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Crystal structure and physical properties of a new two-dimensional zinc coordination polymer based on 1,4-bis(4-(imidazole-1-yl)benzyl)piperazine and benzophenone-2,4′-dicarboxylate ligands

  • Xin-Yue Zhang , Chen Zhang , Jun Wang and Xiao-Juan Xu EMAIL logo
Published/Copyright: June 10, 2021
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 76 Issue 6-7

Abstract

A new 2-dimensional (2D) zinc(II) coordination polymer based on a flexible bis(imidazole) ligand, namely, [Zn2(BIBP)(BPDC)2·DMF]n (1) BIBP is 1,4-bis(4-(imidazole-1-yl)benzyl)piperazine and H2BPDC is benzophenone-2,4′-dicarboxylic acid), has been synthesized and characterized through single-crystal X-ray diffraction, infrared (IR) spectroscopy, and elemental and thermal gravimetric analysis. Complex 1 exhibits a 2D framework oriented parallel to [0 2 1] based on [Zn(BPDC)]n chains. The fluorescence and catalytic properties of complex 1 for the photodegradation of methylene blue were investigated.

Keywords: benzophenone-2,4′-dicarboxylate; 1,4-bis(4-(imidazole-1-yl)benzyl)piperazine; coordination polymer; luminescence property; photocatalytic activity; zinc(II)

1 Introduction

The assembly and design of coordination polymers (CPs) based on metal centers as nodes and their linking by organic ligands have been a crucial subject in the areas of crystal engineering and material science, not only from their sublime topological structures but also from their diverse practical applications in the fields of catalysis, luminescence, molecular recognition, gas adsorption/separation, and magnetic materials [1], [2], [3], [4], [5]. The many factors that can determine the structure of the complex include the solvent, the pH value, the counter ions, and the reaction temperature for preparation [6], [7], [8]. There is no doubt that the choice of organic ligands, which can change the structure of CPs, is more vital than these external elements [9], [10]. The flexible imidazole ligand 1,4-bis(4-(imidazole-1-yl)benzyl)piperazine (BIBP) has been used to construct polymer architectures with different conformations consistent with the geometric requirements of diverse metal atoms [11], [12]. On the other hand, the dianion of benzophenone-2,4′-dicarboxylic acid (H2BPDC) as an asymmetrical V-shaped ligand has received less attention in the construction of coordination polymers [13], [14]. Based on the aforementioned consideration, in this work, we selected H2BPDC as the organic carboxylate ligand and simultaneously introduced BIBP as the auxiliary ligand to react with Zn(II) ions under solvothermal conditions. A new two-dimensional (2D) coordination polymer, [Zn2(BIBP)0.5(BPDC)·DMF]n (1) has been synthesized and characterized by infrared (IR) spectroscopy and elemental and thermal analysis. Complex 1 displays fluorescence and catalytic properties to photodegradate methylene blue (MB).

2 Experimental

2.1 Chemicals and reagents

All starting materials and solvents were commercially available and used without any further purification.

2.2 Physical measurements

The Vario EL III elemental analyzer was used for the elemental analysis of carbon, hydrogen, and nitrogen. Infrared spectra were recorded from KBr pellets in the range from 4000 to 400 cm−1 on a VECTOR 22 spectrometer. Thermal gravimetric analyses (TGAs) were executed on a Perkin-Elmer Pyris 1 Thermogravimetric analyzer from room temperature to 800 °C with a heating rate of 20 K min−1 under nitrogen gas flow. Fluorescence spectra were recorded on a Perkin Elmer LS 55 fluorescence spectrometer. The UV–Vis absorption spectra of aqueous MB solutions were recorded on a Perkin Elmer Lambda 25 spectrophotometer.

2.3 Synthesis of complex 1

A mixture of H2BPDC (22.1 mg, 0.1 mmol), BIBP (39.8 mg, 0.1 mmol), Zn(NO3)2·6H2O (29.7 mg, 0.1 mmol), and DMF (6 mL) was placed in a Teflon-lined stainless steel vessel, heated to 150 °C for three days, and then, cooled to room temperature over 24 h. Colorless crystals of 1 were obtained. The yield was 51% based on Zn(NO3)2·6H2O. Elemental analysis (%) was calculated for C57H49N7O11Zn2: C 60.11, H 4.34, N 8.61; found C 60.28, H 4.34, N 8.63. The IR analysis results are as follows (cm−1): 3440 w, 3131 m, 2937 w, 2812 m, 2685 w, 1622 s, 1523 s, 1360 s, 1303 s, 1128 m, 1064 m, 1011 w, 935 m, 843 s, 738 s, 653 w, 525 w, 461 w.

