Synthesis and Photoelectric Properties of Metal–Organic Zeolites Built

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Cite This: Inorg. Chem. XXXX, XXX, XXX−XXX

Synthesis and Photoelectric Properties of Metal−Organic Zeolites Built from TO4 and Organotin Guang-Hui Chen,†,‡ Yan-Ping He,*,‡ Shu-Hua Zhang,† Fu-Pei Liang,*,† Lei Zhang,*,‡ and Jian Zhang‡ †

College of Materials Science and Engineering, Guilin University of Technology, Guilin 541004, P. R. China State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China

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S Supporting Information *

Scheme 1. Schematic Representation of the Synthetic Design and the Valence Sum in a New Type of MOZ

ABSTRACT: Herein we report a novel strategy capable of generating a new class of metal−organic zeolite (MOZ) materials. When the MoO4 or WO4 tetrahedra are employed to assemble with triorganotin R3Sn fragments, four 3D networks with the zeolite BCT topology and nonzeotype 4-connected topological net (such as lon and dia) have been generated. The photocurrent study results show that these materials have good photoelectric response and high photophysical stability.

Z

eolites are one of humanity’s most important microporous materials and have been widely used as adsorbents and catalysts in many important fields.1−7 The basic structural feature of each zeolite framework is its typical 4-connected open framework with TO4 (T = Si4+, Al3+, P5+, etc.) building blocks. To mimic zeolitic SiO2 and AlPO4 frameworks,8−12 metal−organic zeolites (MOZs), including zeolitic imidazolate frameworks (ZIFs)13−21 and boron imidazolate frameworks (BIFs),22−28 have been increasingly developed in recent decades. As a subclass of metal−organic frameworks (MOFs) and metal−organic analogues of zeolites, MOZs integrate the merits of both MOFs and zeolites, for example, high surface area and porosity as well as exceptional stability of the zeolites, and have become one of the most active fields in MOFs. In the latter research, to possess the catalytically active TO4 sites of zeolites and the high porosity of ZIFs, Zhang et al. reported hybrid ZIFs, in which the TO4 units are not traditional SiO4 or AlO4 units in aluminosilicate zeolites but catalytically active MoO4 or WO4 units.29,30 On the basis of previous research, herein we demonstrate a novel strategy capable of generating a new class of MOZ materials. This method is based on the combination of triorganotin R3Sn (R = CnH2n+1, where n ≤ 4) units and TO4 (T = Mo6+ or W6+) units into extended frameworks (Scheme 1), in which each TO4 tetrahedron is connected with four neighbors by sharing their R3Sn units to form a 3D 4connected framework. One advantage of this method is that it endows this MOZ material with catalytically active TO4 sites. Furthermore, unlike traditional zeolites, in which the T···T distance is ∼4 Å, a longer T···T distance (∼8 Å) can be observed through this method. Besides that, the introduction of positively charged R3 Sn units can provide charge compensation for the negatively charged MoO4 or WO4 © XXXX American Chemical Society

units to maintain charge balance. In theory, the resulting MOZ will exhibit zeolitic and nonzeotypic 4-connected topologies. Following the above design strategy, MgMoO4 was solvothermally assembled with n-Bu2SnO or Me3SnCl in the presence of ethylenediamine (en), n-propanol (n-PrOH), and N,N-dimethylformamide (DMF), giving rise to a series of neutral 4-connected frameworks with the zeolite BCT topology and nonzeotype 4-connected topological nets (such as lon and dia; Tables 1 and S1 and Figure 1). Astoundingly, the maximum distance between the two metal centers in the Table 1. Summary of the Compositions and Characteristics of the Compounds complex

composition

space group

network

MOZ-51 MOZ-51(W) MOZ-52 MOZ-52(W) MOZ-53 MOZ-53(W) MOZ-54 MOZ-54(W)

[(C4H9)6Sn2MoO4] [(C4H9)6Sn2WO4] [(CH3)2(C4H9)4Sn2MoO4] [(CH3)2(C4H9)4Sn2WO4] [(CH3)3(C4H9)3Sn2MoO4] [(CH3)3(C4H9)3Sn2WO4] [(C4H9)15Sn5FMo2O8] [(C4H9)15Sn5FW2O8]

I4/mmm I4/mmm P63/mmc P63/mmc Fd3̅m Fd3̅m R3̅m R3̅m

BCT BCT lon lon dia dia dia dia

Received: July 1, 2019

A

DOI: 10.1021/acs.inorgchem.9b01935 Inorg. Chem. XXXX, XXX, XXX−XXX

Communication

Inorganic Chemistry

Figure 1. Coordination environments of the molybdenum(VI) and tin(IV) centers in MOZ-51 (a) and MOZ-54 (b). Mo−O−Sn angles in MOZ51−MOZ-54 and the Sn−F−Sn angle in MOZ-54 (c). Basic building cages in MOZ-51 and MOZ-54 (d and g), respectively, and their topological frameworks with different pore sizes (h−k).

