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A Novel Water Soluble Bipyrazolic Tripod Azoic Dye as Chemosensor for Copper (II) in Aqueous Solution

  • Jalal IsaadEmail author
  • Tarik Harit
  • Haad Bessbousse
  • Ahmida El Achari
  • Fouad Malek
Original Article
  • 120 Downloads

Abstract

A novel copper (II) chemosensor based on water soluble azoic dye with bipyrazolic tripod moiety has been synthesized. The spectroscopic data’s of the presented chemosensor and its complex formation with several metal ions are studied in water via colorimetric titrations. The obtained results show that the developed chemosensor presents a high selectivity towards copper (II) in the presence of other metal ions in the typical pH range of biological systems with a detection limit of 0.84 μM.

Keywords

Copper (II) Chemo-sensor Water Bipyrazolic tripod Azo dye 

1 Introduction

Copper is commonly used in a variety of processes because of its malleability, ductility and its effective electrical conductivity. Also, copper is essential to many organisms. This element, along with amino and fatty acids and vitamins are required for normal biochemical processes such as respiration, free radical eradication, energy production, connective tissue formation, oxygen and iron metabolism, maturation of extracellular matrix and neuropeptides, and neuroendocrine signaling biosynthesis and metabolism [1, 2, 3, 4]. Copper is one of the heavy metals which are on the one side, essential for life but on the other, highly toxic to organism such as algae, fungi and many bacteria or viruses. The toxicological effects of the copper can be explained by its interaction with oxygen, sulphur and nitrogen, containing ligands of biological matter to form complexes [5].

The overloading copper (II) (above 11 mg/kg per day) can also be potentially toxic to living cells and causes serious effects on the gastro-intestinal system, inducing strong nausea, vomiting or intestinal bleeding, and also cardiovascular disorders and neuro-degenerative diseases including Alzheimer’s disease [6], Menkes and Wilson diseases [7], prion diseases [8] and familial amyo- trophiclateral sclerosis [9, 10]. Some studies involving animals have also produced lesions on the kidney and liver due to elevated levels of copper [11, 12, 13]. Therefore, and in accordance with toxicity of the copper, the WHO (World Health Organization) recommends 2 mg/L as concentration tolerance of copper in drinking water [14].

The heavy metals detection is considered as a big challenge in the analytical chemistry because of the concentration ranges set by standards and guidelines for reasons of toxicity. Several spectroscopic methods [15, 16, 17, 18] are available to analyze aqueous solutions for both copper, they offer good detection limits and wide linear ranges, but require high cost to be developed for the use in the laboratories.

Actually, various fluorescent and colorimetric [19] molecular probes for copper (II) detection have been reported including dansyl chloride fluorophore [20, 21, 22, 23], BODIPY-based probes [24, 25, 26, 27, 28, 29, 30, 31, 32, 33], Rhodamine based derivatives [34, 35, 36, 37, 38] and azomethine dye [39]. Also, different electrochemical sensors were developed for detecting copper (II) and other metallic cations [40, 41, 42, 43]. All these molecular probes interact selectively with copper (II) ions but in organic solvent which limits their application in aqueous media. Thus, there is still strong demand to develop an efficient copper (II) selective colorimetric probes that can be acted in aqueous medium.

To the best of our knowledge, there are a few studies about the copper (II) chemosensing in water. Therefore, to reduce all limitations cited above, we report herein the synthesis of water soluble colorimetric chemosensor 6 with bipyrazolic tripod as a copper (II) receptor conjugated to an azoic dye glyco-conjugated with two lactose unities through a malonate linker as reported in Fig. 1. The chemical structure of the developed copper (II) chemosensor 6 is taken from the structure of our different chemosensors developed recently and based in the glyco-conjugated dyes with specific receptor to dye different textile materials [44, 45, 46, 47, 48, 49, 50, 51, 52] and detect cyanides [53, 54, 55, 56, 57, 58, 59] and mercury [60] for example in aqueous medium. The interaction in water of the copper (II) cations with the electron-rich donor atoms of the bipyrazolic tripod alters the charge transfer (CT) character of the excited state, and affects the absorption spectral wavelength of the chemosensor 6 producing a cation induced red shift.
Fig. 1

