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Synthesis, optical and structural characterisation of ZnS nanoparticles derived from Zn(ii) dithiocarbamate complexes

  • Damian C. Onwudiwe EMAIL logo , Jerry O. Adeyemi , Rebecca T. Papane , Felicia F. Bobinihi and Eric Hosten
Published/Copyright: November 20, 2021
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Open Chemistry
From the journal Open Chemistry Volume 19 Issue 1

Abstract

Zinc sulphide nanoparticles represented as ZnS1, ZnS2 and ZnS3 have been prepared from Zn(ii) N-methyl-N-ethanoldithiocarbamate (1) complex and its 2,2′-bipyridine (2) and 1,10′-phenanthroline (3) adducts, respectively. Both the parent complex (1) and the adducts (2) and (3) were characterised by spectroscopic techniques and elemental analysis. In the solid state, the structures of complexes (1) and (2) were established using single-crystal X-ray analysis. Complex (1) possessed a distorted trigonal bipyramidal geometry about the zinc centre, whilst forming a dimer via bidentate bridging coordination between two opposite dithiocarbamate motifs. On the other hand, complex (2) formed a trigonal prismatic geometry about the Zn centre with a ZnS4N2 chromophore. The decomposition of the complexes in hexadecylamine afforded spherical-shaped ZnS nanoparticles of the cubic sphalerite crystal phase. The transmission electron microscopy (TEM) micrographs showed that the average particles size of ZnS1, ZnS2 and ZnS3 were 2.63, 5.27 and 6.52 nm, respectively. In the optical study, the estimated bandgap energies were found in the range between 4.34 and 4.08 eV, which indicated a blue shift when compared with the bandgap energy of bulk ZnS.

Graphical abstract

Keywords: dithiocarbamate; ZnS nanoparticles; crystal structure; optical properties

1 Introduction

Group 12 complexes of dithiocarbamate have been vastly studied due to their usefulness in areas such as analytical chemistry and agriculture, as well as their use as precursor compounds for material synthesis [1]. Zinc(ii) dithiocarbamate is prominent amongst this class of complexes and has found relevance in many industrial and biological processes [2,3]. Both the centrosymmetric dimeric [4] and the monomeric structures, such as those derived from N-isobutyl-N-propyl and N-cyclohexyl-N-methyl dithiocarbamate [5,6], have been reported for Zinc(ii) dithiocarbamate complexes. This variation is indicative of the influence of the nature of organic substituent present in the dithiocarbamate backbone on the observed structure of the complexes in a solid state [4].

Transition metal chalcogenides are important semiconductor materials that have continued to draw attention due to their outstanding properties and wide range of applications in diverse areas [7]. Specifically, zinc sulphide (ZnS) is a II–VI semiconductor that has continued to gain more attention owing to industrial, biological and agricultural applications [8]. The nanoparticles show significant quantum confinement effects that influence their optical and electrical properties [9]. Hence, its application in photovoltaics, photonic/optoelectronic devices, sensors and catalysis [10,11]. It is more chemically stable when compared with ZnSe, which in turn favours its preferred usage as host material [12]. Its polymorphic nature implies that it exists in two crystalline forms of wurtzite and sphalerite (zinc blend) [12]. However, the coordination geometry between S and Zn remains tetrahedral in nature. The difference, notwithstanding, is that the wurtzite phase has a hexagonal form whereas the sphalerite phase possesses a stable cubic form [12]. The bandgap energy found in both polymorphs is 3.91 and 3.54 for the wurtzite and zinc blend, respectively [12]. ZnS has been prepared by different methods in other to achieve specific structures and properties [9], and different chemical and physical methods have been reported for the synthesis of ZnS [13,14]. Earlier, it has been mostly prepared using precipitation or coprecipitation methods [15,16]. However, in recent times, the single-source precursor methods have been widely used and Zn(ii) complexes have been utilised as precursor compounds for the preparation of ZnS nanoparticles [17,18]. The thermal decomposition of compounds bearing S-donor groups has proven to be a desirable route to achieving ZnS nanoparticles with good crystallinity, tuneable dimensions and narrow size distributions [9]. The ease of synthesis of metal sulphide (MS) nanoparticles from metal dithiocarbamate complexes as precursor compounds has made them desirable starting materials in nanomaterial synthesis.

Herein, we present the synthesis, structural and optical properties of ZnS nanoparticles derived from Zn(ii) bis(N-methyl-N-ethanoldithiocarbamate) (1) and its 2,2′-bipyridine (2) and 1,10′-phenanthrolin (3) adducts.

