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Two new zinc(ii) coordination complexes constructed by phenanthroline derivate: Synthesis and structure

  • Jingdong Feng , Beihao Su , Xinxin Yi , Zhiguo Kong EMAIL logo and Limin Chang EMAIL logo
Published/Copyright: April 17, 2023
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Main Group Metal Chemistry
From the journal Main Group Metal Chemistry Volume 46 Issue 1

Abstract

Two new Zn(ii) coordination complexes [Zn(L)(dna)(H2O)] (1) and [Zn(L)(glu)]2·H2O (2) (L = 2-(4-fluorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline, H2dna = 3,5-dinitrosalicylic acid, H2glu = glutaric acid) have been hydrothermally synthesized and characterized by single crystal X-ray diffraction, elemental analysis, fluorescence spectrum, and infrared spectroscopy. For complex 1, the dna2− anion adopts μ 1 -η 1 :η 1 chelating bidentate mode to coordinate with one Zn(ii) atom and π–π stacking interactions are formed between the L ligands. For complex 2, glu2− anions connect Zn(ii) atoms to form a wavy two-dimensional layer, and the L ligands are attached on two sides of the two-dimensional layer.

Keywords: coordination complex; Zn(ii); glutaric2− acid; 3,5-dinitrosalicylic acid

1 Introduction

As an emerging class of unique and interesting organo-inorganic hybrid crystalline materials, coordination complexes built of metal ions/clusters (Song et al., 2021; Yang et al., 2010) and bridging organic ligands have got a lot of attention in the past several decades (Chen, 2016; Wei et al., 2008). It is an infinite extension driven by self-assembly into one-dimension (Wang et al., 2017), two-dimension (Zhu et al., 2008), or three-dimension (Aghabozorg et al., 2011; Mirzaeib et al., 2014). In the process, many different factors can affect the architecture of the coordination complexes (Chen et al., 2021a; Zhang et al., 2020). Among these factors, the selection of excellent carboxylate ligands (Wang et al., 2014, 2021) and nitrogen-containing ancillary ligands (Bhargao et al., 2020; Li et al., 2022) make a number of significant contributions to obtain desired structures and properties (Bazargana et al., 2019; Chen et al., 2021b). Carboxylic acid ligands could be divided into two types, namely rigid aromatic ligands or heterocyclic acids (Zhang et al., 2015) and flexible aliphatic ligands (Wang et al., 2009). The flexible aliphatic ligands due to their aliphatic chain can provide multiple possibilities for the construction of frameworks (Liu et al., 2021). For example, glutaric acid (H2glu) as a flexible ligand can exhibit diverse coordination modes and topologies by means of its two carboxylate groups. Dutta et al. (2019) reported [Zn(glu)(4-nvp)] (4-nvp = 4-(1-naphthylvinyl)pyridine) with glutaric acids, and the results interestingly showed that two Zn(ii) centers are equivalently bridged by four μ 2 , η 2 -carboxylate groups from four different glutaric acids. In addition, compared with flexible aliphatic ligands, rigid aromatic ligands are usually used to control and stable the framework. For example, 3,5-dinitrosalicylic acid as an asymmetric bridging ligand can form a six-membered ring through the coordination of the carboxylate groups and hydroxyl groups with metal ions, which can increase the stabilization of the solid networks. Tian et al. (2020) synthesized a new coordination polymer, [{Bu2Sn(3,5-(NO2)2-2-OC6H2COO)}2(4,4′-bpy)] n and 3,5-dinitrosalicylate as doubly charged anion ligand to coordinate to tin atoms. In addition to the ligands, the choice of metal ions is also very important. Compared with rare earth metals, transition metals are cheaper and easier to obtain; therefore, it can replace expensive rare earth metals to build coordination polymers. Not only that, but it is of great significance in the field of photoluminescence. Zinc metal ions have a variety of coordination modes, which can increase the structural stability of zinc coordination polymer after binding with organic ligands (Chen et al., 2016; Wang et al., 2020). Taking the advantage of above interesting properties, we have synthesized and characterized two zinc(ii) coordination complexes with glutaric acid and 3,5-dinitrosalicylic acid.

