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Two new Zn(ii) coordination polymers incorporating 2-(2,6-dichlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline: Synthesis and structure

  • Huilin Wang , Xin Wang , Meimiao Li and Jingdong Feng EMAIL logo
Published/Copyright: May 20, 2024
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Main Group Metal Chemistry
From the journal Main Group Metal Chemistry Volume 47 Issue 1

Abstract

Based on phenanthroline derivate ligand and Zn(ii), two novel coordination polymers, namely [Zn(L)(hta)] n (1) and {[Zn2(L)2(dhb)2]·H2O} n (2) (L = 2-(2,6-dichlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline, H2hta = heptanedioic acid, and H2dhb = 3,5-dinitro-2-hydroxybenzoic acid), have been synthesized under the hydrothermal condition. For 1, each hta anion bridges two Zn(ii) atoms in a tridentate mode to shape into a chain structure and through different π–π stacking interactions to form a three-dimensional supramolecular structure. The L ligand of 2 connects two neighbouring Zn(ii) atoms to give a 1D chain, which is further extended into the 2D supramolecular layer.

Keywords: coordination polymer; Zn(ii); phenanthroline derivatives

1 Introduction

As a special kind of coordination solids, coordination polymers (CPs) developed rapidly for the past decades [1,2,3,4]. CPs have been at the forefront of study in materials science due to CPs with complex architectures and with wide applications [5,6,7], such as supercapacitors [8], degradation [9,10], catalysis [11,12], fluorescence [13], and proton conduction [14,15]. It is a crucial step for the self-assembly process of CPs to select suitable organic bridging ligands [16,17,18]. It is generally known that N-donor ligands are excellent ligands for the synthesis of CPs because of their excellent binding abilities [19]. For example, phenanthroline derivate ligands can provide multiple ligand patterns and a large number of ligand sites, resulting in CPs with exciting structures [20,21,22,23]. In addition, metal centres with d0 and d10 structures also confer special properties on CPs. For example, metal (Zn, Cd) ions with d10 configuration are particularly promising due to their applications in luminescence and biological activities [24,25].

Based on this, we used the hydrothermal method to synthesize two new CPs with Zn(ii) and phenanthroline derivate ligand (L = 2-(2,6-dichlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline).

2 Results and discussion

2.1 Structural analysis

CP 1 crystallizes in the monoclinic system, P21/c space group with a Zn(ii) atom, an L ligand, and a hta anion. In Figure 1, each Zn(ii) atom is coordinated by three oxygen atoms (O(2), O(3i), O(4i)) from two different hta anions and two nitrogen atoms (N(1) and N(2)) from one L ligand. The atoms N(1), N(2), O(3i), and O(4i) make up the basal plane of the square pyramid, while the top position is occupied by O(2). Each hta anion bridges two Zn(ii) atoms in a tridentate mode to shape into a chain structure with a Zn∙∙∙Zn distance of 10.180 Å (Figure 2). The L ligands are located on two sides of the chain. As shown in Figure 3, there exits two π–π interactions in adjacent chains [Cg6∙∙∙Cg6iv and Cg5∙∙∙Cg8vi, Table 1] and N–H∙∙∙O hydrogen bonds [N(4)–H(4)∙∙∙O(1)ⅳ, Table 2]. The neighboring chains grow up to a 2D supramolecular layer through π–π interactions [Cg6∙∙∙Cg6iv, centroid-to-centroid distance being 3.656(4) Å, dihedral angle of 0.0(3)°] (Figure 4). Moreover, the 2D supramolecular layers are formed into 3D architecture by another π–π interactions [Cg5∙∙∙Cg8vi, face-to-face distance of ca. 3.462(2) Å, slippage distance of 1.696 Å] (Figure 5).

Figure 1 Coordination environment of the Zn(ii) ion of 1 (symmetry codes: i−x + 2, y + 1/2, −z + 3/2).
Figure 1

Coordination environment of the Zn(ii) ion of 1 (symmetry codes: i−x + 2, y + 1/2, −z + 3/2).

Figure 2 View of the 1D chain structure of 1 constructed by hta anion.
Figure 2

View of the 1D chain structure of 1 constructed by hta anion.

Figure 3 View of the π–π interactions and N–H∙∙∙O hydrogen bonds of 1 between two 1D chains.
Figure 3

View of the π–π interactions and N–H∙∙∙O hydrogen bonds of 1 between two 1D chains.