Chemical structure of the chemosensor 6

2 Experimental Procedures

2.1 Materials

The chemical products were used without further purification. Fluka aluminium foils coated with 25 mm particle size silica gel matrix F254 was used for TLC analysis, And their development was involved either UV (254 and 366 nm) or visible light inspection, followed by either treatment with a KMnO4 basic solution or an p-anisaldehyde acid solution and heating. Merck silica gel 60 (particle size 0.040–0.063 nm, 230–400 mesh ASTM) was used for flash column chromatography. Uv–Vis spectra were carried out on a Cary—4000 Varian spectrophotometer, using 1 cm quartz cuvettes. Infra-red spectra were recorded in KBr disk on a Perkin Elmer-Spectrum BX FTIR system. 1H and 13C NMR spectra were recorded at 200 MHz 1H (50.0 MHz 13C) on a Varian Gemini spectrometer. Mass spectra were recorded on a Thermo Scientific LCQ-Fleet mass spectrometer under electrospray ionization (ESI, +c or -c technique). Elemental analyses were carried out on a Perkin Elmer 240C elemental analyzer. The Fe3O4@SILnP catalyst [61, 63, 64] and compounds 4 [47] and 2b [62] were synthetized following our previous papers.

2.2 Synthesis of the Compounds

2.2.1 Synthesis of Diethyl 2-(4-Aminobenzylidene) Malonate (1b)

4-aminobenzaldehyde 1a (1.00 g, 8.27 mmol), diethylmalonate (1.33 g, 8.27 mmol) and the catalyst Na2CaP2O7 (0.1 g) were dissolved in 20 mL of EtOH–water (95/5). The resulting mixture was stirred for 30 min at room temperature. After this time, the reaction solution was filtered to remove the catalyst and washed with AcOEt. The filtrate was then concentrated, and the residue was purified by F.C.C (PE—AcOEt: 2/5) to give compound 1b in 92% as yield. Rf = 0.47. 1H NMR (200 MHz, CDCl3) δ = 8.37 (s, 1H, = CH), 7.61 (d, J = 7.9 Hz, 2H, Ar–H), 6.74 (d, J = 7.9 Hz, 2H, Ar–H), 4.24 (q, J = 8.51 Hz, 4H, CH2), 4.12 (s, 2H, NH2), 1.35 (t, J = 8.51 Hz, 6H, CH3) ppm. 13C NMR (50 MHz, CDCl3) δ = 165.2, 155.4, 148.1, 129.1, 125.6, 120.8, 114.5, 60.8, 13.9 ppm. FTIR (KBr), 3276 cm−1 (v NH), 3062 cm−1 (v CH), 1745 cm−1 (v C=O); MS (ESI): m/z = 264.29 [M+1]+. C14H17NO4 (263.12): C, 63.87; H, 6.51; N, 5.32, found C, 63.98; H, 6.67; N, 5.45.

2.2.2 (diethyl 2-(4-((4-(bis ((3,5-dimethyl-1H-pyrazol-1-yl) methyl) amino) phenyl) diazenyl) benzylidene) malonate (3a)

Compound 1b (1 mmol) and Fe3O4@SILnP (200 mg) were dissolved in a few drops of water. NaNO2 (3 mmol) was added at 0 °C and the resulting mixture was stirred at room temperature for 5 min. After that, aqueous solution of compound 2b (1 mmol) and AcONa (1 mmol) was added and the resulting solution was stirred at room temperature for a few minute. The Fe3O4@SILnP catalyst was magnetically separated and the crude was extracted with chloroform (3 × 10 ml) and purified by recrystallization from ethanol to give compound 3a in 91% as yield. 1H NMR (200 MHz, CDCl3) δ = 7.98–7.94 (m, 7H), 6.91 (d, J = 7.7 Hz, 2H, Ar–H), 6.11 (s, 2H, CH), 5.68 (s, 4H, CH2), 4.22 (q, J = 8.44 Hz, 4H, CH2), 2.44 (s, 6H, CH3), 2.30 (s, 6H, CH3), 1.35 (t, J = 8.44 Hz, 6H, CH3) ppm. 13C NMR (50 MHz, CDCl3) δ = 165.7, 155.7, 151.6, 148.3, 147.4, 143.8, 140.7, 135.2, 128.8, 125.8, 125.1, 122.4, 111.5, 1048, 67.3, 60.6, 14.4, 13.7, 11.2 ppm. FTIR (KBr), 3060 cm−1 (v CH), 1742 cm−1 (v C=O), 1655 cm−1 (v C=N), 1585 cm−1 (v N=N), MS (ESI): m/z = 584.41 [M+1]+. C32H37N7O4 (583.29): C, 65.85; H, 6.39; N, 16.80, found C, 65.97; H, 6.45; N, 16.97.

