Startseite Synthesis, Crystal Structure and Spectroscopic Analysis of a New Sodium Coordination Polymer
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Synthesis, Crystal Structure and Spectroscopic Analysis of a New Sodium Coordination Polymer

  • Tai Xi-Shi EMAIL logo , Meng Qing-Guo und Liu Li-Li
Veröffentlicht/Copyright: 30. Dezember 2016
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Aus der Zeitschrift Open Chemistry Band 14 Heft 1

Abstract

A new sodium coordination polymer, [Na2(L)2(H2O)4]n (1), was synthesized by reflux reaction of p-aminobenzene sulfonic acid, p-hydroxy benzaldehyde and NaOH in ethanol/water solution and characterized by elemental analysis, UV-vis, IR and X-ray single crystal diffraction analysis. The crystal of 1 belongs to monoclinic, space group P21/c with a = 17.765(4) Å, b =10.181(2) Å, c = 8.0450(16) Å, β = 91.67(3)°, V = 1454.5(5) Å3, Z = 4, Dc = 1.531 mg·, μ = 0.28 mm-1, F(000) = 696, and final R1 = 0.0327, ωR2 = 0.0854. The molecules of 1 are extended to a 2D layer structure along ab plane. The 2D layers form 3D framework structure by the interaction of π-π stacking and hydrogen-bond interaction.

Keywords: p-Aminobenzene sulfonic acid; p-hydroxy benzaldehyde; synthesis; crystal structure; spectroscopic analysis

1 Introduction

In recent years, design and synthesis of novel coordination polymers have received much more attention than ever before [1-7]. The coordination polymers have potential applications in many aspects, such as gas storage, fluorescent, catalysis, separation, biological activity and so on [8-11]. Many coordination polymers with various structures and properties have been synthesized and reported [12-15]. Metal ions and ligands play an important role in the construction of coordination polymers. As an important kind of ligand, aromatic sulfonic acid derivates have been extensively used in the synthesis of coordination polymer materials due to their various coordination modes and thermal stability [16-18].

In this paper, a new sodium coordination polymer, [Na2(L)2(H2O)4]n (1), has been synthesized with p-aminobenzene sulfonic acid, p-hydroxy benzaldehyde and NaOH as raw material. Furthermore, the sodium coordination polymer has also been characterized by elemental analysis, IR spectrum, UV-vis spectrum, and single crystal X-ray crystallography.

2 Experimental Section

2.1 Materials and Instrumentation

p-Aminobenzene sulfonic acid, 4-benzoylbenzoic acid, NaOH and solvents were purchased commercially and used without further purification. The IR spectrum was recorded in the range 4000–400 cm-1 on an infrared spectrophotometer (Beijing Purkinje General Instrument, Beijing, MA, China). UV-vis spectrum was obtained from UV-visible spectrophotometer (Beijing Purkinje General Instrument, Beijing, MA, China). Single crystal data of the sodium coordination polymer were collected by a Bruker smart CCD diffractometer (Bruker, Billerica, MA, USA).

2.2 Synthesis of [Na2(L)5((H2O)4]]n(1)

A mixture of p-aminobenzene sulfonic acid (173 mg, 1.0 mmol), 4-benzoylbenzoic acid (150 mg, 1.0 mmol), and NaOH (40 mg, 1.0 mmol) were dissolved in 15 mL mixed solvents of H2O:CH3CH2OH (v:v = 1:2). The mixture was stirred for 6 h at 60 °C, and then colorless crystals were collected and dried in the air.

2.3 Crystal Structure Determination

A colorless single crystal of sodium coordination polymer 1 with dimensions of 0.21 mm × 0.18 mm × 0.17 mm was selected and mounted on a glass fiber for data collection. The X-ray diffraction data were measured at 293(2) K on a Bruker Smart CCD diffractometer with a graphite-monochromatized MoKβ (λ = 0.71073 Å) radiation. The structure was solved by direct methods with SHELXL-97 [19] and refined on F2 by full-matrix least-squares procedures with SHELXTL-97 [20]. The crystal data of 1 are given in Table 1.

Table 1

Crystal data for 1.