2 Experimental

2.1 Materials and physical measurements

All reagents used in this study were of analytical grade, were purchased from Sigma-Aldrich chemicals company and were used without any further purifications. These include N-methyl-N-ethanolamine, carbon disulphide, ammonium hydroxide, zinc acetate dihydrate, chloroform, 2,2′-bipyridine, 1, 10′-phenanthroline, trioctylphosphine (TOP), hexadecylamine, methanol and toluene. The percentage elemental composition (C, H, N and S) of the complexes was estimated using an Elementar analyser, Vario EL Cube. Infrared spectra, obtained at room temperature, were carried out on Alpha Bruker FTIR spectrophotometer in the wavenumber range of 4,000–500 cm−1. The Nuclear Magnetic Resonance (NMR) spectra were recorded on a 600 MHz Bruker Avance III NMR spectrometer for 1H and 13C NMR analysis in chloroform solution (CDCl3) solution. Powder X-ray diffractogram (XRD) of the nanoparticles was recorded on a Bruker D8 Advanced XRD machine, equipped with a proportional counter using Cu Kα radiation (λ = 1.5405 A, nickel filter). Samples were added on a flat steel sample holder and scanned from 10 to 80°C. The diffraction peaks at several values were matched with other recorded standards in JCPDS. Ultraviolet-visible (UV-vis) spectra of the nanoparticles were recorded using a Perkin-Elmer λ20 UV-vis spectrophotometer. The photoluminescence (PL) spectra of the nanoparticles were measured using Perkin Elmer LS 45 Fluorimeter.

2.1.1 Single crystal X-ray determination

Single crystal X-ray diffraction analyses were performed at 200 K using a Bruker Kappa Apex II diffractometer with monochromated Mo Kα radiation (λ = 0.71073 Å). APEX2 [19] was used for data collection and SAINT [19] for cell refinement and data reduction. The structure was solved using SHELXT-2014 [20] and refined by least-squares procedures using SHELXL-2016 [21] with SHELXLE [22] as a graphical interface. Data were corrected for absorption effects using the numerical method implemented in SADABS [19]. All non-hydrogen atoms were refined anisotropically. Carbon-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with U iso(H) set to 1.2U eq(C). The H atoms of the methyl groups were allowed to rotate with a fixed angle around the C–C bond to best fit the experimental electron density (HFIX 137 in the SHELX program suite [21]) with U iso(H) set to 1.5U eq(C). The methyl groups of (1) show rotational disorder with two positions rotated from each other by 60 degrees. The H atoms of the methyl groups were allowed to rotate with a fixed angle around the C–C bond to best fit the experimental electron density (HFIX 123 in the SHELX program [21]). The H atoms of the hydroxyl groups were allowed to rotate with a fixed angle around the C–O bond to best fit the experimental electron density (HFIX 147 in the SHELX program [21]), with U iso(H) set to 1.5U eq(O). The structure of (2) was refined as a 2-component twin with a BASF parameter of 0.25.

2.2 Synthesis of ammonium-N-methyl-N-ethanoldithiocarbamate

The synthesis of this ligand followed an already reported synthetic route [23]. Briefly, an equimolar amount of N-methyl-N-ethanolamine (0.8 mL, 0.001 mol) and carbon disulphide (0.6 mL, 0.001 mol) was stirred for 30 min in a round bottom flask placed in an ice bath. To this mixture, ammonium hydroxide (3 mL, 0.001 mol) was added and stirred further for 2 h to obtain the ammonium salt of N-methyl-N-ethanoldithiocarbamate.

2.3 Synthesis of Zn(ii) bis(N-methyl-N-ethanoldithiocarbamate) (1)

A freshly prepared ammonium N-methyl-N-ethanoldithiocarbamate (1.8 g, 0.005 mol) was dissolved in 20 mL water, followed by the addition of 20 mL aqueous solution of zinc acetate dihydrate (1.2 g, 0.005 mol) with continuous stirring for an hour. The obtained white precipitate was filtered, rinsed with a large volume of water and dried [23], as shown in Scheme 1.

Scheme 1 Synthesis of (a) ammonium N-methyl-N-ethanoldithiocarbamate and (b) Zn(ii) bis-(N-methyl-N-ethanoldithiocarbamate).
Scheme 1

Synthesis of (a) ammonium N-methyl-N-ethanoldithiocarbamate and (b) Zn(ii) bis-(N-methyl-N-ethanoldithiocarbamate).

(1): Yield, 1.25 g, 78%; M. Pt, 112–113°C; selected IR, (cm−1): 1,492 ν(C═N), 1,387 ν(C2–N), 977 ν(C–S), 2,930 ν(–C–H), 3,287 ν(O–H), 1,619 δ(O–H), 503 (Zn–S); 1H NMR (CDCl3) δ (ppm) = 4.85 (s, 2H, NCH2CH2OH), 3.89 (t, 4H, NCH2CH 2OH), 3.51 (s, 6H, NCH 3), 3.35 (t, 4H, NCH 2CH2OH); 13C NMR (CDCl3) δ (ppm) = 206.2 (–NCS2), 66.0 (NCH2 CH2OH), 60.2 (NCH2 CH2OH), 44.9 (NCH3); anal. calc. for C8H16N2S4 (365.87): C, 26.26; H, 4.41; N, 7.66; S, 35.06. Found: C, 26.12; H, 4.22; N, 7.99; S, 35.02%.