In this article, we adopt hydrothermal methods to carry out our experiment and report two coordination complexes with zinc(ii): [Zn(L)(dna)(H2O)] (1) and[Zn(L)(glu)]2·H2O (2) (L = 2-(4-fluorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline, H2dna = 3,5-dinitrosalicylic acid, and H2glu = glutaric acid).

2 Results and discussion

2.1 Structural analysis

As shown in Figure 1, 1 consists of an independent Zn(ii) atom, one organic L ligand, one dna2− anion, and one coordinated water. Each Zn(ii) atom is five-coordinated by two nitrogen atoms (N(1) and N(2)) from one L ligand, three oxygen atoms (O(1W), O(2), and O(3)) from one water molecule and one dna2− anion in a twisted square-pyramidal configuration. The atoms N(1), N(2), O(2), and O(3) constitute the basal plane of the square pyramid, while O(1W) is located at the top position. The dna2− anion chelates one Zn(ii) atom in a μ 1 -η 1 :η 1 bidentate mode. The adjacent [Zn(L)(dna)(H2O)] molecules are formed into a bimolecular structure through π–π interactions [Cg4⋯Cg4iv, centroid-to-centroid distance of 3.4634(14) Å, dihedral angle of 0.03(11)°, Table 1] (Figure 2). Interestingly, there exists another π–π interaction in 1. The L ligands furnish π–π stacking interactions between the parallel L ligands (dihedral angle of 0.00(13)°) of adjacent bimolecular structures [Cg3⋯Cg3iii, centroid-to-centroid distance of 3.5625(15) Å, slippage distance of 1.401 Å, Table 1], making up a one-dimensional supramolecular chain (Figure 3).

Figure 1 Coordination environment of the Zn(ii) ion of 1.
Figure 1

Coordination environment of the Zn(ii) ion of 1.

Table 1

π–π Interactions for (Å, °) 1

Ring (I)⋯Ring (J) Centroid to centroid distance (Å) α (°) Slippage distance (Å) Symmetry code#
Cg3⋯Cg3iii 3.5625(15) 0.00(13) 1.401 1 − x, −y, 1 − z
Cg4⋯Cg4iv 3.4634(14) 0.03(11) 1.032 −x, −y, 1 − z

Ring codes – Cg3: N(2)/C(6)-C(10), Cg4: C(4)-C(6)/C(10)-C(12). α is the dihedral angle between planes I and J.

Figure 2 View of the bimolecular structure of 1.
Figure 2

View of the bimolecular structure of 1.

Figure 3 View of the 1D supramolecular chain of 1.
Figure 3

View of the 1D supramolecular chain of 1.

As seen in Figure 4, there exist the N–H⋯O hydrogen bonds (N(3)–H(3A)⋯O(1)ii, Table 4), which further make the adjacent chains expand to a three-dimensional supramolecular layer (Figure 5). Additionally, O–H⋯O and O–H⋯N hydrogen bonds (O(1W)–H(1A)⋯O(2), O(1W)–H(1A)⋯O(3), O(1W)–H(1B)⋯N(2), and O(1W)–H(1B)⋯N(4)iii, Table 2) further make the stability of the three-dimensional supramolecular structure.

Figure 4 View of the hydrogen bonds between dnsa2− anions and L ligands.
Figure 4

View of the hydrogen bonds between dnsa2− anions and L ligands.

Figure 5 View of the 3D supramolecular structure of 1.
Figure 5

View of the 3D supramolecular structure of 1.