2.2.3 (4-((4-(bis ((3,5-dimethyl-1H-pyrazol-1-yl) methyl) amino) phenyl) diazenyl) benzylidene)malonic acid (3b)

Dye 3a (0.50 g, 0.86 mmol) in 10 mL of dioxane/water (1/1), was treated with NaOH solution (72 mg, 2.58 mmol) and the resulting solution was stirred at room temperature for 2 h. After this time, the solvent was concentrated and the crude was washed with water and extracted tree times with chloroform (3x10 mL). The aqueous solution was acidified to pH = 7 to afford compound 3b in 88% as yield. 1H NMR (200 MHz, Acetone) δ = 11.10 (s, 2H, COOH), 7.98-7.95 (m, 7H), 6.93 (d, J = 7.8 Hz, 2H, Ar–H), 6.14 (s, 2H, CH), 5.76 (s, 4H, CH2), 2.43 (s, 6H, CH3), 2.32 (s, 6H, CH3) ppm. 13C NMR (50 MHz, CDCl3) δ = 167.3, 159.8, 151.8, 148.5, 147.2, 143.9, 140.7, 135.4, 129.7, 125.8, 125.0, 122.3, 111.7, 104.5, 67.7, 13.2, 11.5 ppm. FTIR (KBr), 3240 cm−1 (v COOH), 3064 cm−1 (v CH), 1771 cm−1 (v C=O), 1652 cm−1 (v C=N), 1584 cm−1 (v N=N), MS (ESI): m/z = 527.23 [M + 1]+. C28H29N7O4 (527.23): C, 63.74; H, 5.54; N, 18.58, found C, 63.87; H, 5.68; N, 18.70.

2.3 Synthesis of Compound 5

Compound 3b (0.20 g, 0.38 mmol) in THF (10 mL) was treated with N-Methyl morpholine (77 mg, 0.76 mmol) and the mixture was stirred at RT for a few minutes. The resulting solution was cooled to 0 °C, and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) (210 mg, 0.76 mmol) was added and the mixture was stirred at RT for 2 h. Then, Compound 4 (386 mg, 0.76 mmol) was added and the reaction solution was stirred at RT overnight. The solvent was evaporated and 30 mL of DCM was added to the obtained residue and washed successively with 20 mL of HCl 5% solution and water (3 × 20 mL). The organic solution was dried with Na2SO4, filtered and concentrated. The residue was purified by F.C.C (EtOAc–petroleum ether, 6:1, Rf = 0.34) to afford 5 in 81% as yield. Mp 97-101 °C. 1H NMR (200 MHz, CDCl3) δ = 7.97–7.94 (m, 7H, Ar–H), 6.94 (d, J = 7.7 Hz, 2H, Ar–H), 6.14 (s, 2H, CH), 5.75 (s, 4H, CH2), 4.60 (d, J = 7.9 Hz, 2 H), 4.53 (dd, J = 6.2, J = 7.8 Hz, 2 H), 4.28 (m, 2 H), 4.19 (m, 2 H), 4.17–3.96 (m, 12 H), 3.77–3.37 (m, 20 H), 2.44 (s, 6H, CH3), 2.33 (s, 6H, CH3), 2.10 (s, 2H, C–OH), 1.40, 1.28, 1.20 (3 s, 36 H) ppm. 13C NMR (50 MHz, CDCl3) δ = 165.4, 154.6, 151.5, 148.4, 147.4, 144.0, 140.5, 135.3, 128.8, 125.7, 125.1, 122.5, 110.1, 109.4, 111.8, 108.5, 106.3, 104.8, 102.6,, 81.6, 79.8, 78.4, 75.6, 74.2, 73.4, 72.1, 71.2, 67.8, 65.3, 62.5, 55.2 [C(OCH3)2], 28.7, 27.4, 26.2, 26.0, 25.3, 24.5, 13.2, 11.4 ppm. FTIR (KBr), 3510 cm−1 (v C–OH), 3060 cm−1 (v CH), 1745 cm−1 (v C=O), 1654 cm−1 (v C=N), 1580 cm−1 (v N=N), MS (ESI): m/z = 1508.86 [M+1]+. C74H105N7O26 (1507.71): C, 58.91; H, 7.02; N, 6.50, found C, 59.07; H, 7.18; N, 6.61.