2.4 Synthesis of 2,2′-bipyridine (2) and 1, 10′-phenanthroline (3) adducts of Zn(ii) bis(N-methyl-N-ethanoldithiocarbamate)

The procedure followed an already reported method [24]. A hot 20 mL chloroform solution of the Lewis base (0.001 mol) (either 2,2′-bipyridine (2) or 1,10′-phenanthroline (3)) was added to an equimolar amount of hot 20 mL chloroform solution of Zn(ii) bis(N-methyl-N-ethanoldithiocarbamate) (1) (0.37 g, 0.001 mol) while stirring. The resulting yellow solution was refluxed for 1 h, then allowed to cool to room temperature and filtered. The yellow filtrate from the solution was kept for crystallisation by slow evaporation. Scheme 2 presents the synthetic route for the formation of the adducts.

Scheme 2 Synthesis of (a) Zn(ii) (2,2′-bipyridyl) bis(N-methyl-N-ethanoldithiocarbamate) (2) and (b) Zn(ii) (1,10-phenanthroline) bis(N-methyl-N-ethanoldithiocarbamate) (3).
Scheme 2

Synthesis of (a) Zn(ii) (2,2′-bipyridyl) bis(N-methyl-N-ethanoldithiocarbamate) (2) and (b) Zn(ii) (1,10-phenanthroline) bis(N-methyl-N-ethanoldithiocarbamate) (3).

(2): Yield, 0.98 g, 69%; M. Pt, 163–165°C; selected IR, (cm−1): 1,475 ν(C═N), 1,367 ν(C2–N), 977 ν(C–S), 2,920 ν(–C–H), 3,377 ν(O–H), 1,597 δ(O–H), 506 (Zn–S); 1H NMR (CDCl3) δ (ppm) = 8.93–7.25 (m, 8H, bpy), 5.35 (s, 2H, NCH2CH2OH), 4.07 (t, 4H, NCH2CH 2OH), 3.93 (t, 4H, NCH 2CH2OH), 3.52 (s, 6H, NCH 3); 13C NMR (CDCl3) δ (ppm) = 204.2 (–NCS2), 163.5, 136.2, 129.4, 128.9, (bpy), 54.1 (NCH2 CH2OH), 32.0 (NCH2CH2OH), 25.9 (NCH3); anal. calc. for C18H24N4S4 (522.05): C, 41.41; H, 4.63; N, 10.73; S, 24.57. Found: C, 41.32; H, 4.61; N, 11.10; S, 24.22%.

(3): Yield, 1.05 g, 74 %; M. Pt, 172–173°C; Selected IR, (cm−1): 1,481 ν(C═N), 1,376 ν(C2–N), 981 ν(C–S), 2,918 ν(–C–H), 3,327 ν(O–H), 1,580 δ(O–H), 497 (Zn–S); 1H NMR (CDCl3) δ (ppm) = 9.57–7.20 (m, 8H, phen), 5.34 (s, 2H, NCH2CH2OH), 4.25 (t, 4H, NCH2CH 2OH), 3.69 (t, 4H, 4H, NCH 2CH2OH), 3.16 (s, 6H, NCH 3); 13C NMR (CDCl3) δ (ppm) = 204.5 (–NCS2), 127.3, 129.2, 132.5, 159.8 (phen), 53.7 (NCH2 CH2OH), 26.0 (NCH3), 31.2 (NCH2CH2OH); anal. calc. for C20H24N4S4 (546.0702): C, 43.99; H, 4.43; N, 10.26; S, 23.49. Found: C, 44.12; H, 4.31; N, 4.55; S, 23.02%.

2.5 Synthesis of hexadecylamine (HDA) capped ZnS nanoparticles

The nanoparticles were prepared with slight modifications of an established solvothermal procedure, using a single-source precursor [25,26]. About 0.3 g of the complexes was dispersed in 5 mL of trioctylphosphine (TOP) and injected into a solution of 3 g hot hexadecylamine at 160°C, with vigorous stirring under nitrogen. The reaction temperature was maintained at 160°C while aliquots were taken at 15, 30 and 45 min, to monitor the growth of nanoparticles. After 60 min, the heating was stopped and the solution was allowed to cool to 70°C, then excess methanol was added to precipitate the nanoparticles. The solid was separated by centrifugation and re-dispersed in toluene. The centrifugation and isolation procedure were repeated three times for the purification of nanoparticles. The synthesised nanoparticles were represented as ZnS1, ZnS2 and ZnS3, to denote the particles synthesised from (1), (2) and (3), respectively.