2.4 Measurement of the photocatalytic effect

The potential of complex 1 as a photocatalyst was evaluated via the degradation of MB under a 300-W medium-pressure Mercury vapor lamp. Thirty milligrams of complex 1 and 10 µL of 30% H2O2 were added into 50 mL aqueous MB solution (10 mg L−1). Prior to irradiation, the solution was magnetically stirred in the dark for 30 min to ensure the establishment of an adsorption/desorption equilibrium. The MB concentration was determined at the maximum absorbance at 664 nm. At a given interval, 1 mL of the reaction solution was periodically taken and analyzed with a UV/Vis spectrophotometer.

2.5 X-ray crystallography

The diffraction data for complex 1 were collected on a Bruker SMART APEX II CCD-based diffractometer using graphite-monochromatized MoKα radiation (λ = 0.71073 Å) with ω − 2θ scan mode at T = 291 K. A semiempirical absorption correction was applied by using the program Sadabs [15]. The structure was solved by direct methods and then refined through full-matrix least-squares techniques using Shelxl-2014 [16]. All nonhydrogen atoms were located in difference Fourier maps and refined anisotropically. The H atoms were placed at calculated positions and refined using a riding model. In complex 1, elongated displacement ellipsoids of all atoms of the DMF solvate molecule suggested disorder. It was modeled successfully as a split-atom model with a refined occupancy ratio of 0.5:0.5. The crystallographic data are summarized in Table 1. Selected bond lengths and angles are given in Table 2.

Table 1:

Crystal data and numbers pertinent to data collection and structure refinement of 1

Empirical formulaC57H49N7O11Zn2
Formula weight1138.81
Crystal systemtriclinic
Space groupP1¯; (no. 2)
a (Å)8.7918(16)
b (Å)12.374(2)
c (Å)13.554(3)
α (°)68.410(4)
β (°)73.792(4)
γ (°)80.998(4)
V (Å3)1314.2(4)
Z1
Dcalcd. (g cm−3)1.44
F(000), e588
μ(MoKα) (mm−1)1.0
θ range (°)1.77 ≤ θ ≤ 26.00
hkl range±10, ±15, ±16
Refl. measured11,440
Refl. unique/Rint5163/0.0286
Param. refined370
R1/wR2 [I > 2 σ(I)]a,b0.0336/0.0677
R1/wR2 (all data)a,b0.0433/0.0710
GoFc (F2)1.092
Δρfin (max/min), e Å−30.26/−0.31

  1. aR1 = Σ||Fo| – |Fc||/Σ|Fo|; bwR2 = [Σw(Fo2 – Fc2)2/Σw(Fo2)2]1/2, w = [σ2(Fo2) + (AP)2 + BP]−1, where P = (Max(Fo2, 0) + 2Fc2)/3; cGoF = S = [Σw(Fo2 – Fc2)2/(nobs – nparam)]1/2.

Table 2:

Selected bond lengths (Å) and angles (°) for 1.

Zn(1)–N(1)1.9971(17)Zn(1)–O(1)2.0858(14)Zn(1)–O(2A)2.0376(15)
Zn(1)–O(3B)2.0206(15)Zn(1)–O(4C)2.0251(16)
N(1)–Zn(1)–O(1)97.86(6)N(1)–Zn(1)–O(2A)103.46(7)N(1)–Zn(1)–O(3B)100.27(7)
N(1)–Zn(1)–O(4C)101.94(7)O(1)–Zn(1)–O(2A)158.67(6)O(1)–Zn(1)–O(3B)91.81(6)
O(1)–Zn(1)–O(4C)84.70(6)O(3B)–Zn(1)–O(2A)85.02(7)O(3B)–Zn(1)–O(4C)157.78(7)
O(4C)–Zn(1)–O(2A)90.29(7)

  1. Symmetry transformations used to generate equivalent atoms: A –x + 1, –y + 1, –z; B –x, –y + 1, –z; C x + 1, y, z.

CCDC 1983253 contains the supplementary crystallographic data for this article. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

3 Results and discussion

3.1 Description of the structure

As revealed by the crystal structure determination, complex 1 displays a 2D coordination framework and crystallizes in the triclinic space group P1¯; with Z = 1. The asymmetric unit contains one Zn(II) ion, one fully deprotonated BPDC2− ligand, one half BIBP ligand, and one half disordered DMF solvate molecule. As is shown in Figure 1, Zn1 lies in a slightly distorted square pyramidal geometry, where the basal plane contains four carboxylate oxygen atom donors (O1, O2A, O3B, and O4C) from four different BPDC2− ligands and in the apical position is an imidazole nitrogen atom (N1) (Symmetry code: A = –x + 1, –y + 1, –z; B = –x, –y + 1, –z; C = x + 1, y, z). The Zn–O bond lengths vary from 2.0206(15) to 2.0858(14) Å, the Zn–N bond lengths are 1.9971(17) Å, and the largest bond angle around the Zn(II) ion is 158.67(6)°, which all fall in expected ranges.