Table 2

H-Bonding geometry parameters (Å, °) for complexes 1 and 2

Complex D–H⋯A D–H (Å) H⋯A (Å) D⋯A (Å) D–H⋯A (°) Symmetry code#
1 N(3)–H(3A)⋯O(1)ii 0.86 1.85 2.693(3) 165.8 −x, −1/2 + y, ½ − z
O(1W)–H(1A)⋯O(2) 0.85 2.48 3.042(3) 124.1
O(1W)–H(1A)⋯O(3) 0.85 2.65 3.189(3) 122.9
O(1W)–H(1B)⋯N(2) 0.85 2.57 3.150(3) 126.7
O(1W)–H(1B)⋯N(4)iii 0.85 2.08 2.710(3) 130.1 1 − x, −y, 1 − z
2 N(4)–H(4)⋯O(1)iii 0.86 1.99 2.823(14) 164 3 − x, y, 4 − z
N(8)–H(8A)⋯O(3)iii 0.86 2.07 2.877(14) 157 3 − x, y, 4 − z
O(1W)–H(1A)⋯O(4)iv 0.85 2.07 2.896(19) 166 −1/2 + x, 1/2 + y, z
O(1W)–H(1B)⋯O(8)v 0.85 2.19 3.024(19) 167 −1/2 + x, 1/2 + y, − 1 + z

As can be observed in Figure 6, the asymmetric unit of 2 contains two Zn(ii) atoms, two chelating L ligands, two glu2− anions, and one free water molecule. Each Zn(ii) atom bonds to three carboxylate oxygen atoms from three different glu2− anions and two nitrogen atoms from one chelating L ligand in a distorted tetragonal pyramid geometry. As seen in Figure 7, two Zn(ii) centers are connected by carboxylate groups from one glu2− anion with μ 2 -η 1 :η 1 coordination manners, generating a binuclear Zn2 unit with a Zn⋯Zn distance of 10.628 Å. Further linkage of these Zn2 units by the other μ 4 -glu2− anions forms a wavy two-dimensional layer with equatorial plane symmetry along the c-axis.

Figure 6 Coordination environment of the Zn(ii) ion of 2 (symmetry codes: (i) x, y, 1 + z; (ii)7/2 − x, 1/2 + y, 5 − z).
Figure 6

Coordination environment of the Zn(ii) ion of 2 (symmetry codes: (i) x, y, 1 + z; (ii)7/2 − x, 1/2 + y, 5 − z).

Figure 7 View of the 2D layer structure of 2 constructed by the glu2− anions.
Figure 7

View of the 2D layer structure of 2 constructed by the glu2− anions.

As illustrated in Figure 8, the conjugated L ligands are attached on two sides of the layer. As shown in Figure 9, there exist the N–H⋯O hydrogen bonds (N(4)–H(4)⋯O(1)iii, N(8)–H(8A)⋯O(3)iii, Table 2), which further make the adjacent two-dimensional layers to grow into a three-dimensional supramolecular structure (Figure 10). Additionally, O–H⋯O hydrogen bonds (O(1W)–H(1A)⋯O(4)iv, O(1W)–H(1B)⋯O(8)v, Table 2) further consolidates the three-dimensional supramolecular structure.

Figure 8 View of the 2D layer structure of 2 constructed by the glu2− anions and L ligands.
Figure 8

View of the 2D layer structure of 2 constructed by the glu2− anions and L ligands.

Figure 9 View of the N–H⋯O hydrogen bonds between glu2− anions and L ligands.
Figure 9

View of the N–H⋯O hydrogen bonds between glu2− anions and L ligands.

Figure 10 View of the 3D supramolecular structure of 2.
Figure 10

View of the 3D supramolecular structure of 2.

2.2 IR spectroscopy

The IR spectroscopy curve of 2 was shown in the region of 4,000–400 cm−1 (Figure 11). The broad band at 3,428 cm−1 may be assigned to the vibrations of water molecules of 2. The two peaks at 1,608 and 1,312 cm−1 correspond to the asymmetric and symmetric vibrations of carboxylate groups of the glu2− anions. Peaks at 1,405 and 1,074 cm−1 were observed, which is characteristic of the C–N and C═N stretching vibrations of L ligand stretching frequency of the L ligand.