3 Results and discussion

3.1 Description of crystal structures of (1) and (2)

The molecular structures of complexes (1) and (2) were established by single-crystal X-ray diffractometry. Crystallographic parameters for (1) and (2) were obtained and the selected bond angles and distances have been summarised in Tables 1 and 2. The complexes reveal a chelating k 2 -S,S′ binding fashion of dithiocarbamates, which is the most common structural motif [27]. The ORTEP diagrams of complexes (1) and (2) are presented in Figures 1 and 2, respectively. Both complexes are monoclinic with P21/n and Pn space groups for complexes (1) and (2), respectively.

Table 1

Summary of crystal data and structure refinement

Complex (1) (2)
Empirical formula C16H32N4O4S8Zn2 C18H24N4O2S4Zn
Formula weight 731.72 522.04
Crystal size (mm) 0.13 × 0.15 × 0.58 0.07 × 0.40 × 0.54
Crystal system Monoclinic Monoclinic
Temperature (K) 200 200
Crystal habit Rod, colourless Plate, clear yellow
Space group P21/n Pn
a (Å) 8.4252(2) 10.5377(6)
b (Å) 22.1700(7) 6.7318(3)
c (Å) 8.4854(3) 16.0866(9)
α (°) 90 90
β (˚) 113.496(1) 103.132(2)
γ (°) 90 90
V [Å**3] 1453.55(8) 1111.30(10)
Z 2 2
Dcalc (Mg m−3) 1.672 1.560
F(000) 752.0 540
Dataset −11:10; −29:29; −11:11 −14:14; −8:8; −21:21
μ(MoKa) (/mm) 2.255 1.503
R(int) 0.024 0.0426
Observed reflections I  >  2σ(I) 3,160 5,011
Nref, Npar 3631,156 5391,267
Final R, wR2, S 0.0217, 0.0516, 1.05 0.0637, 0.1716, 1.10
Max. residual density [e/Å3] 0.26 2.26
Min. residual density [e/Å3] −0.34 −0.76
θ range (˚) 1.8–28.3 2.1–28.3
Table 2

Selected bond lengths and bond angles

(1) (2)
Bond lengths (Å) Bond lengths (Å)
Zn1–S11 2.3332(5) Zn1–S11 2.516(3)
Zn1–S12 2.4488(6) Zn1–S12 2.577(3)
Zn1–S21 2.3391(4) Zn1–S21 2.523(3)
Zn1–S22 2.8608(6) Zn1–S22 2.559(3)
Zn1–S22i 2.3659(5) Zn1–N31 2.172(8)
S22–Zni 2.3659(5) Zn1–N32 2.197(8)
S11–C11 1.7350(16) S11–C11 1.713(12)
S12–C11 1.7125(17) S12–C11 1.720(12)
S21–C21 1.7138(14) S21–C21 1.705(10)
S22–C21 1.7491(15) S22–C21 1.734(11)
N1–C11 1.327(2) N1–C11 1.340(15)
N2–C21 1.3215(19) N2–C21 1.440(16)
Bond angle (°) Bond angle (°)
S11–Zn1–S12 76.19(2) S11–Zn1–S12 70.38(9)
S11–Zn1–S22 94.76(2) S11–Zn1–S21 94.24(10)
S11–Zn1–S22i 123.49(2) S21–Zn1–S22 71.00(9)
S21–Zn1–S22 68.85(2) S12–Zn1–S22 96.61(10)
S21–Zn1–S22i 108.45(2) S11–Zn1–N32 94.1(2)
S12–Zn1–S21 102.58(2) S12–Zn1–N32 104.0(2)
S22–Zn1–S22i 93.45(2) S21–Zn1–N31 105.1(2)
Zn1–S11–C11 84.50(6) S22–Zn1–N31 94.0(2)
Zn1–S12–C11 81.42(5) N31–Zn1–N32 74.7(3)
Zn1–S21–C21 95.14(5) Zn1–S11–C11 87.0(4)
Zn1–S22–C21 77.79(5) Zn1–S12–C11 84.9(4)
Zn1–S22–Zn1i 86.55(2) Zn1–S21–C21 86.1(4)
C11–N1–C12 121.15(16) Zn1–S22–C21 84.3(3)
C11–N1–C13 122.03(14) C11–N1–C12 122.9(10)
C12–N1–C13 116.79(16) C11–N1–C13 122.7(9)
C21–N1–C23 123.81(13) C12–N1–C13 114.4(10)
C22–N1–C23 115.27(12) C21–N1–C22 119.8(9)
C21–N1–C22 120.91(13) C21–N1–C23 123.2(10)
S12–C11–N1 121.21(12) C22–N1–C23 117.0(9)
S11–C11–N1 121.00(13)
S21–C21–N2 120.36(11)
S22–C21–N2 121.36(11)
S11–C11–S12 117.79(9)
S21–C21–S22 118.18(8)

Symmetry elements: (i) 1 − x, 1 − y, 2 − z.