Figure 1: The coordination environment of Zn(II) in complex 1 (symmetry codes: (A): –x + 1, –y + 1, –z; (B): –x, –y + 1, –z; (C): x + 1, y, z.).
Figure 1:

The coordination environment of Zn(II) in complex 1 (symmetry codes: (A): –x + 1, –y + 1, –z; (B): –x, –y + 1, –z; (C): x + 1, y, z.).

In complex 1, each H2BPDC ligand is completely deprotonated and links four Zn(II) atoms in (κ1–κ1)–(κ1–κ1)–μ4 coordination mode. Two independent Zn atoms are bridged by four carboxylate groups of the BPDC2− ligand in a bidentate bridging mode to form a flywheel-shaped dimeric unit [Zn2(COO)4] with a Zn···Zn distance of 2.997(6) Å. The [Zn2(COO)4] dimer is situated about a crystallographic inversion center. Adjacent dimers are connected by BPDC2− ligands to form a 1-D [Zn(BPDC)]n chain (Figure 2). Furthermore, these [Zn(BPDC)]n chains are connected by the BIBP ligands to generate a 2D framework oriented parallel to [0 2 1] (Figure 3). In the Cambridge structural database (CSD) [17], more than 130 examples of carboxylate-bridged Zn2 dimers are documented. Typical complexes are [Zn2(mfda)2(L2)] · DMF · H2O (mfda = 9,9-dimethylfluorene-2,7-dicarboxylate anion, L2 = 4,4′-bipyridine), [Zn2(mfda)2(L3)(H2O)] · DMF (mfda = 9,9-dimethylfluorene-2,7-dicarboxylate anion, L3 = 2,5-bis(4-pyridyl)-,3,4-ocadiazole), [Zn2(mfda)2(L4)] (mfda = 9,9-dimethylfluorene-2,7-dicarboxylate anion, L4 = 1,4-bis(imidazol-1-ylmethyl)benzene), to name but a few examples [18], [19], [20], [21], [22], [23], [24]. Compared with these complexes, the Zn···Zn distance in complex 1 is the shortest.

Figure 2: View of the [Zn(BPDC)]n chain in complex 1.
Figure 2:

View of the [Zn(BPDC)]n chain in complex 1.

Figure 3: View of the 2D structure of complex 1 in the crystal.
Figure 3:

View of the 2D structure of complex 1 in the crystal.

3.2 Thermal analysis

The thermal stability of complex 1 was investigated using thermal gravimetric analysis. The TGA curve of complex 1 exhibits three main steps of weight losses. As shown in Figure 4, the lattice DMF molecules are lost from T = 115–313 °C (calculated: 6.42%, found: 6.7%). The following two steps are attributed to the decomposition of the BIBP ligands and BPDC2− anions. At T = 510 °C, the remaining weight (14.5%) corresponds to ZnO (calculated: 14.30%).

Figure 4: Thermogravimetric curve of complex 1.
Figure 4:

Thermogravimetric curve of complex 1.

3.3 Infrared spectroscopy

The infrared spectrum of complex 1 is consistent with its crystal structure. The absence of such bands at around 1700 cm−1 indicates the complete deprotonation of H2BPDC. For complex 1, the strong vibrations at 1622 and 1523 cm−1 correspond to the asymmetric stretching vibration of the –COO– group, whereas its symmetric stretching vibrations appear at 1360 and 1303 cm−1. The difference in frequency between the asymmetric and symmetric stretching vibrations is more than 200 cm−1, indicating the bidentate-bridging coordination mode of the –COO– group [25].

3.4 Photoluminescence properties

Considering the excellent luminescence properties of some coordination polymers containing d10 metal centers, the solid-state photoluminescence properties of H2BPDC, BIBP, and complex 1 were investigated at room temperature. H2BPDC and BIBP show emission bands at 394 nm (λex = 280 nm) and 315 nm (λex = 278 nm), respectively, which originate from the intraligand π* → n or π* → π transitions [11], [12], [13], [14]. As is shown in Figure 5, there is an emission peak at 394 nm (λex = 246 nm) for complex 1, probably originating from the ligand-based luminescence of BPDC2−. Compared with the free BIBP ligand, the visible red shift of 79 nm for 1 may be attributed to the coordination of BIBP to Zn2+ [26].

Figure 5: The solid-state luminescence spectra of H2BPDC, BIBP, and complex 1 at room temperature (Ex = excitation, Em = emission).
Figure 5:

The solid-state luminescence spectra of H2BPDC, BIBP, and complex 1 at room temperature (Ex = excitation, Em = emission).