Empirical FormulaC13H14NNaO6S
Formula weight335.3
Temperature/K293(2)
Crystal systemMonoclinic
Space groupP21/c
a/Å17.765(4)
b/Å10.181(2)
c/Å8.0450(16)
β/°91.67(3)
Volume/Å31454.5(5)
Z4
ρcalc mg/mm31.531
μ/mm-10.28
S1.02
F(000)696
Index ranges-21≤ h ≤ 21
-12 ≤ k ≤ 12
-9≤ l ≤ 9
Reflections collected10736
Reflections with /> 2σ(l)2561
Independent reflections2257 [R(int) = 0.034
Data/restraints/parameters2561/5/199
Goodness-of-fit on F21.022
Final R indexes [≥2σ(l)]R1 = 0.0327, wR2 = 0.0854
Final R indexes [all data]R1 = 0.0367, wR2 = 0.0893
Largest diff. peak/hole/e Å-30.36/-0.23

3 Results and Discussion

3.1 Elemental Analysis

Anal. Calcd. (%) for C13H14NNaO6S: C, 46.53; H, 4.18; N, 4.18. Found (%): C, 46.72; H, 4.46; N, 4.28. The result of elemental analysis shows that the symmetric unit of Na(I) coordination polymer conforms to 1:1 metal-to-ligand stoichiometry.

3.2 Description of 1

The result of X-ray diffraction reveals that the sodium coordination polymer 1 crystallizes in monoclinic P21/c space group. The coordination environment of sodium ion of 1 is shown in Figure 1. The connection mode of sodium ion is shown in Figure 2. Figure 3 is the 2D layer of sodium coordination polymer 1 along bc plane. Figure 4 is the 3D network structure of the sodium coordination polymer 1. From Figure 1, the asymmetrical unit contains one sodium ion, two new ligands and four coordinated H2O molecules. In 1, sodium ion is six-coordination and resides in a octahedral environment defined by three oxygen atoms (O2, O4) from two new ligands, and other four oxygen atoms (O1W, O1WA, O2W, O2WA) from four coordinated H2O molecules, and two coordinated H2O (O1W, O1WA) were shared with another sodium ion (Na1b), the remaining oxygen atoms (O2W, O2WA) were shared with other two sodium ions (Na1c, Na1d), respectively. Four oxygen atoms (O2W, O2WA, O1W, O2) are at the equatorial plane of this octahedral, and the rest two oxygen atoms (O1W, O4) are at the axle of the octahedral, the angle O4-Na1-O1W is 164.313(54)°. The sodium ions in 1 are linked with the neighboring sodium ions through the bridging effect of oxygen atoms, and forming four-member rings and six-member rings (Figure 2). The sodium coordination polymer 1 is extended to a 2D layer structure along the ab plane (Figure 3). The 2D layers form 3D framework structure by the interaction of π-π stacking and hydrogen-bond interaction. The oxygen atom of phenolic hydroxyl does not coordinate to Na(I), but phenolic hydroxyl group plays an important role in the stability of the structure by hydrogen bonds (Figure 5). The main bond lengths (Å) and angles (°) for 1 are given in Table 2.

Figure 1 The coordination environment of Na(I) in 1.
Figure 1

The coordination environment of Na(I) in 1.

Figure 2 The connection mode of Na(I) in 1.
Figure 2

The connection mode of Na(I) in 1.

Figure 3 2D layered structure of Na(I) coordination polymer.
Figure 3

2D layered structure of Na(I) coordination polymer.

Figure 4 3D network structure by the interaction of 2D layer.
Figure 4

3D network structure by the interaction of 2D layer.

Figure 5 The hydrogen bonds in Na(I) coordination polymer.
Figure 5

The hydrogen bonds in Na(I) coordination polymer.

