly aggregated as clusters because of
the extremely small dimensions and high surface energy of the obtained nanopar-
ticles. The SEM picture shows irregular particles, suggesting that various nano-
particles with a uniform size of 26 2.1 nm make up the synthesized Co3O4. An
energy-dispersive spectrometer (EDS) spectrum on a SEM (Fig. 1d) studied the
chemical composition of Co3O4 NPs. The result shows the O and Co peaks (18.39
wt% and 81.61 wt%), confrming that the sample is of high purity, respectively.
0.5
0.4
0.3
0.2
0.1
8
7
6
5
4
3
2
1
0
a
b
275nm
438nm
300
400
500
600
10
20
30
40
50
60
70
80
Wavelength/nm
2ꢀꢁ/ degrees
Fig. 2 UV–Vis absorption spectrum (a) and XRD patterns of Co3O4 NPs
1 3

Nano‑Co3O4‑catalyzed microwave‑assisted one‑pot…
Figure (2a) displays the UV–Vis spectrum of the prepared Co3O4 NPs. It is
known that Co3O4 NPs with a band gap (~2.7 eV) have a wide visible absorption at
475 nm. Figure 2b displays the XRD patterns of the as-prepared samples showing
difraction peaks of 2θ values at 18.96°, 31.22°, 36.805°, 38.52°, 44.78°, 55.69°,
59.343°, 65.44° and 77.69° corresponding to the crystallographic planes (111),
(229), (311), (222), (400), (422), (511), (440) and (533). These difraction peaks are
in accordance with the stated values (JCPDS Card No. 76–1802) and can be indexed
with a lattice constant of a=8,076 Å [44].
As shown in Fig. 3, the complex’s FTIR spectrum shows the characteristic bands
of the ligands of the NH3 and NO3 groups at approximately 3500–3000, 1600–1500,
1450–1250, 1050 and 650 cm−1 [44]. At approximately 660 and 560 cm−1, two large
bands of the spinel-type Co3O4 structure have been observed. In an octahedral site,
the former band is typical of the Co3 +–O vibration and the latter one is due to the
Co2 + –O vibration in a Co3O4 lattice [45]. The pore volume of Co3O4 NPs is 0.27
(cm3/g), average pore diameter 27.41 (Aº) and specifc surface area 394 (m2/g).
Catalytic activity of Co3O4 NPs for the synthesis
of 3‑Amino‑2‑substituted seleno [2 , 3‑b ] pyridine
and 3‑Amino‑2‑substituted seleno [2 , 3‑b ] quinoline
The efect of the as-synthesized Co3O4 NPs was used and examined on the reaction
of 4,6-dimethyl-2-chloro-3-cyanopyridine (1) and 2-chloro-3-cyano-4-methylquino-
line (2) in the presence of sodium borohydride, Se metal and ClCH2X (X=, –CN,
–COPh and –COOEt) in ethanol using microwave irradiation (200 W) under con-
ventional and non-conventional energy sources (Table 1).
In this synthetic strategy, three seleno [2, 3-b] pyridine derivatives 9a–c
and seleno [2, 3-b] quinoline 10a–c were prepared in the presence of sodium
104
102
100
98
96
94
92
90
88
86
84
82
4000 3500 3000 2500 2000 1500 1000 500
Wavenumber/cm-1
Fig. 3 FTIR spectrum of the prepared Co3O4 NPs
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Y. A. Attia, S. H. Abdel-Hafez
1 3

Nano‑Co3O4‑catalyzed microwave‑assisted one‑pot…
Table 2 The efect of microwave
Power (W)
Products
100
150
200
250
300
power on the synthesis of
compounds 9c and 10c using
Yield %a
9c
10c
68
77
84
90
91
94
92
95
94
97
Co3O4 NPs
aIsolated yields
9c
10c
100
90
80
70
60
100
150
200
250
300
Microwave Power/W
Fig. 4 The efect of microwave power on the yield of compounds 9c and 10c using Co3O4 NPs
borohydride, Se metal and ClCH2X (X = , –CN, –COPh and –COOEt) in ethanol/
water mixture. In the frst set of experiments, when Co3O4 NPs was used as a cat-
alyst in the above-mentioned reaction, compounds 9-10a-c were obtained in (19,
17 and 26%) and (24, 29, and 23%) yield, respectively, under the conventional
condition at room temperature, however, an improvement in the yields of the
obtained products was observed by carrying the reaction under the thermal condi-
tion at 80 °C to yield 9a–c in (41, 45, and 51% ) and 10a–c in (53, 52, and 47%)
yield, respectively, and under visible light irradiation for 2h to yield 9a–c in (71,
76, and 69%) and 10a–c in (67, 73, and 70%) yield, respectively. While by car-
rying the reaction under microwave condition, product 9a–c was aforded in (89,
92, and 91%) yield and 10a–c in (84, 97, and 94%) yield, respectively (Table 1).
This means that when the response was performed via microwave assistance,
the increased catalytic activity of Co3O4 NPs was observed. As shown from the
observations, Co3O4 NPs in the investigated reaction could be used as an efective
heterogeneous nano-catalyst. In addition, when the reaction was conducted under
the microwave condition, the increase in the yield of the products and reduction
in the reaction time to 10 min instead of 24 h were obtained. Based on these
results, we decided to synthesize some of these derivatives in an optimized con-
dition. By the irradiation power from 100 to 300 W, the efect of the microwave
power intensity on the 9–10c product yield was investigated (Table 2 and Fig. 4),
showing that the rise in microwave power at a fxed reaction time contributed to a
1 3

