Connected loh1 Topology - American Chemical Society

Article pubs.acs.org/crystal

A Two-Fold Interpenetrated Coordination Framework with a Rare (3,6)-Connected loh1 Topology: Magnetic Properties and Photocatalytic Behavior Yong-Qiang Chen, Sui-Jun Liu, Yun-Wu Li, Guo-Rong Li, Kun-Huan He, Yang-Kun Qu, Tong-Liang Hu, and Xian-He Bu* Department of Chemistry, and Tianjin Key Lab on Metal and Molecule-Based Material Chemistry, Nankai University, Tianjin 300071, China S Supporting Information *

ABSTRACT: A new manganese(II) coordination polymer, [Mn2(L1)4/3(L2)2]n (1) (L1 = 4′-(4-pyridyl)-4,2′:6′,4″-terpyridine, H2L2 = (4-phenyl)-2,6-bis(4-carboxyphenyl)pyridine), has been prepared and structurally characterized. Complex 1 is a 2-fold interpenetrated three-dimensional framework, which to our knowledge represents the first interpenetration example of coordination framework with unique (3,6)-connected loh1 topology. Furthermore, the magnetic properties and photocatalytic activity have been investigated. As a result, complex 1 displays a weak antiferromagnetic interaction among the Mn(II) centers and good photocatalytic activity for the degradation of methyl orange solution under ultraviolet light irradiation.

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INTRODUCTION In recent years, the design and synthesis of coordination polymers (especially for metal−organic frameworks (MOFs) or porous coordination polymers PCPs) still has an upsurge of research interest not only due to their diversity of architectures and fascinating topologies but also for their potential applications in gas storage, ion recognition/separation, catalysis, drug delivery, luminescence, and so on.1,2 Meanwhile, gaining an understanding of network topology represents an important aspect of the synthesis and analysis of coordination polymers (CPs) and also of the inherent interest in explanation of the supramolecular assembly.3,4 For the complicated frameworks, especially for the two- (2D) and three-dimensional (3D) structures, the topological approach is an efficient way in structural simplification and subsequent systematization of CPs by simple node-and-linker reference nets.5 Therefore, CPs with new or unusual networks can be controlled by the deliberate design and judicious choice of the organic ligands. For the mixed connectivity networks containing a 3connected node, the C3-symmetric ligands have been regarded as good candidates to construct 2D subnet tectons with a 63hcb net. As a rigid planar ligand, the triangle ligand 4′-(4pyridyl)-4,2′:6′,4″-terpyridine (L1, see Chart 1) has been rarely used in the realm of MOFs relative to 2,4,6-tris(4-pyridyl)1,3,5-triazine.6 The L1 belongs to an exotridentate ligand, which is more probable to form a 63-hcb 2D subnet. As we know, the frequent (3,6)-connected nets in MOFs are mainly focused on rutile net (rtl, Schläfli symbol (4.62)2(42.610.83), pyrite net (pyr, Schläfli symbol (63)2(612.83), and anatase net © 2012 American Chemical Society

Chart 1. Schematic Representation for the Structures of the Ligands

(ant, Schläfli symbol (42.6)2(44.62.88.10).7 However, the limited (3,6)-connected frameworks for MOFs and inorganic materials have been documented so far.8 What’s more, the 2-fold interpenetrating 3D frameworks with (3,6)-connected topology are even rare. Until now, only seven examples have been reported.9 Moreover, it is known that the degree of interpenetration is a worthy concerning factor in the synthesis progress of MOFs, which plays an important part in determining pore size.10 For the bigger size organic ligands, the interpenetration is a common phenomenon in their coordination architectures. Controlling the interpenetrating degree with the aid of the noncoordinating groups of the Received: July 19, 2012 Revised: September 17, 2012 Published: September 25, 2012 5426

dx.doi.org/10.1021/cg301010x | Cryst. Growth Des. 2012, 12, 5426−5431

Crystal Growth & Design

Article

matrix least-squares methods with SHELXL.18 Metal atoms were located from the E-maps and other non-hydrogen atoms excluded in counterions were located in successive difference Fourier syntheses and refined with anisotropic thermal parameters on F2. A disordered model was used to describe the position C32/N4 and C39/N5 to account for crystallographic symmetry. Further details of crystal data and structure refinement for 1 are summarized in Table 1. CCDC, 873837.