Figure 11 IR spectroscopy curve of 2.
Figure 11

IR spectroscopy curve of 2.

2.3 Luminescent properties

The luminescent properties of the free organic ligands and 2 have been studied in the solid state at room temperature (Figure 12). The free L ligand and H2glu show emission bands centered at 557 nm (λ ex = 325 nm) and 536 nm (λ ex = 325 nm), respectively, which can be attributed to the π*–n or π*–π transition. The emission peak of Zn(ii)-containing 2 occurs at 575 nm (λ ex = 325 nm). Compared with the free L ligand, the emission peak of 2 is red-shifted by 18 nm. Due to the configuration of d10, Zn(ii) ions are difficult to oxidize or reduce (Yam and Wong, 2011). Therefore, the emission of 2 is neither metal-to-ligand charge transfer (MLCT) nor ligand-to-metal charge transfer (LMCT) (Guo et al., 2009). The emission of 2 could be owing to the intraligand transitions.

Figure 12 Room-temperature solid-state photoluminescence spectra of 2, L ligand, and H2glu.
Figure 12

Room-temperature solid-state photoluminescence spectra of 2, L ligand, and H2glu.

3 Conclusions

In summary, two new Zn(ii) coordination complexes were obtained and their structures were characterized. In 1, the L ligands furnish π–π stacking interactions between the L ligands of adjacent bimolecular structures, generating a one-dimensional supramolecular chain. The adjacent 1D chains were extended 3D supramolecular structures through the hydrogen bonds. In 2, the adjacent Zn2 units are linked together via the other glu2− anions to yield a wavy two-dimensional layer. Moreover, the 2D layers are further packed into a 3D supramolecular framework through hydrogen bond interactions.

Experimental

All chemicals for syntheses were used as received from commercial sources (Shanghai Hengfei Biological Technology Co., Ltd and Henan Pusai Chemical Products Co., Ltd, China). Elemental analysis (C, H, N) was carried out using a Perkin-Elmer 240 CHN elemental analyzer (Perkin-Elmer, North Waltham, USA). IR spectrum was recorded on an Alpha Centaurt FT/IR Spectrophotometer (Mattson Technology, USA). The emission spectra were measured on a Renishaw inVia Raman Microscope (Renishaw inVia, UK).

Preparation of [Zn(L)(dna)(H2O)] (1)

Zn(SO4)·7H2O (0.15 mmol, 0.043 g), L (0.15 mmol, 0.047 g), 3,5-dinitrosalicylic acid (0.3 mmol, 0.068 g), and anhydrous ethanol (1.5 mL) were mixed and dissolved in deionized water (10 mL). NaOH (0.6 mmol, 0.024 g) was added, and then, the reaction mixture was sealed in a 20 mL stainless steel vessel and heated at 453 K for 96 h. Yellow block crystals of 1 were obtained with a yield of 0.052 g (ca. 56%, based on the L). Anal. (%) calculated for C26H15FN6O8Zn: C, 50.06%; H, 2.42%; N, 13.47%. Found: C, 49.54%; H, 2.39%; N, 13.36%.

Preparation of [Zn(L)(glu)]2·H2O (2)

Zn(CH3COO)2 (0.3 mmol, 0.055 g), L (0.3 mmol, 0.094 g) and H2glu (0.3 mmol, 0.040 g) were mixed and dissolved in deionized water (12 mL), which was then adjusted to the pH value to 7.45 by addition of 1 mol‧L−1 NaOH solution. The mixture was sealed in a 20 mL stainless steel vessel and heated at 448 K for 96 h. Yellow block crystals of 2 were obtained with a yield of 0.079 g (ca. 51%, based on the Zn). Anal. (%) calculated for C48H36F2N8O9Zn2: C, 55.56%; H, 3.50%; N, 10.80%. Found: C, 55.13%; H, 3.46%; N, 10.71%.