3.5 Photocatalytic properties

MB as one of the important dyes is a good model of contaminants because it is highly soluble in water and persistent in the environment. Therefore, we chose MB as a model pollutant in water to investigate the photocatalytic performance of complex 1. As shown in Figure 6, the characteristic absorption peak of MB (663 nm) decreased during the decomposition reaction in the presence of complex 1. As shown in Figure 7, the photocatalytic efficiency of complex 1 on MB reached 84% and that of the blank control group was only 13% within 90 min, indicating that complex 1 has a catalytic activity for the degradation of MB.

Figure 6: UV/Vis absorption spectra of an aqueous MB solution during the decomposition reaction in the presence of complex 1.
Figure 6:

UV/Vis absorption spectra of an aqueous MB solution during the decomposition reaction in the presence of complex 1.

Figure 7: Photocatalytic decomposition rate of the MB solution under UV irradiation.
Figure 7:

Photocatalytic decomposition rate of the MB solution under UV irradiation.

4 Conclusions

In this article, a new 2D zinc(II) coordination polymer constructed from BIBP and H2BPDC was synthesized under hydrothermal condition. This complex represents a 2D framework orientated parallel [0 2 1] based on [Zn(BPDC)]n chains. Complex 1 shows solid-state fluorescence at room temperature and could be a promising candidate for a photoactive material to its catalytic activity in the photodecomposition of MB.

Corresponding author: Xiao-Juan Xu, College of Pharmacy, Yancheng Teachers University, Yancheng, Jiangsu224051, P. R. China, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2020-07-31
Accepted: 2020-11-18
Published Online: 2021-06-10
Published in Print: 2021-07-27

© 2021 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

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  2. In this issue
  3. Research Articles
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  8. Intermetallic phases in the Sc–Ir–In system – synthesis and structure of Sc1.024Ir2In0.976 and Sc3Ir1.467In4
  9. Crystal structure and physical properties of a new two-dimensional zinc coordination polymer based on 1,4-bis(4-(imidazole-1-yl)benzyl)piperazine and benzophenone-2,4′-dicarboxylate ligands
  10. A new N-oxide benzylisoquinoline alkaloid isolated from the leaves of atemoya (Annona cherimola × Annona squamosa)
  11. One-pot synthesis of 1-(benzothiazolylamino)aryl methyl-2-naphthols and 3-benzothiazolyl 2,3-dihydroquinazolinones using a magnetically recoverable core–shell nanocomposite as catalyst
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  13. Facile decoration of CdS nanoparticles on TiO2: robust photocatalytic activity under LED illumination
  14. Book Review
  15. A. Sigel, E. Freisinger and R. K. O. Sigel (Editors and Series Editors): Metal Ions in Bio-Imaging Techniques: Volume 22 of the series Metal Ions in Life Sciences
https://doi.org/10.1515/znb-2020-0137
Keywords for this article
benzophenone-2,4′-dicarboxylate; 1,4-bis(4-(imidazole-1-yl)benzyl)piperazine; coordination polymer; luminescence property; photocatalytic activity; zinc(II)

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research Articles
  4. Synthesis and structure of the λ6Si-silicate [Cs(18-crown-6)]2[Si(OSO2CH3)6]
  5. Approximate estimation of the critical diameter in Koenen tests
  6. Laves phases forming in the system ScCo2-“InCo2”-TaCo2
  7. Magnesium intermetallics: synthesis and structure of Eu2Pt2Mg and Sr2Pt2Mg
  8. Intermetallic phases in the Sc–Ir–In system – synthesis and structure of Sc1.024Ir2In0.976 and Sc3Ir1.467In4
  9. Crystal structure and physical properties of a new two-dimensional zinc coordination polymer based on 1,4-bis(4-(imidazole-1-yl)benzyl)piperazine and benzophenone-2,4′-dicarboxylate ligands
  10. A new N-oxide benzylisoquinoline alkaloid isolated from the leaves of atemoya (Annona cherimola × Annona squamosa)
  11. One-pot synthesis of 1-(benzothiazolylamino)aryl methyl-2-naphthols and 3-benzothiazolyl 2,3-dihydroquinazolinones using a magnetically recoverable core–shell nanocomposite as catalyst
  12. An efficient click synthesis of chalcones derivatized with two 1-(2-quinolon-4-yl)-1,2,3-triazoles
  13. Facile decoration of CdS nanoparticles on TiO2: robust photocatalytic activity under LED illumination
  14. Book Review
  15. A. Sigel, E. Freisinger and R. K. O. Sigel (Editors and Series Editors): Metal Ions in Bio-Imaging Techniques: Volume 22 of the series Metal Ions in Life Sciences
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