2.4 Synthesis of chemosensor 6

Compound 5 was treated with 10 mL of TFA 90% aqueous solution for 3 h. Then, the mixture was coevaporated five time with 10 mL of toluene to afford chemosensor 6 (95%) as mixture of α- and β pyranosic anomers in a ratio of 50:50, calculated on the basis of the relative C1 signal intensities. Mp 149–152 °C. 1H NMR (200 MHz, D2O) δ = 7.98–7.94 (m, 7H, Ar–H), 6.95 (d, J = 7.4 Hz, 2H, Ar–H), 6.05 (s, 2H, CH), 5.74 (s, 4H, CH2), 4.87–4.64 (m, 4H, both anomers), 4.36–4.15 (m, 8H, both anomers), 3.96–3.80 (m, 12H, both anomers), 3.46–3.43 (m, 4H, both anomers), 2.43 (s, 6H, CH3), 2.32 (s, 6H, CH3) ppm. 13C NMR (50 MHz, D2O) see Table 1 for the glycidic part and δ = 165.4, 154.7, 151.5, 148.7, 147.3, 144.2, 140.5, 135.4, 128.9, 125.8, 125.2, 122.3, 111.7, 104.5, 67.7, 13.2, 11.6 ppm. FTIR (KBr), 3514 cm−1 (v C–OH), 3062 cm−1 (v CH), 1746 cm−1 (v C=O), 1655 cm−1 (v C=N), 1580 cm−1 (v N=N), MS (ESI): m/z = 1176.57 [M+1]+. C52H69N7O24 (1175.44): C, 53.10; H, 5.91; N, 8.34, found C, 53.24; H, 6.08; N, 8.48.
Table 1

13C NMR spectroscopic data of the glycide portion for the glyco-conjugated dye 6

 

Solvent

C1′

C2′

C3′

C4′

C5′

C6′

C1

C2

C3

C4

C5

C6

α-lactose*

D2O

103.7

72.0

73.5

69.5

76.2

62.0

96.6

74.8

75.3

79.2

75.6

61.1

6 – α

Me2SO

102.4

72.5

73.4

68.7

74.6

67.3

95.8

73.5

74.2

80.4

75.7

60.7

β-actose*

D2O

103.6

72.0

72.5

69.5

76.2

62.0

92.7

72.2

72.4

79.3

71.0

61.1

6 – β

Me2SO

102.7

72.2

72.3

68.5

75.7

67.1

95.6

72.4

72.5

80.6

71.8

60.3

3 Results and Discussion

3.1 Synthesis of Chemosensor 6

The synthesis of the colorimetric chemosensor 6 was carried out in two steps. First, the condensation of 4-aminobenzaldehyde (1a) with dietyl malonate in the presence of Na2CaP2O7 in EtOH–water afford the intermediate 1b. The N-Donor tripodal ligands 2b [60] was prepared via the condensation reaction of the di-substituted 1-(hydroxyl methyl)-3,5- dimethyl pyrazole 2a aniline as primary amine in acetonitrile for 6 h under reflux to afford the expected tripods 2b in high yield. The azoic dye 3a was then prepared by the diazotization of the compound 1b to its corresponding diazonium salt in the presence of Fe3O4@SILnP [62] as green catalyst and a small amount of water and NaNO2. The corresponding diazonium salt was coupled at room temperature with compound 2b to afford the desired dye 3a (Scheme 1).
Scheme 1

synthesis of the derivative 3a. Reagents and conditions. a Na2CaP2O7, EtOH-water, RT, 30 min, b acetonitrile, reflux, 6 h, c Fe3O4@SILnP, small quantity of H2O, NaNO2, 0 C° to RT

The saponification of the diester 3a in the presence of NaOH in dioxane/water mixture provides the diacid derivative 3b witch was coupled with two equivalents of the protected lactose 4 in the presence of DMTMM under basic pH to afford the derivative 5. Finally, the treatment of compound 5 with aqueous solution of TFA at room temperature afford chemosensor 6 as an anomeric mixture as reported in Scheme 2.
Scheme 2

Synthesis of the chemosensor 6. Reagents and conditions. a NaOH, dioxane/water, RT, 2 h. b THF, NMM, DMTMM, 16 h. c TFA 90%, 3 h

The water solubility of the chemosensor 6 was measured at room temperature in water and it was 72.34 g/L.