X-ray crystallography

X-ray diffraction data of 1 and 2 were collected at 296(2)K on a Rigaku RAXIS-RAPID diffractometer, with graphite-monochromatized Mo-Kα radiation (λ = 0.71073 Å) using the ω scan technique. The structures were resolved using SIR2014 (Burla et al., 2015) and refined using the SHELXL2018/3 program (Sheldrick, 2015). The models were refined on F 2 by a full-matrix least-squares technique. Non-hydrogen atoms were refined with anisotropic displacement parameters. The hydrogen atoms of the organic ligands were placed in ideal positions and refined as riding atoms. Detailed information about the crystal data for 1 and 2 was summarized in Table 3. Detailed information about the selected bond lengths and bond angles were given in Table 4. Full details of the X-ray structure determination of coordination complexes 1 and 2 have been deposited with the Cambridge Crystallographic Data Center, and the CCDC 2182024 and 2209851 represent 1 and 2.

Table 3

Crystalline data and refinement parameters for complexes 1 and 2

Complex 1 2
Empirical formula C26H15FN6O8Zn C48H36F2N8O9Zn2
Formula weight 623.81 1,037.59
Crystal system Monoclinic Monoclinic
Space group P21/c C2
a (Å) 7.6464(6) 32.578(7)
b (Å) 20.4215(17) 9.852(2)
c (Å) 15.5760(13) 14.084(3)
α (°) 90 90
β (°) 98.887(2) 106.07(3)
γ (°) 90 90
Volume (Å3) 2,403.0(3) 4,343.6(16)
Z 4 4
D c (g·cm−3) 1.724 1.587
µ (mm−1) 1.098 1.183
F(000) 1,264 2,120
θ range (°) 1.657–26.068 3.010–25.007
Crystal size (mm) 0.749 × 0.174 × 0.144 0.203 × 0.187 × 0.122
Tot. reflections 4,755 6,739
Uniq. reflections, R int 13,110, 0.0322 17,001, 0.0756
GOF on F 2 1.029 1.014
R 1 indices [I > 2σ(I)] 0.0382 0.0576
wR 2 indices (all data) 0.1027 0.1449
∆ρ min, ∆ρ max (e·Å−3) −0.534, 0.514 −0.516, 0.725
CCDC No. 2209851 2182024
Table 4