Figure 1 (a) The molecular structure and (b) packing diagram of [ZnL1 2] with displacement ellipsoids drawn to 50% probability level. Symmetry elements: (i) 1 − x, 1 − y, 2 − z.
Figure 1

(a) The molecular structure and (b) packing diagram of [ZnL1 2] with displacement ellipsoids drawn to 50% probability level. Symmetry elements: (i) 1 − x, 1 − y, 2 − z.

Figure 2 (a) The molecular structure and (b) packing diagram viewed normal to (010) of (2) with displacement ellipsoids drawn to 50% probability level.
Figure 2

(a) The molecular structure and (b) packing diagram viewed normal to (010) of (2) with displacement ellipsoids drawn to 50% probability level.

Complex (1) is a centrosymmetric dimeric structure in which an asymmetric unit of one contains two half binuclear molecules, such that the centre of inversion of each unit is inclined towards another as shown in Figure 1. A typical feature of dithiocarbamate compounds is the planarity [28] of the MS2CNC2 unit, and all these seven atoms were found approximately in a plane, which resulted in the stereochemical rigidity of the dithiocarbamate [29]. Owing to the presence of the two chelating and bridging dithiocarbamate ligands, each independent complex contains a core central eight-membered ring of ZnSCS2, which is stabilised by a trans-annular Zn–S22 bond that is longer by approximately 0.5 Å than the other Zn–S bonds. This feature is in agreement with those reported already earlier [30,31,32]. In each mononuclear moiety of (1), the dithiocarbamate ligands featured an S,S′-anisobidentate coordination, in which each of them contains a short Zn–S bonds (Zn1–S11/Zn1–S21) and a longer Zn–S bonds (Zn1–S12/Zn1–S22), Table 2 [33]. Although there are some conformational differences amongst each binuclear moiety of (1) complex as regards the terminal residues, the Zn2S8 molecular cores are superimposable. The longer Zn–S bond interactions and the acute chelate angles seemed to be the major contributors to the distortion of the 4 + 1 coordination geometry. Therefore, the geometry around the Zn atoms was distorted trigonal bipyramidal with about 35% along the Berry pseudorotation and S22i (i: 1 − x, 1 − y, 2 − z) as the pivot atom [34]. Tau-Descriptor for the 5-coordination is 0.57 [35].

Furthermore, in complex (1), the bond parameters of the terminal dithiocarbamate attached to the central Zn atom; S11–Zn1–S12 [76.19(2)°] and S21–Zn1–S22 [68.85(2)°] deviate significantly from 90o, which consequently results in the distortion of the geometry about the Zn centre due to the small bite angle. In addition, other S–Zn–S bonds angles in (1) were found at 102.58(2)° and 94.76(2)° for S12–Zn–S21 and S11–Zn–S22, respectively. It is expected that atoms at the equatorial position should be close to 120o. However, due to steric hindrances, these angles were smaller for S12–Zn–S21 and S1–Zn–S4 in (1). Furthermore, in complex (1), the chelating and bridging behaviour of the dithiocarbamate ligands were observed due to dimerisation through the coordination of two Zn atoms and S atoms, similar to earlier reported cadmium dithiocarbamate [27]. Despite the varying bond angles around the eight-membered ring of [ZnSCS]2, a stable boat and chair conformation was observed in this complex. This was in agreement with Tiekink and Zukerman–Schpector report [4,36]. In the chelating ring, the C–S bond lengths were between those of double and single bonds (Table 2) contrary to a typical C–S bond length of 1.81Å, which appeared higher than the average length found in this complex [1.72Å] [33]. This indicated a double bond character and further signified the charge delocalisation within the CS2Zn chelate ring [27]. Both intra and intermolecular C–H/S and O⋯HO interactions existed, as shown in Table 3. One of the ethanolic groups in the dithiocarbamate moiety was disordered on each monomer unit of the complex.

Table 3

Geometric details of hydrogen bonding (°) and (Å)

Interactions D–H H⋯A D⋯A D–H⋯A
(1)
O1–H1··O2 0.8400 1.9500 2.7614(18) 163.00
O2–H2··O1 0.8400 1.8800 2.7130(18) 171.00
C12–H12D··S12 0.9800 2.4200 2.981(2) 116.00
C12–H12F··S12 0.9800 2.6900 3.6398(16) 164.00
C13–H13B··S11 0.9900 2.6700 3.0079(18) 100.00
C14–H14A··S11 0.9900 2.8600 3.4256(18) 117.00
C14–H14B··S12 0.9900 2.8500 3.7715(19) 156.00
C22–H22D··S21 0.9800 2.3800 2.9529(16) 116.00
C23–H23B··S22 0.9900 2.5800 3.0654(16) 110.00
(2)
O2–H2··N2 0.8400 2.5700 2.893(15) 104.00
C12–H12C··S12 0.9800 2.5100 3.058(15) 115.00
C13–H13B··S11 0.9900 2.6100 2.986(13) 102.00
C22–H22C··S21 0.9800 2.5800 2.969(13) 104.00
C23–H23B··S22 0.9900 2.5900 3.026(12) 106.00
C314–H314··O1 0.9500 2.5700 3.520(15) 176.00
C315–H315··S21 0.9500 2.7900 3.497(11) 132.00
C315–H315··S22 0.9500 2.8200 3.481(11) 128.00
C325–H325··S12 0.9500 2.7900 3.582(10) 3.582(10)