3.2 UV–Vis Evaluation of Metal Binding Interaction

To investigate the ability of chemosensor 6 to detect copper (II) ions in water, the sensing and optical measurements were performed in water in the presence of K+, Na+, NH4 +, Hg2+, Ni2+, Ba2+, Cr2+, Pb2+, Mn2+, Ag+, Co2+, Al3+, Cd2+, Fe3+, Cu2+, Pd2+, Mg2+, Ca2+, and Zn2+ chlorides salts at pH of 7. The absorption spectrum of chemosensor 6 in water presents a weak band at 366 nm. However, the addition of copper (II) (15 μM) showed a new absorbance peak at 441 nm with color change from colorless to yellow visible to naked eye. On the other hand, no significant changes in the UV spectra of chemosensor 6 were observed in both aqueous solutions when the other metal ions were added as reported in Fig. 2. This result confirm that the chemosensor 6 can be used as a selective colorimetric chemosensor for copper (II) in water.
Fig. 2

Absorption spectra of unchelated chemosensor 6 (15 µM) and upon the addition of various metal ions: K+, Na+, NH4 +, Hg2+, Ni2+, Ba2+, Cr2+, Pb2+, Mn2+, Ag+, Co2+, Al3+, Cd2+, Fe3+, Cu2+, Pd2+, Mg2+, Ca2+, and Zn2+ as the chloride salts (15 μM for Cu2+ and 50 mM for other cations) in water at pH 7

3.3 Selectivity of Chemosensor 6 to Cu2+ Over Other Metal Ions

The interaction of chemosensor 6 with other relevant metal ions was studied by treatment of chemosensor 6 with copper (II) (15 μM) and the absorbance was measured at 441 nm. The resulting solution of chemosensor 6/copper (II) was then treated with other metal ions (50 mM) such as K+, Na+, NH4 +, Hg2+, Ni2+, Ba2+, Cr2+, Pb2+, Mn2+, Ag+, Co2+, Al3+, Cd2+, Fe3+, Cu2+, Pd2+, Mg2+, Ca2+, Zn2+ in competitive conditions and the resulting absorbance was also measured. As reported in Fig. 3, upon the addition of copper (II) ion in the presence of the other metal ions, the coexistent metal ions did not cause any significant absorbance change of chemosensor 6 in aqueous media. Thus, chemosensor 6 could be used as a selective colorimetric sensor for copper (II) in the presence of most competing metal ions.
Fig. 3

Absorbance spectral changes of competitive selectivity of chemosensor 6 (0.5 mg/ml) in water upon the addition of 15 μM copper (II) in the presence of 50 mM of at pH 7, background metal ions (K+, Na+, NH4 +, Hg2+, Ni2+, Ba2+, Cr2+, Pb2+, Mn2+, Ag+, Co2+, Al3+, Cd2+, Fe3+, Cu2+, Pd2+, Mg2+, Ca2+, and Zn2+)

The observed color changes of the chemosensor 6 upon addition of copper (II) can be explained by the participation of the electron-donor aniline nitrogen in the copper (II) ion ligation which promoted intra-molecular charge-transfer (ICT) processes. In fact, the nitrogen is a middle intensity base and copper (II) is the borderline acid according to the hard–soft acid–base theory, therefore copper (II) could form its most stable complex with nitrogen within the macrocycle. The possible structure of a 1:1 complex of chemosensor 6 with copper (II) is shown in Scheme 3.
Scheme 3

The proposed binding mode of chemosensor 6 with copper (II) and the sensing mechanism (R = lactose)

On the other hand, the absorption of chemosensor 6 increases with 1 equivalent of copper (II). However, the 1 equivalent of EDTA addition produces a disappearance of the yellow color and a significant absorption increasing (Fig. 4).
Fig. 4

Colorimetric changes of chemosensor 6 (15 µM) after the sequential addition of copper (II) and 1 eq of EDTA in water at pH = 7

The addition of copper (II) to this solution, the recovered absorption was effectively increased again. This result shows that In addition, copper (II) sensing by the chemosensor 6 is reversible.