Selected bond lengths (Å) and angles (°) for the complexes 1 and 2

Complex 1
Bond Dist. Bond Dist.
Zn(1)–N(1) 2.116(2) Zn(1)–O(3) 1.9810(19)
Zn(1)–N(2) 2.13(2) Zn(1)–O(1W) 2.052(2)
Zn(1)–O(2) 1.9632(18)
Angle (°) Angle (°)
O(2)–Zn(1)–O(3) 91.73(8) O(3)–Zn(1)–N(1) 152.42(9)
O(2)–Zn(1)–O(1W) 98.49(9) O(3)–Zn(1)–N(2) 85.84(8)
O(3)–Zn(1)–O(1W) 104.51(9) N(2)–Zn(1)–N(1) 77.80(8)
O(2)–Zn(1)–N(1) 97.52(8) O(1W)–Zn(1)–N(1) 99.76(9)
O(2)–Zn(1)–N(2) 163.14(9) O(1W)–Zn(1)–N(2) 98.27(8)
Complex 2
Bond Dist. Bond Dist.
Zn(1)–N(1) 2.113(9) Zn(1)–O(5) 2.095(8)
Zn(1)–N(2) 2.156(11) Zn(2)–O(4)ⅰ 1.951(7)
Zn(2)–N(5) 2.099(8) Zn(2)–O(6) 2.006(7)
Zn(2)–N(6) 2.164(10) Zn(2)–O(7)ii 2.097(8)
Zn(1)–O(2) 1.941(7) Zn(1)–O(8)ii 2.014(7)
Angle (°) Angle (°)
O(2)–Zn(1)–O(5) 99.2(3) O(5)–Zn(2)–N(4)ⅰ 125.0(3)
O(2)–Zn(1)–N(1) 111.2(3) O(6)–Zn(2)–N(4)ⅰ 104.0(4)
O(2)–Zn(1)–N(2) 106.9(4) N(5)–Zn(2)–O(7)ii 87.4(3)
O(5)–Zn(1)–N(1) 87.8(3) N(6)–Zn(2)–O(7)ii 157.7(3)
O(5)–Zn(1)–N(2) 153.3(3) O(6)–Zn(2)–O(7)ii 92.1(3)
N(1)–Zn(1)–N(2) 77.7(4) O(7)ii–Zn(2)–O(4)ⅰ 98.1(3)
O(6)–Zn(2)–N(5) 138.1(3) N(1)–Zn(1)–O(8)ii 150.6(3)
O(6)–Zn(2)–N(6) 88.7(3) N(2)–Zn(1)–O(8)ii 90.0(3)
O(6)–Zn(2)–O(4)ⅰ 96.5(3) O(2)–Zn(1)–O(8)ii 97.8(3)
N(5)–Zn(2)–N(6) 77.3(4) O(5)–Zn(1)–O(8)ii 92.0(3)

Symmetry codes: i x, y, 1 + z; ii 7/2 − x, 1/2 + y, 5 − z.

  1. Funding information: This research was supported by the Natural Science Foundation of China (No. 52072145) and the Scientific and Technological Developing Scheme of Siping (No. 2016048).

  2. Author contributions: Jingdong Feng: writing – original draft, methodology, experimental work; Beihao Su: writing – original draft, writing – review and editing; Xinxin Yi: experimental work; Zhiguo Kong: writing – review and editing, visualization, software; Limin Chang: data curation, validation.

  3. Conflict of interest: The authors declare no competing financial interest with any financial organization regarding the material discussed in the manuscript.

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Received: 2022-09-28
Revised: 2023-03-30
Accepted: 2023-03-02
Published Online: 2023-04-17

© 2023 the author(s), 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/mgmc-2022-8042
Keywords for this article
coordination complex; Zn(ii); glutaric2− acid; 3,5-dinitrosalicylic acid
Creative Commons
BY 4.0

Articles in the same Issue

  1. Research Articles
  2. Two new zinc(ii) coordination complexes constructed by phenanthroline derivate: Synthesis and structure
  3. Lithium fluoroarylsilylamides and their structural features
  4. On computation of neighbourhood degree sum-based topological indices for zinc-based metal–organic frameworks
  5. Two novel lead(ii) coordination complexes incorporating phenanthroline derivate: Synthesis and characterization
  6. Thermodynamics of transamination reactions with aminotrimethylsilanes and diaminodimethylsilanes
  7. From synthesis to biological impact of palladium bis(benzimidazol-2-ylidene) complexes: Preparation, characterization, and antimicrobial and scavenging activity
  8. Novel ruthenium(ii) N-heterocyclic carbene complexes: Synthesis, characterization, and evaluation of their biological activities
  9. Entropy measures of the metal–organic network via topological descriptors
  10. Rapid Communication
  11. Synthesis and crystal structure of an ionic phenyltin(iv) complex of N-salicylidene-valine
  12. Special Issue: Theoretical and computational aspects of graph-theoretic methods in modern-day chemistry (Guest Editors: Muhammad Imran and Muhammad Javaid)
  13. Topological indices for random spider trees
  14. On distance-based indices of regular dendrimers using automorphism group action
  15. Retraction
  16. Retraction to “Aluminium(iii), Fe(ii) Complexes and Dyeing Properties of Apigenin(5,7,4′-trihydroxy flavone)”
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