Table 1

π–π interactions for (Å, °) 1 and 2

Complex Ring (I)⋯ring (J) Centroid tocentroid distance (Å) α (°) Slippage distance (Å) Symmetry code
1 Cg6⋯Cg6iv 3.656(4) 0.0(3) 1.426 −x + 1, −y + 1, −z + 1
2 Cg5⋯Cg8vi 3.748(4) 10.4(3) 1.696 −x + 1, y − 1/2, −z + 1/2
Cg5⋯Cg5iv 3.670(3) 0.0(2) 1.300 −x + 1/2, −y + 1/2, −z
Cg8⋯Cg8ii 3.596(3) 0.6(2) 0.331 −x + 1, y, −z + 1/2

Complex 1: Ring codes – Cg5: N(1)/C(1)–C(5), Cg6: N(2)/C(6)–C(10), Cg8: C(14)–C(19).

Complex 2: Ring codes – Cg5: N(2)/C(6)–C(10), Cg8: C(21)–C2(26). α is the dihedral angle between planes I and J.

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(4)–H(4)⋯O(1)ⅳ 0.86 1.93 2.732(7) 154.4 −x + 1, −y + 1, −z + 1
2 N(4)–H(4)⋯O(1)ⅳ 0.86 1.92 2.757(4) 163.3 −x + 1/2, −y + 1/2, −z
N(4)–H(4)⋯O(2)ⅳ 0.86 2.53 3.167(4) 131.1 −x + 1/2, −y + 1/2, −z
O(1W)–H(1A)⋯O(1) 0.85 1.99 2.837(4) 176.5
Figure 4 View of the 2D layer structure of 1.
Figure 4

View of the 2D layer structure of 1.

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

View of the 3D supramolecular structure of 1.

In addition, N–H∙∙∙O hydrogen bond (N(4)–H(4) = 0.86, H(4)∙∙∙O(1)iv = 1.93, N(4)∙∙∙O(1)iv = 2.732(7) Å, ∠ N(4)–H(4)∙∙∙O(1)iv = 154.4°, Table 2) further firms up the 3D supramolecular structure.

The asymmetric unit of 2 is composed of one Zn(ii) atom, an L ligand, a dhb anion, and a half-free water molecule. As shown in Figure 6, each Zn(ii) is coordinated by three nitrogen atoms from two different L ligands (N(1)–Zn(1) = 2.090(3), N(2)–Zn(1) = 2.130(3) and N(3)–Zn)–Zn(1)i = 2.073(3) Å) and two oxygen atoms from one bis-chelating dhb anion (O(2)–Zn(1) = 1.986(3) and O(3)–Zn(1)= 2.021(3) Å), in a twisted [ZnN3O2] square-pyramidal geometry (Table 1). The Zn–O (1.986(3) and 2.021(3) Å) and Zn–N (from 2.073(3) to 2.090(3) Å) distances are near to those reported observed in other analogous Zn(ii) CP [26]. The L ligand connecting two neighbouring Zn(ii) atoms to give a 1D chain along the c axis, as an uncommon µ 2-ligand in unprotonated phenanthroline derivatives, is displayed, and the Zn∙∙∙Zn distance is 8.015 Å (Figure 7).

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

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

Figure 7 View of the double chains of 2 formed by π–π interactions.
Figure 7

View of the double chains of 2 formed by π–π interactions.

The dhb anions are located at one side of the chain in a bidentate fashion by two oxygen atoms. The adjacent chains turn into a double chain structure through π–π interactions [Cg5⋯Cg5iv, centroid-to-centroid distance of 3.670(3) Å, dihedral angle being 0.0(2)°, Table 1] (Figure 7). Ulteriorly, the dhb anions of double chains render π–π stacking interactions between the approximately parallel dhb anions (dihedral angle of 0.6(2)°) of adjacent double chains [Cg8⋯Cg8ii, centroid-to-centroid distance of 3.596(3) Å, Table 1], making the double chains to a 2D supramolecular layer (Figure 8). In addition, N–H∙∙∙O and O–H∙∙∙O hydrogen bonds (N(4)–H(4)∙∙∙O(1)iv, N(4)–H(4)∙∙∙O(2)iv, and O(1W)–H(1A)∙∙∙O(1), Table 2) make further efforts to stabilize the 2D supramolecular layer.