organic ligand is an effective strategy.9f The (4-phenyl)-2,6bis(4-carboxyphenyl)pyridine (H2L2, Chart 1) is a good dicarboxylic acid candidate bearing a phenyl ring. However, as far as we know, MOFs based on H2L2 have never been documented to date. Photocatalysis has been regarded as a green ecological technology for the oxidative degradation of organic dirt in the gas or aqueous phase.11 Recently, considering the novelty of this field in MOFs, much effort has been devoted to developing new photocatalytic materials based on MOFs in the green degradation of many kinds of organic contaminants.12 The most available data about MOFs as a photocatalytic material with semiconductor behavior have been obtained from MOF-5, which is an active photocatalyst for photodegradation of phenol in aqueous solutions.13 Compared to the traditional semiconductor metal oxide, the advantages of MOFs as photocatalyst lie in the fact that their combination of inorganic and organic moieties can result in different metal−ligand charge transfer related tunable photocatalysts.14 Furthermore, a critical factor for the selection of L1 and H2L2 as ligands is their capability of absorbing UV radiations and undergoing photochemical processes upon photoexcitation because of the large conjugated system. On the basis of the above-mentioned points, we present the synthesis and structure of a 3D MOF [Mn2(L1)4/3(L2)2]n (1) with a rare loh1 topology. Importantly, the network is to our knowledge the first interpenetration example of a coordination framework with unique (3,6)-connected loh1 topology.15 Furthermore, the magnetic property and photocatalytic activity for the degradation of methyl orange have also been investigated.

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Table 1. Crystal Data and Structure Refinement for Complex 1 1 empirical formula formula weight temperature wavelength crystal system, space group unit cell dimensions volume Z, calculated density absorption coefficient F(000) goodness-of-fit on F2 final R indicesa [I > 2σ(I)] a

C38H25MnN4O4 656.56 293(2) K 0.71073 Å hexagonal, R3̅ a = b = 27.314(7) Å, c = 22.740(12) Å α = β = 90°, γ = 120° 14692(9) A3 18, 1.333 g/cm3 0.451 mm−1 6066 1.172 R1 = 0.1186, wR2 = 0.2072

R = Σ(∥F0| − |FC∥)/Σ|F0| wR2 = [Σw(|F0|2 − |FC|2)2/(Σw|F0|2)2]1/2.

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RESULTS AND DISCUSSION Description of the Crystal Structures. Complex 1 crystallizes in the hexagonal space group R3̅, and the coordination environment around Mn(II) is shown in Figure 1. The selected bond lengths and angles are summarized in

EXPERIMENTAL SECTION

Materials and Measurements. All the chemicals used for synthesis are of analytical grade and commercially available. L1 and H2L2 were synthesized according to the literature.16 IR spectra were measured on a Tensor 27 OPUS (Bruker) FT-IR spectrometer with KBr pellets. Powder X-ray diffraction (PXRD) spectra were recorded on a Rigaku D/Max-2500 diffractometer at 40 kV, 100 mA for a Cutarget tube and a graphite monochromator. Thermogravimetric (TG) analysis was carried out on a Rigaku standard TG-DTA analyzer with a heating rate of 10 °C min−1 from ambient temperature to 800 °C, an empty Al2O3 crucible was used as reference. Magnetic data were collected using crystals of the samples on a Quantum Design MPMS XL7 SQUID magnetometer. The data were corrected using Pascal’s constants to calculate the diamagnetic susceptibility and experimental correction for the sample holder was applied. UV/vis absorption spectra were measured with a Hitachi U-3010 UV−vis spectrophotometer. Synthesis of [Mn2(L1)4/3(L2)2]n (1). A mixture of MnCl2·4H2O (19.8 mg, 0.1 mmol), L1 (20.8 mg, 0.067 mmol), and H2L2 (40 mg, 0.1 mmol) in 10 mL of component solvent (N,N-dimethyl acetamide/ deionized water/methanol = 1:8:1) was sealed in a Teflon-lined autoclave and heated to 150 °C for 3 days. After the autoclave was cooled to room temperature at 10 °C h−1, yellow block crystals were collected by filtration, washed with 3 × 10 mL of deionized water, and air-dried. Yield: ∼57% based on H 2 L2. Anal. Calcd for C38H25MnN4O4: C, 69.51; H, 3.83; N, 8.53%. Found: C, 69.43; H, 3.96; N, 8.61%. IR (KBr, cm−1): 3123w, 2918w, 2166m, 1589s, 1538s, 1400s, 1218w, 1058m, 1013s, 859s, 814s, 791s, 768s, 705m, 626m. X-ray Data Collection and Structure Determinations. X-ray single-crystal diffraction data of 1 were collected on a Rigaku SCXmini diffractometer with graphite monochromatic Mo−Kα radiation (λ = 0.71073 Å). The program SAINT was used for integration of the diffraction profiles.17 The structure was solved by direct methods using the SHELXS program of the SHELXTL package and refined by full-

Figure 1. The coordination environment of Mn(II) in 1.