In complex (2), the Zn atom was bonded to the dithiocarbamate ligands through the two sulphur atoms and to the 2,2′-bipyridine through two nitrogen atoms of the Lewis base, to form a ZnS4N2 group in both complexes. Owing to the closeness of Zn to the bipyridine molecule in [ZnL2 (bpy)] complex, an appreciable difference in the bond lengths between the Zn and S bonds was observed like those in complex (1). The occurrence of shorter bond lengths (which are longer than the shorter Zn–S bond in (1)) was observed for the Zn1–S11 and Zn1–S21, while those of longer length, Zn1–S12 and Zn1–S22, were lesser than those found in (1). This gave a trigonal prism geometry around the Zn atom similar to the previous report [27]. The atoms S11, S12 and N32, and S21, S22 and N31 define the bases of the prism with the Zn atom situated 1.351(4) and 1.323(5) Å from the prism bases, respectively. The bite angles observed in each of the dithiocarbamate groups in (2): S11–Zn1–S12 [70.38(9)°] and S21–Zn1–S22 [71.00(9)°] were comparable to the values found for other bipyridine adducts of dithiocarbamate [27]. The bite angle of the bipyridine molecule in the complexes was 74.7(3)° and was slightly larger than the observed angle in bipyridine adducts of similar N-alkyl-N-phenyl dithiocarbamate complexes containing cadmium atoms [37]. The intra- and intermolecular C–H/S and O⋯HO interactions existed, as shown in Table 3. Due to the closeness of the Zn to the bipyridine molecule, an appreciable difference in the bond lengths between the Zn–S bonds was observed. Both complexes have two molecules per unit cell as shown in the packing diagram in Figures 1b and 2b.

3.2 1H and 13C NMR spectroscopy of the complexes

In the 1H NMR spectra of the precursor complex and the adducts, the protons of the methyl group attached to the electronegative nitrogen atom from the ligand moiety resonated as a singlet in the range 3.52–3.16 ppm. This was somewhat higher than expected for a free methyl proton due to its attachment to an electronegative atom [23]. Signals of methylene protons from the ethanolic group attached to both N- and O-ends of the chain were found in the region between 4.25 and 3.51 ppm in all the synthesised complexes. These signals were detected somewhat downfield than expected due to the deshielding effect of the electronegative atoms. Furthermore, the signals due to the proton of the −OH group in both the parent complex and adducts were found in the region between 5.35 and 4.85 ppm [23]. The protons of the bipyridine and the phenanthroline groups appeared in the aromatic region around 8.93–7.25 and 9.57–7.20 ppm, respectively [27,38]. The observed chemical shift with higher frequency in the adduct, bearing the phenanthroline moiety, could be ascribed to the higher number of aromatic rings compared to those of bipyridine.

The 13C NMR spectra of the complexes showed a significant peak due to the quaternary carbons [18] of NCS2 at 206.2, 204.2 and 204.5 ppm for complexes (1), (2) and (3), respectively. The upfield shift in the carbon signal of the adducts in comparison to the parent complex (1) has been attributed to the delocalisation of electron density in the NCS2Zn moiety and the electron cloud withdrawing resonance effect of the rings in the bipyridine and phenanthroline moiety upon coordination to the zinc atom [27,38,39]. The presence of this signal could also suggest the complexation between the metal atom and the dithiocarbamate ligand [38]. The aromatic carbon from the N-donor ligands of bipyridine and phenanthroline was found to resonate in the frequency range of 163.5–128.9 and 159.8–127.3 ppm, respectively [40]. The observed chemical shift of the aromatic carbon peaks in the bipyridine adducts towards a low field region could be attributed to the higher electron-donating tendency of the nitrogen atoms of bipyridine compared to those of the phenanthroline due to the extra ring in the phenanthroline molecule. The signal of the α-carbon in the ethyl moiety bearing the −OH group, of both the parent and the adducts, was observed around 60.3–31.2 ppm, while the β-carbon appeared in the range 66.1–53.7 ppm. These were in agreement with previous reports on similar ligands [41]. The lower signal in the α-carbon compared to the β-carbon could be ascribed to the deshielding effect due to the more electronegative oxygen on the β-carbon compared to the nitrogen atom on the α-carbon [41]. Furthermore, the carbon of the methyl group attached to the N-atom in the dithiocarbamate backbone in both the parent and adducts resonated at 44.9 ppm and around 26.0 ppm, respectively. In the adducts, the upfield movement of the C atoms of the dithiocarbamate backbones, N–CH3 and N–CH2CH2OH, could be attributed to the electron cloud withdrawing resonance effect of the phenyl groups in N-donor ligands attached to the metal centre [27].