Figure 8 View of the 2D supramolecular layer of 2.
Figure 8

View of the 2D supramolecular layer of 2.

3 Conclusions

In summary, two novel Zn(Ⅱ) CPs were synthesized and their structures were studied. CP 1 exhibits a 1D chain structure and the neighboring chains are connected through π–π interactions to generate a 2D supramolecular layer. The 2D supramolecular layers are joined together by another π–π interactions to yield 3D architecture, which stabilized the 3D by N–H∙∙∙O hydrogen bond. 2 shows 1D chain structure and further connected by π–π interactions interactions to form a double chain structure, which is extended into more stable 2D architecture.

Experimental

All chemicals and reagents were of commercial origin and obtained from Shanghai Hengfei Biological Technology Co., Ltd. and Henan Pusai Chemical Products Co., Ltd., China. Elemental analysis (C, H, N) was determined with a Perkin-Elmer 240 CHN elemental analyzer (Perkin-Elmer, North Waltham, USA).

Preparation of [Zn(L)(hta)] n (1)

The reagent Zn(CH3COO)2·2H2O (0.1 mmol, 0.0220 g), L (0.1 mmol, 0.0365 g), heptanedioic acid (0.1 mmol, 0.0161 g), C2H5OH (1 mL), and 9 mL H2O were mixed, which was adjusted to pH = 5.16 by the addition of KOH solution (0.2 mmol·L−1) and placed in 20 mL Teflon-lined autoclave. The mixture was sealed and heated at 398 K for 4 days and then cooled slowly to room temperature. Yellow block crystals of 1 were collected in a 39% yield based on Zn. Anal. Calcd for C26H20Cl2N4O4Zn, %: C, 53.04%; H, 3.42%; N, 9.52%. Found: C, 52.38%; H, 3.38%; N, 9.43%.

Preparation of {[Zn2(L)2(dhb)2]·H2O} n (2)

The reagent Zn(CH3COO)2·2H2O (0.2 mmol, 0.0439 g), L (0.2 mmol, 0.0730g), 3,5-dinitro-2-hydroxybenzoic acid (0.2 mmol, 0.0456 g), C2H5OH (1 mL), and 10 mL H2O were mixed, NaOH (0.2 mmol, 0.012 g) was added, which was measured to pH = 5.66, and then, the mixture was placed in 20 mL Teflon-lined autoclave, sealed and heated at 448 K for 4 days, and cooled slowly to room temperature. Yellow block crystals of 2 were collected in 51% yield based on Zn. Anal. Calcd for C52H26Cl4N12O15Zn2 (Tables 3 and 4).

Table 3

Crystalline data and refinement parameters for complexes 1 and 2

Complex 1 2
Empirical formula C26H20Cl2N4O4Zn C52H26Cl4N12O15Zn2
Formula weight 588.73 1,331.39
Crystal system Monoclinic Monoclinic
Space group P21/c C2/c
a (Å) 11.284(2) 24.268(2)
b (Å) 11.382(2) 14.5813(15)
c (Å) 18.517(4) 15.7042(16)
α (°) 90 90
β (°) 90.87(3) 94.148(2)
γ (°) 90 90
Volume (Å3) 2,377.9(8) 5,542.5(10)
Z 4 4
D c (g·cm−3) 1.644 1.596
µ (mm−1) 1.301 1.138
F(000) 1,200 2,680
θ range (°) 3.345–25.008 1.630–25.007
Crystal size (mm) 0.185 × 0.102 × 0.086 0.215 × 0.172 × 0.137
Tot. reflections 17,965 15,431
Uniq. reflections, R int 4,133, 0.1136 4,857, 0.0369
GOF on F 2 1.035 1.059
R 1 indices [I > 2σ(I)] 0.0635 0.0531
wR 2 indices (all data) 0.1724 0.1516
∆ρ min, ∆ρ max (e·Å−3) 0.483, −0.857 0.714, −0.917
CCDC No. 2304359 2304360
Table 4