Table 2

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

BondDistanceBondDistance
N1–C71.268 (3)O1W–Na1[i]2.3850 (15)
N1–C81.418 (2)O1W–Na12.5705 (16)
S1–O21.4496 (13)O2–Na12.3981 (15)
S1–O41.4505 (13)O4–Na1[iii]2.4196 (14)
S1–O31.4611 (13)Na1–O1W[i]2.3850 (15)
S1–C111.7704 (17)Na1–O4[ii]2.4196 (14)
O1–C11.368 (2)Na1–O2W[iii]2.4700 (15)
Angle°Angle°
Na1[i]–O1W–Na198.40 (5)O1W[i]–Na1–O285.81 (5)
Na1[i]–O1W–H1WB122.4O1W[i]–Na1–O4[ii]109.13 (6)
Na1–O1W–H1WB102.1O2–Na1–O4[ii]108.14 (5)
Na1[i]–O1W–H1WA108.1O1W[i]–Na1–O2W[iii]164.82 (6)
Na1–O1W–H1WA118.3O2–Na1–O2W[iii]86.39 (5)
Na1[ii]–O2W–Na1123.00 (6)O4[ii]–Na1–O2W[iii]85.69 (5)
Na1[ii]–O2W–H2WB109.6O1W[i]–Na1–O2W76.74 (5)
Na1–O2W–H2WB104.6O2–Na1–O2W159.74 (5)
Na1[ii]–O2W–H2WA104.6O4[ii]–Na1–O2W87.51 (5)
Na1–O2W–H2WA107.1O2W[iii]–Na1–O2W108.08 (5)
O2W[iii]–Na1–O1W84.59 (5)O1W[i]–Na1–O1W81.60 (5)
O2W–Na1–O1W83.84 (5)O2–Na1–O1W83.51 (5)
S1–O4–Na1[iii]144.73 (8)O4[ii]–Na1–O1W164.31 (5)

3.3 IR Spectrum

Figure 6 shows the IR spectrum of the sodium coordination polymer. From Fig.6, it can be seen that the asymmetrical stretching vibration of C-H in methylene and O-H stretching of inner hydroxyl groups are at 2902 cm-1 and 3442 cm-1, respectively, indicating that the coordination polymer contains water molecules. The asymmetrical stretching of C=C in benzene is at 1493 cm-1, the symmetrical stretching vibration of C-N and symmetrical deformation vibration of N-H in secondary amine are at 1230 cm-1 and 1567 cm-1, respectively. The symmetrical stretching vibration and asymmetrical stretching vibration of sulfonate are at 1041 cm-1 and 1156 cm-1 [21, 22]. The stretching vibration of C-O in phenol is at 1243 cm-1.

Figure 6 IR spectrum of 1.
Figure 6

IR spectrum of 1.

3.4 UV-vis Spectrum

Figure 7 is the UV-vis spectrum of the sodium coordination polymer. The absorption spectrum shows that the maximum absorption peak of the sodium coordination polymer was located at 312 nm, which can be assigned to intraligand π-π* transitions [23].

Figure 7 The UV-vis spectrum of 1.
Figure 7

The UV-vis spectrum of 1.

4 Conclusions

In this paper, a new sodium coordination polymer was synthesized by p-aminobenzene sulfonic acid and p-hydroxy benzaldehyde. And it was characterized by elemental analysis, IR, UV-vis and X-ray single-crystal diffraction. The results showed that the sodium coordination polymer is extended to a 2D layer structure along ab plane. The 2D layers form 3D framework structure by the interaction of π-π stacking and hydrogen-bond interaction.

Acknowledgments

This project was supported by the National Natural Science Foundation of China (No. 21171132), the National Natural Science Foundation of Shandong (ZR2014BL003), the Project of Shandong Province Higher Educational Science and Technology Program (J14LC01) and Science Foundation of Weifang.

Supplementary Materials

Crystallographic data for the structure reported in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No.CCDC 1482473. Copy of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44-1223-336-033; E-Mail: deposit@ccdc.cam.ac.uk).

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Received: 2016-9-30
Accepted: 2016-11-17
Published Online: 2016-12-30
Published in Print: 2016-1-1

© 2016 Tai Xi-Shi, Meng Qing-Guo, Liu Li-Li

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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https://doi.org/10.1515/chem-2016-0031
Schlagwörter für diesen Artikel
p-Aminobenzene sulfonic acid; p-hydroxy benzaldehyde; synthesis; crystal structure; spectroscopic analysis
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Heruntergeladen am 29.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/chem-2016-0031/html
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