3.3 FTIR spectroscopic studies of the complexes

The important bands in the infrared spectra of the prepared dithiocarbamate complexes were found in three regions: 1,060–940 cm−1 v(C–S), 1,580–1,450 cm−1 v(C═N) and 455–250 cm−1 v(M–S) [8]. In the parent complex (1), the thioureide ν(C═N) band occurred at 1,492 cm−1. However, a shift to lower wavelength was observed in the adducts at 1,475 and 1,481 cm−1 for complexes (2) and (3), respectively. The lowering of the vibrational frequency of the thioureide bands in the adducts compared to the parent complex has been ascribed to the increase in coordination number from four to six, which occurred upon adduct formation [42]. Hence, the change in geometry affected the degree of interaction that occurred between the dithiocarbamate ligand and the metal ion [42]. Furthermore, the presence of a single unsplit band in the parent complex and the adduct complexes, in the region between 977–981 cm−1, assigned to the C–S group, suggested the formation of a bidentate mode of bonding between the dithiocarbamate ligand and the central metal ion [43]. The bands due to the ν(–C–H) of the alkyl groups were observed in the region of 2,918–2,971 cm−1 [23]. The O–H stretching and bending vibrations were observed in the region of 3,287–3,377 and 1,580–1,619 cm−1, respectively, in all the complexes. The peak corresponding to M–S stretching vibration was found in the range 497–506 cm−1 [23].

3.4 X-ray diffraction analysis of the nanoparticles

The as-prepared ZnS nanoparticles were characterised by powder X-ray diffraction, and the patterns obtained are presented in Figure 3. In all the samples, diffraction patterns observed correspond to the (1 1 1), (2 2 0) and (3 1 1) planes of cubic (sphalerite) phase of ZnS nanoparticles, which agrees with the standard JCPDS ID: 00-005-0566. The sphalerite phase is well-known to be the more thermodynamically stable form of ZnS at room temperature [9] The observed XRD peaks in each of the nanoparticles were found to be relatively broad, indicating the nano-sized nature of the samples. Other unidentified peaks in the XRD pattern may be due to the compound used as the capping agent.

Figure 3 XRD pattern ZnS1, ZnS2 and ZnS3 nanoparticles obtained from (1), (2) and (3), respectively, as precursor complexes.
Figure 3

XRD pattern ZnS1, ZnS2 and ZnS3 nanoparticles obtained from (1), (2) and (3), respectively, as precursor complexes.

3.5 Transmission electron microscopy (TEM) studies

The TEM micrographs showing the morphologies and sizes of the ZnS nanoparticles are shown in Figure 4(a)–(c) along with their particle size distribution histogram, which was estimated using ImageJ software. The nanoparticles obtained from the parent complex (1), showed rice-shaped morphology, with a mean size of 2.63 nm. The morphology of the nanoparticles obtained from complex (2), represented as ZnS2, showed spherical morphology with a mean size of 5.27 nm. The nanoparticles obtained from complex (3) showed similar spherical morphology with a relatively larger particle mean size (6.52 nm) compared to ZnS1 and ZnS2. These observed differences in nanoparticles’ shape and size have been attributed to the change in the decomposition profile due to the introduction of a Lewis base into the structure of the precursor compounds, thereby altering the functional groups in the compound [25].

Figure 4 TEM micrographs of (a) ZnS1, (b) ZnS2 and (c) ZnS3, with their respective particle size distribution histogram.
Figure 4

TEM micrographs of (a) ZnS1, (b) ZnS2 and (c) ZnS3, with their respective particle size distribution histogram.

3.6 Ultraviolet-visible spectroscopic study

The photo-absorption properties of the synthesised ZnS nanoparticles were studied using UV-vis spectroscopy, and the obtained spectra are presented in Figures 5a–c. All the synthesised nanoparticles showed the photo-absorption property in the UV light region around 220–420 nm range. The spectra exhibited properties that were indicative of light absorption due to the band-gap transition [44]. The optical bandgap of the nanoparticles was calculated according to Tauc’s relation (equation (1)) [44,45], and the plots are presented as insets in the UV-spectra of Figure 5a–c.