Table S1, Supporting Information. In the asymmetric unit, the Mn1 ion and its symmetry-related Mn1(A) are hexacoordinated, which assume identical pseudo-octahedral geometry. The Mn1 ion is supplied by two pyridyl N atoms of two L1 ligands in the axial positions (Mn−N 2.244(7) and 2.245(6) Å) and four oxygen atoms from the carboxylate groups of three unique L2 anions (Mn−O 2.149(6)−2.327(5) Å). Two deprotonated carboxyl groups of each L2 adopt the different coordination modes (bridging-bidentate and chelated-biden5427



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Figure 2. Views of (a) the octahedral cage structure with the six dinuclear Mn2 SBUs as the vertexes; (b) the cage unit along the different axes.

63-hcb net is more common in a 2D framework rather than a 3D array.7d,20 Another important structural feature of complex 1 is that it possesses a nanoscale octahedral cage unit, which is constituted by Mn12 circuit subunit and four L1 ligands (Figure 2, Figure S5). Meanwhile, another column-like nanocage exists along the c axis between two nanoscale octahedral cages in one framework. These nanoscale octahedral cages in another framework are surrounded by such column-like nanocages, and the cavity of nanoscale octahedral cages is occupied by the noncoordination phenyl groups of L2 anions. This feature may endow complex 1 with more chance to assemble the interpenetrated architecture. From the viewpoint of structural topology, if the L1 ligands are considered as 3-connected nodes (extended point symbol is 4.4.4), and the Mn2 SBUs are considered as 6-connected nodes (extended point symbol is 4.4.4.4.4.4.62.62.62.62.64.64.828.828.88) (Figure S6, Supporting Information), the whole 3D structure exhibits a rare (3,6)connected loh1 topology with the vertex symbol (43)2(46.66.83)3 calculated with TOPOS software (Figure 3a).21 Moreover, in order to minimize the void cavities and stabilize the framework, the potential voids were filled by another identical network, which gives an unusual 2-fold interpenetrated 3D framework, and the resulting 2-fold interpenetrating network belongs to class Ia (Figure 3b).21b The 2-fold interpenetrated structure of complex 1 may result from the extended π−π interactions of L1 ligands and the arrangement fashion of noncoordinating phenyl groups of L2. This is the first case of an interpenetrated loh1 network with (3,6)-connected topology. To further study the structure carefully, it can also be considered as a combination of the 2D honeycomb net and a 3D NbO framework (Figure 4). To date, only two (3,6)-connected frameworks with loh1 topology have been observed in coordination polymers. However, compound 1 is clearly different from them, for it is a two-

tate) connecting two neighboring Mn(II) ions to generate the dinuclear Mn2 SBUs with a Mn−Mn distance of 4.001 Å. An attractive structural feature of 1 is that each μ4-bridging L2 ligand links two Mn2 SBUs, and six L2 units connect six dimetal units to form a Mn12 circuit subunit (Figure S1, Supporting Information). All noncoordinating phenyl groups of L2 ligands are arranged along the same direction at the periphery of the Mn12 circuit. Furthermore, the Mn2 SBUs are interconnected by L2 ligands to form a 3D network (Figure S2, Supporting Information). On the basis of the above connection mode, each dinuclear Mn2 connects four adjacent Mn2 SBUs through L2 ligands and can be simplified as a 4-connected node. Thus the network can be described as a uninodal 4connected framework with NbO topology (Schläfli symbol 64.82). According to a previous report, coordination frameworks made from long bridging ligands are easy to give rise to the formation of interpenetrating motifs.19 It is noteworthy that the noncoordinating phenyl groups of L2 ligands are distributed in turn at both sides of Mn-L2 framework. And, the π−π stacking interactions are observed between the noncoordinating phenyl groups and L1 ligands (the face-to-face distance 4.057 Å). As a result, the arrangement fashion of noncoordinating phenyl groups may be an important factor to control the degree of interpenetration of the whole framework. On the other hand, the Mn(II) ions in turn are 3-connected by L1 ligands to form a “honeycomb-like” net with short topological terms of 63-hcb (Figure S3, Supporting Information). In addition, π−π stacking interactions between L1 ligands (the center pyridyl) within the structure of 1 are also found with the face-to-face separation of 3.798 Å. Thus, the L1 ligands are filled in cavity of 3D Mn-L2 structure along the c axis, that is, the stacking fashion of triangle ligands is favorable for adjusting the degree of interpenetration. Finally, a complicated 3D framework was obtained through the 2D honeycomb layer in combination with the 3D NbO structure (Figure S4, Supporting Information). Generally, the 5428