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

Complex 1
Bond Dist. Bond Dist.
N(1)–Zn(1) 2.106(5) O(3)–Zn(1)ⅰ 1.994(5)
N(2)–Zn(1) 2.090(5) O(4)–Zn(1)ⅰ 2.405(7)
O(2)–Zn(1) 1.954(4)
Angle (°) Angle (°)
O(2)–Zn(1)–O(3)ii 112.0(2) N(2)–Zn(1)–N(1) 79.59(19)
O(2)–Zn(1)–N(2) 120.43(18) O(2)–Zn(1)–O(4)ii 111.4(2)
O(3)ii–Zn(1)–N)–N(2) 103.6(2) O(3)ii–Zn(1)–O(4)ii 57.7(2)
O(2)–Zn(1)–N(1) 101.30(19) N(2)–Zn(1)–O(4)ii 128.0(2)
O(3)ii–Zn(1)–N(1) 137.6(2) N(1)–Zn(1)–O(4)ii 86.66(18)
Complex 2
Bond Dist. Bond Dist.
N(1)–Zn(1) 2.090(3) O(2)–Zn(1) 1.986(3)
N(2)–Zn(1) 2.130(3) O(3)–Zn(1) 2.021(3)
N(3)–Zn(1)i 2.073(3)
Angle (°) Angle (°)
O(2)–Zn(1)–O(3) 87.88(12) N(3)ⅲ–Zn(1)–N(1) 116.37(13)
O(2)–Zn(1)–N(3)ⅲ 121.76(13) O(2)–Zn(1)–N(2) 86.02(13)
O(3)–Zn(1)–N(3)ⅲ 98.10(13) O(3)–Zn(1)–N(2) 161.92(13)
O(2)–Zn(1)–N(1) 121.46(13) N(3)ⅲ–Zn(1)–N(2) 99.58(14)
O(3)–Zn(1)–N)–N(1) 90.49(12) N(1)–Zn(1)–N(2) 78.31(13)

Complex 1: Symmetry codes: i −x + 2, y + 1/2, −z + 3/2, ii −x + 2, y − 1/2, −z + 3/2.

Complex 2: Symmetry codes: i x, −y, z − 1/2, ii −x + 1, y, −z + 1/2, ⅲ x, −y, z + 1/2.

X-ray crystallography

X-ray diffraction studies of 1 and 2 were measured on a Rigaku RAXIS-RAPID diffractometer, equipped with graphite-monochromatized Mo-Kα radiation (λ = 0.71073 Å) using the ω scan technique at 296(2)K. The structures were solved using programs named SIR2014 [27] and SHELXL2018/3 [28] and refined by a full-matrix least-squares technique based on F 2. Non-hydrogen atoms were refined with anisotropic displacement parameters, and hydrogen atoms were placed in calculated positions and refined using a riding atom. The disordered solvent water molecules in 2 were taken away by PLATON SQUEEZE [29]. The SQUEEZE calculations make clear that a total disordered solvent accessible area volume is 752 Å3 and the residual electron density is 176 e per unit cell involving about 17 water molecules (about 4.25 water molecules per asymmetric unit). The disordered solvent water molecules’ contributions are not contained in its formula weight. The structure refinement parameters and detailed crystallographic data of 1 and 2 have been collected in the Cambridge Crystallographic Data Center, and CCDC numbers for 1 and 2 are 2304359 and 2304360.

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

  2. Author contributions: Huilin Wang: writing – original draft, experimental work, and editing, Xin Wang: data curation and synthesized, Meimiao Li: investigation, collecting data, and validation, Jindong Feng: supervision and writing – review.

  3. Conflict of interest: Authors state no conflict of interest.

  4. Data availability statement: The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Received: 2023-12-10
Accepted: 2024-03-25
Published Online: 2024-05-20

© 2024 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-2023-0033
Keywords for this article
coordination polymer; Zn(ii); phenanthroline derivatives
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  10. Organodiphosphines in Pt{η2-P(X)nP}(Cl)2 (n = 4, 5, 6, 7, 8, 10, 11, 15, 18) derivates: Structural aspects
  11. Rapid Communications
  12. Two new Zn(ii) coordination polymers incorporating 2-(2,6-dichlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline: Synthesis and structure
  13. Reaction of potassium germabenzenide with benzil: Unusual ring opening to form a unique polycyclic penta-coordinated germanate
  14. Syntheses, structures, and characterization of two new Zn(ii)/Cd(ii) complexes with phenanthroline derivative
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