(1) α h v = A ( h v − E g ) n ,

where A is a constant, α is the absorption coefficient, hv is the photon energy, E g is the optical bandgap and n = ½ (indirect transition) or n = 2 (in indirect transition). The bandgap can be obtained by extrapolating the linear portion of the plot (αE)2 vs E to α = 0. The optical parameters obtained from the absorption spectra are presented in Table 4. The bandgap values of all the ZnS nanoparticles from different precursor compounds showed higher bandgap energy than the bulk value (3.68 eV) [44]. This blue shift has been ascribed to the quantum confinement effect and is dependent on both the size and morphologies of the synthesised nanoparticles [44].

Figure 5 Absorption spectra of (a) ZnS1, (b) ZnS2 and (c) ZnS3, and their respective Tauc plots (inset).
Figure 5

Absorption spectra of (a) ZnS1, (b) ZnS2 and (c) ZnS3, and their respective Tauc plots (inset).

Table 4

Summary of optical spectra data from the UV-vis spectra

Nanoparticles Bandgap (eV) Band edge (nm) Size (nm) Absorption peak (nm)
ZnS1 4.34 286 2.42 275
ZnS2 4.09 303 2.88 289
ZnS3 4.08 304 2.92 289

The introduction of the Lewis bases into the parent compound showed a significant effect on the optical properties of the nanoparticles obtained. Table 4 presents the sizes and bandgap energies of the nanoparticles. An increase in the size of the nanoparticles was observed upon the introduction of the Lewis base, which seemed to also increase with an increase in the number of rings in the Lewis bases. This affected the bandgap energy, which showed a reduction since there is an inverse proportionality between the size of nanoparticles and bandgap.

3.7 Photoluminescence spectra

The Photoluminescence spectra of the synthesised ZnS nanoparticles, at an excitation wavelength of 250 nm, are shown in Figure 6. The emission peaks were found in the range 336–340 nm. These emission wavelengths contributed to near band edge emission and may originate from the recombination of the free excitons of ZnS within the nanosize regime [46]. In all the spectra, band energy of about 4.9 eV was observed which resulted in a blue shift when compared to the bandgap energy of bulk ZnS (3.68 eV). The broad nature of the spectra may be due to the large particle size distribution, as observed in the TEM micrographs. A weak emission peak was observed in the spectra of ZnS3 around 490 nm. This emission peak has been ascribed to the defect states or interstitial impurities, which are possibly present at the surface of the ZnS nanoparticles [47,48]. Generally, the fluorescence mechanism proceeds by the absorption of the photon which has comparable energy with the bandgap energy of the semiconductor material, imitating an electron–hole pair as shown in Figure 7 [49]. This energy becomes thermalised within a short time, such that the energy separation between the hole and electron becomes approximately equal to the energy of the gap, leading to the radiative recombination of the electron–hole pair, which consequently gives rise to the emission of photons (luminescence). Therefore, the bang gap energies of the nanomaterial are a rough reflection of the peak positions [49].

Figure 6 Photoluminescence spectra of ZnS nanoparticles.
Figure 6

Photoluminescence spectra of ZnS nanoparticles.

Figure 7 Photoluminescence mechanism in semiconductors material [50].
Figure 7

Photoluminescence mechanism in semiconductors material [50].

4 Conclusion

ZnS nanoparticles were successfully prepared from the thermolysis of Zn(ii) bis(N-methyl-N-ethanol dithiocarbamate) and its 2,2′-bipyridyl and 1,10′-phenanthroline adducts. The Zn(ii) complex and its respective adducts contained Zn atom coordinated to the dithiocarbamate group in an S,S′-bidentate fashion. The as-prepared ZnS nanoparticles gave spherical-shaped morphology with cubic sphalerite phase, which showed size increment with an increase in the bulkiness of the precursor complexes. The optical property of the nanoparticles showed a blue shift relative to the bandgap energy of bulk ZnS (3.68 eV).

Supplementary data

CCDC 1872719 and 1872720 for complex (1) and (2) respectively contains the supplementary crystallographic data for this dissertation. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.

Acknowledgements

Authors acknowledge Dr. Innocent Shuro of the Laboratory for Electron Microscopy (LEM) for the morphological studies of the nanoparticles using transition electron microscopy (TEM).

  1. Funding information: Financial support from the National Research Foundation and the North-West University, South Africa, are greatly appreciated.

  2. Author contributions: D.C.O. – conceptualisation, investigation, writing – review and editing; J.O.A. – formal analysis, writing – review and editing; R.T.P. – methodology, investigation; F.F.B. – methodology, investigation, E.H. – software.

  3. Conflict of interest: The authors declare no conflict of interest.

  4. Ethical approval: The conducted research is not related to either human or animal use

  5. Data availability statement: Data sharing is not applicable to this article as no datasets were generated or analysed during the current study.

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Received: 2021-06-14
Revised: 2021-09-24
Accepted: 2021-09-27
Published Online: 2021-11-20

© 2021 Damian C. Onwudiwe et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/chem-2021-0094
Keywords for this article
dithiocarbamate; ZnS nanoparticles; crystal structure; optical properties
Creative Commons
BY 4.0

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