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XRPD and Thermal Analysis. In order to confirm the phase purity of complex 1, the XRPD pattern was characterized. As shown in Figure S7 (Supporting Information), the experimental PXRD pattern of 1 is in good agreement with its corresponding simulated pattern, indicating phase purity of this sample. The TGA curve of 1 showed that it possesses relatively high thermal stability. Herein, a rapid mass loss began at 476 °C, which corresponded to the decomposition of organic ligands (Figure S8, Supporting Information). Photocatalytic Activity. Methyl orange (MO) is a model of dye pollutant, which can be used to evaluate the effectiveness of photocatalysts in the purification of wastewater.12b,22 Moreover, complex 1 is water-insoluble photocatalyst. Thus, the photocatalytic activity of as-prepared 1 was tested by the degradation of MO solution under ultraviolet (UV) light irradiation. To our knowledge, TiO2 has been studied extensively as a semiconductor photocatalyst. However, a main drawback for its application in wastewater treatment is difficult in the separation of suspended TiO2 fine particle. Although TiO2 is usually immobilized onto substrates for practical use, a significant loss of activity was generally reported due to greatly reduced surface area after immobilization.23 In the process of photocatalysis, 65 mg complex 1 was suspended in 1.71 × 10−5 mol/L MO aqueous solution 300 mL, then magnetically stirred in the dark for about 30 min to ensure the establishment of an adsorption/desorption equilibrium. After that, the mixture was stirred and continuously exposed to UV irradiation from a 500 W high pressure mercury vapor lamp. A sample was taken every 15 min from the vessel, and subsequently analyzed by UV−visible spectroscopy (Figure 5). For comparison, the photodegradation process of MO without any photocatalyst has also been studied under the same conditions (Figure S11, Supporting Information). As illustrated in Figure 6, the change in the concentration of MO solution is obvious with the use of complex 1 as photocatalyst. It can be seen that approximately 40% of MO has been decomposed after 1.5 h of irradiation. The result indicates that complex 1 is active for the decomposition of MO under UV light irradiation. Meanwhile, the photocatalytic performance of 1 is superior to the compound (H2bix)2(NaHP2Mo5O23)·2H2O (bix = 1,4-

Figure 3. Views of (a) the (3,6)-connected loh1 net with (43)2(46.66.83)3 topology; (b) the 2-fold interpenetrated framework for 1.

penetrating framework constructed from the long “V” shape bridging dicarboxylate and the triangle L1 ligand.

Figure 4. Schematic representation of the possible procedure for assembling loh1 topology. 5429



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CONCLUSIONS A new 2-fold interpenetrated 3D coordination framework with rare (3,6)-connected loh1 topology has been successfully prepared based on triangle L1 and “V” shape L2 ligands. The complex 1 obtained reveals the mixed connectivity networks with 3-connected node and the degree of interpenetration can be efficiently controlled by the rational selection of organic ligands. Moreover, complex 1 exhibits the antiferromagnetic behavior and photocatalytic activity for the degradation of MO solution under ultraviolet light irradiation.

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ASSOCIATED CONTENT

* Supporting Information S

X-ray crystallographic data for complex 1 in CIF format, selected bond lengths and angles, general characterizations (PXRD, IR, and TGA), and additional structure figures. These materials are available free of charge via the Internet at http:// pubs.acs.org.

Figure 5. Absorption spectra of the MO solution during the decomposition reaction with the use of complex 1.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Fax: +86-22-23502458. Tel: +86-22-23502809. Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS This work was supported by the National Science Foundation of China (21031002 and 51073079), the National Basic Reaseach Program of China (973 Program, 2012CB821700), and the Natural Science Fund of Tianjin, China (10JCZDJC22100).

Figure 6. Photocatalytic decomposition of MO solution with the changes in Ct/C0 plot of complex 1, and black curve is the control experiment without any catalyst.

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bis(imidazol-1-ylmethyl)benzene) for the decomposition of rhodamine B under UV irradiation (approximately 36%).24a The differences of photocatalytic activities of MOFs may result from the different central metals, the selection of organic ligands, and the final framework structures of the complex.24b During the photocatalytic process of 1, the central Mn(II) ions and the ligands are involved. UV−visible light induce L1 ligands and L2 anions to produce O and/or N−Mn(II) charge transfer promoting electron from the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO). In order to return to its stable state for HOMO, the charge transfer excited state (L1* and L2*) was oxygenated water molecules to generate the •OH radicals.24 Thus, the •OH active species could decompose the MO to complete the photocatalytic process. In order to evaluate reproducible ability of complex 1, the repeated photocatalysis experiment was also studied with a constant MO concentration. After each cycle of MO photodegradation, complex 1 was separated and washed with water. As shown in Figure S12, there is no significant reduction of decolorization rate when the photocatalyst is used for five times in the same photodegradation process. The result indicated that the photocatalytic activity of 1 has a good reproducibility. After photocatalysis, the PXRD pattern was nearly identical to that of the original complex, implying that 1 can be used as a stable photocatalyst. 5430



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Connected loh1 Topology - American Chemical Society

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