Y. A. Attia, S. H. Abdel-Hafez
Table 3 The efect of microwave
irradiation time on the synthesis
of compounds 9c and 10c at
200 W using Co3O4 NPs
Time (min)
Yield %a
Products
2
4
6
8
10
12
15
9c
10c
38
40
45
66
63
81
78
87
91
94
92
97
94
96
aIsolated yields
relatively higher yield (10 min.), which peaked at 300 W. Thus, to drive the reac-
tion forward, 300 W of microwave irradiation was necessary (Table 2).
The efect of microwave irradiation time on 9–10c product performance was also
investigated by rising the irradiation time to 200 W from 2 to 15 min (Table 3 and
Fig. 5), indicated that the rise in irradiation time has resulted in a relatively higher
yield.
Discussion
The possible explanation for the positive relation between yield and irradiation
power and time is that the increase in thermal microwave efects, fundamentally
based on Arrhenius phenomena, or whether non-thermal microwave efects can
explain these changes, i.e., the efect of radiation from electromagnetic sources.
The two suggested efects are derived from microwave interaction with matter,
heat transfer and distribution along with the sample. As it is derived from the
interaction of electromagnetic radiation with matter that contributes to an energy
coupling at the molecular level, microwave heating is fundamentally distinct from
traditional heating. In addition, since only polar compounds efectively adsorb
microwaves and can convert electromagnetic radiation into heat, it is selective
9c
10c
100
90
80
70
60
50
40
30
0
2
4
6
8
10
12
14
16
Microwave Irrdiation Time/min.
Fig. 5 The efect of microwave irradiation time on the yield of compounds 9c and 10c at microwave
power (200 W) using Co3O4 NPs
1 3

Nano‑Co3O4‑catalyzed microwave‑assisted one‑pot…
and highly dependent on the properties of the material, and volumetric is the
whole volume of the sample heated [46].
The proposed mechanism is based on the reaction of chlorocyano pyridine (1)
and chlorocyano quinoline (2) derivatives with ethylchloro acetate or chloroacetoni-
trile or phenacyl chloride in the presence of sodium borohydride under the same
conditions and gave, frstly, the corresponding intermediate ethyl selenoacetate or
selenoacetonitrile or benzoylseleneo pyridine/quinoline derivative. Secondly, the
intermediate compounds underwent smooth cyclization of Thorpe–Ziegler (as
shown in scheme 1) into the corresponding compound derivatives [47]. The pres-
ence of Co3O4 NPs as nanocatalysts accelerates the reaction and increases the prod-
uct yield by promoting the distribution of microwave heat, which in turn stimulates
the reaction by nucleophilic substitution reaction of NaSeH to form the sodium salt
of the intermediate (3, 4a–c) and removes the chlorine atom in compound (1). Salt
of compound 3 was formed in ethanol and reacted through the SN2 mechanism with
halo acid (Cl–CH2-X) to form the intermediate (5, 6a–c). Subsequent intramolecular
cyclization of Thorpe–Ziegler followed by formation of intermediate (7, 8a–c) to
produce fnal products (9, 10a–c) [48]. A catalyst recovery experiment has been per-
formed to confrm the high stability and catalytic activity of the Co3O4 NPs.
In accordance with the literature method [21, 29], the Co3O4 NPs catalyst was
recovered and reused as a model substrate under the microwave irradiation condition
(200 W and 10 min) in the synthesis of compounds 9–10c. It was observed that the
yields decreased marginally over the fve cycles, suggesting the catalyst’s high sta-
bility, which showed high efciency in relation to the investigated reaction and loss
of operation (Fig. 6).
Conclusion
Co3O4 nanoparticles with a mean particle size of 26 nm were successfully prepared
using the cobalt chloride co-precipitation method with sodium hydroxide. After
characterization in the click reaction, Co3O4 nanoparticles were used to synthesize
several of the seleno [2, 3-b] pyridine/quinoline derivatives under diferent reaction
conditions. It was noted that under microwave conditions, the Co3O4 NPs showed
potential catalytic efciency in excellent production and short reaction time. The use
of water in this reaction as the solvent resulted in a high rate of reaction, yield and
selectivity. In addition, this technique is distinguished by its low cost and environ-
mental friendliness. The results showed that the Co3O4 nanocatalyst in microwave-
assisted organic synthesis (MAOS) has been shown to be an efective heterogeneous
catalyst. This method can be considered as a virgin land for the synthesis of organic
selenium compounds and will be documented in due course in further studies in this
area.
1 3

Y. A. Attia, S. H. Abdel-Hafez
Scheme 1 The proposed mechanism of the production of ethyl carboxylate or carbonitrile or benzoyl
seleno [2, 3-b] pyridine/quinoline derivatives
1 3

Nano‑Co3O4‑catalyzed microwave‑assisted one‑pot…
10c
9c
100
80
60
40
20
0
1
2
3
4
5
Reaction cycle
Fig. 6 Recyclability of Co3O4 NPs in the synthesis of compounds 9c and 10c as model substrate
Supplementary Information The online version contains supplementary material available at https://doi.
org/10.1007/s11164-021-04478-8.
Acknowledgements Taif University Researchers Supporting Project number (TURSP-2020/23), Taif
University, Taif, Saudi Arabia.
Author contributions YAA and SHA conceived and designed research, contributed new reagents or ana-
lytical tools, analyzed data and wrote the manuscript. YAA conducted experiments. All authors read and
approved the manuscript.
Funding This research received a fund from Taif University with project number TURSP-2020/23.
Data availability All data generated or analyzed during this study are included in this published article.
Declarations
Confict of interest The authors declare no conficts of interest.
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