3.4 The pH Effect

The pH effect on the chemosensing activity of the chemosensor 6 toward copper (II) ions was also investigated. The obtained results reported in Fig. 5 showed that the chemosensor 6 was performing over a pH range of 6 to 8. Hence, chemosensor 6 is suitable to be used as copper (II) chemosensor in biological systems.
Fig. 5

Relative absorption of chemosensor 6 (15 µM) upon the addition of 25 μM of copper (II) ion in water at pH values of 6, 7 or 8

3.5 Binding Analysis for Chemosensor 6—Copper (II)

The binding stoichiometry of chemosensor 6 with copper (II) ions was calculated by absorbance spectra analysis using a Job’s plot. As reported in Fig. 6, the absorbance maximum value of chemosensor 6—copper (II) was achieved at a mole fraction of approximately 50% of copper (II) ions which suggests that the most plausible binding stoichiometry ratio of compound 6 with copper (II) ions is 1:1.
Fig. 6

Job’s plot of chemosensor 6 with copper (II) ions in water at pH = 7. Total concentration of 10 μM, λabs = 441 nm

As reported in Fig. 7, the plotting 1/ΔA against 1/[Cu2+] was used to calculate the association constant Ka. The obtained data’s has a linear appearance according to the Benesi-Hilderbrand equation, and the Ka value obtained from the slope and intercept of the line, was found to be 2.26.103 M−1.
Fig. 7

Benesi-Hildebrand plot of the chemosensor 6/copper (II) complex in water

The detection limit (DL) of the chemosensor 6 as a colorimetric sensor for the analysis of copper (II) was evaluated from the plot of absorbance intensity as a function of the copper (II) concentration (Fig. 8). The chemosensor 6 DL was calculated by using the following equation:
$$ {\text{DL }} = {\text{ Sb}}_{ 1} /{\text{S }} \times {\text{K}} .$$
Fig. 8

Calibration curve of chemosensor 6 (15 µM)/copper (II) in water

K = 3; Sb1 is the blank solution standard deviation, S is the calibration curve slope.

It was found that the chemosensor 6 have a detection limit of 0.84 μM which is comparable to the previously published spectrophotometric methods as summarized in Table 2.
Table 2

Analytical features of the reported spectrophotometric methods for the copper II determination

Reagents

DL (μM)

Reference

BODIPY modified silica coated magnetite nanoparticles

1

[64]

A lawsone azo dye

0.27

[65]

2-aminobenzamide azo dye

Micromolar

[66]

azo-phenol derivative probe

20

[67]

3.6 Real Sample Analyses

Proposed chemosensor 6 could successfully recover copper (II) ion from tap water containing different amount of copper ions. Different amounts of copper (II) were spiked with water solution and measured. The obtained results were showed good selectivity in the Table 3.
Table 3

Determination of copper ion in water samples solution

Zn(II) (mg L−1)

Recovery (%)

Added

Found

15

15.21 ± 0.05

101.4

20

19.89 ± 0.06

99.45

30

30.17 ± 0.05

100.56

In conclusion, a novel water soluble chemosensor for copper (II) in water has been synthesized. The developed chemosensor presents a high selectivity towards copper (II) in the presence of different metal ions in biological systems with a detection limit of 0.84 μM.

Supplementary material

42250_2018_28_MOESM1_ESM.docx (179 kb)
Supplementary material 1 (DOCX 179 kb)

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Copyright information

© The Tunisian Chemical Society and Springer Nature Switzerland AG 2018

Authors and Affiliations

  • Jalal Isaad
    • 1
    • 3
    Email author
  • Tarik Harit
    • 2
    • 3
  • Haad Bessbousse
    • 4
  • Ahmida El Achari
    • 5
  • Fouad Malek
    • 2
    • 3
  1. 1.Faculté Des Sciences & Techniques d’Al Hoceima, Laboratoire R&D en sciences de l’ingénieurAjdirMorocco
  2. 2.Faculté des Sciences d’Oujda, Laboratoire de Chimie Organique, Macromoléculaire & Produits NaturelsOujdaMorocco
  3. 3.Université Mohamed 1erOujdaMorocco
  4. 4.Entité minéralurgie et procédé de traitementOCP SAKhouribgaMorocco
  5. 5.Lille Nord de France University, Engineering and Textile Materials LaboratoryRoubaixFrance

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