range from 168.895 to 174.775°, which deviates significantly from linearity, and the Mo···Mo distances are ∼8 Å. These geometric parameters are in agreement with those of previously reported trialkyltin-containing polyoxomolybdates.31−37 As a consequence of the linkage of each MoO42− unit by four n-Bu3Sn+ groups, a 3D neutral structure is formed (Figures 1d and S1). The free spaces are occupied by the coordinated Bu groups, all of which are calculated by elemental analysis and thermogravimetric analysis (TGA). There are 3D open channels with a maximum distance between two metal centers of 13.5 Å along the c axis in the inorganic framework. From the viewpoint of topology, the framework of MOZ-51 can be best described as the zeolite BCT topology with a 4connected net (Figure 1h). Herein, we first report such a trialkyltin-containing polyoxomolybdate with zeolite topology. When Me3SnCl and H2O2 were added to the reaction system of MOZ-51, compound MOZ-52 was successfully synthesized. Interestingly, by substituting H2O2 with tert-butyl hydroperoxide (Me3COOH) in the above synthetic procedure for MOZ-52, compound MOZ-53 was obtained. Structure determination of MOZ-52 and MOZ-53 shows that they crystallize in highly symmetric hexagonal and cubic crystal systems with space groups P63/mmc and Fd3̅m, respectively, and their crystal structures also consist of MoO42− units and trialkyltin (Me3Sn+ and n-Bu3Sn+) fragments that are connected by Mo−O−Sn bridges (Figures 1e,f and S3 and

inorganic frame can reach to 11.5−13.5 Å. A large number of coordinated alkyl groups occupying the channels endow these materials with some extent hydrophobicity and very high stability in air. In addition, the phase purities, thermal stabilities, and photocurrent properties of these materials are also investigated. In the presence of en, the reaction of n-Bu2SnO with MgMoO4 in n-PrOH/DMF at 100 °C for 3 days leads to the formation of [(C4H9)6Sn2MoO4] (MOZ-51). Single-crystal Xray diffraction (XRD) reveals that MOZ-51 exhibits a 3D network of MoO42− tetrahedra linked together by n-Bu3Sn+ moieties [except for a coordinated carbon atom, other carbon atoms of butyl (Bu) groups could not be located and squeezed by the PLATON program]. It crystallizes tetragonal in the space group I4/mmm. Mo1, Sn1, Sn2, O1, O2, C1, C2, and C3 are on a mirror plane, and Mo1, Sn1, Sn2, and C2 are also on a 2-fold rotation axis. In this structure, the molybdenum(VI) center is tetrahedrally coordinated by four oxygen atoms (Figure 1a), with the bond lengths (1.722−1.732 Å) and angles (109.032−109.619°) being not unusual for an orthomolybdate. In the case of the bridging n-Bu3Sn+ group (Sn1 and Sn2), the center tin(IV) atom has a distorted trigonal-bipyramidal coordination, with three n-Bu groups occupying the equatorial positions and the molybdate oxygen atoms in the axial positions. The Sn−C bond lengths are in the range of 2.119−2.294 Å, and the Sn−O distance varies from 2.261 to 2.265 Å. It is worth noting that the Mo−O−Sn angles B

DOI: 10.1021/acs.inorgchem.9b01935 Inorg. Chem. XXXX, XXX, XXX−XXX

Communication

Inorganic Chemistry S4). For MOZ-52, Mo1, Sn1, Sn2, O1, O2, C1, and C2 are on a mirror plane. In addition, Sn1, Sn2, and C1 are on a 2-fold rotation axis, and Mo1 and O1 are on a 3-fold axis. Sn1 is also on the 6-fold inversion axis. Also, for MOZ-53, Mo1, Sn1, and O1 are on a mirror plane, and C1 is on a 2-fold axis. In addition, Mo1 and O1 are on a 3-fold axis, and Sn1 is on a three inversion axis. A coordination pattern similar to that of MOZ-51 was also observed in MOZ-52 and MOZ-53 (Figure S2). Different from MOZ-51, a Mo−O−Sn angle of 180° is present in both MOZ-52 and MOZ-53, and half of the coordinated alkyl groups are methyl (Me) groups. In addition, they possess more common nonzeotype 4-connected lon and dia topological nets (Figure 1i,j, respectively). The maximum distance between the two metal centers can reach up to 12.5 Å. However, when HF is added to the synthetic system of MOZ-51, MOZ-54 is produced. X-ray crystallography reveals that MOZ-54 also exhibits a 3D network with dia topology (Figures 1k and S5). It crystallizes trigonal space group R3̅m. Mo1, Sn1, Sn2, O1, O2, and F1 are on a mirror plane. In addition, Mo1, Sn2, and O1 are on a 3-fold rotation axis, and Sn1 is on a 2-fold axis. F1 is also on a 3-fold inversion axis. As seen in Figure 1b, except for introduction of the n-Bu3Sn+ group, an unusual [(n-Bu3Sn)F(n-Bu3Sn)]+ group is observed in this structure. The Sn−F−Sn angle of 180° and the Sn−F bond of 2.149 Å are consistent with those reported for linearsymmetrically bridged chain structures [such as (CH3)3SnF, (C6H11)3SnF, and Ph3SnF].38−40 Consequently, the Mo···Mo distance is up to ∼12 Å (Figure 1c). The ratio of Sn/Mo in these materials can be well proven by scanning electron microscopy−energy-dispersive spectrometry (Figures S6 and S7). TGA curves show that all of the samples have a weight loss of ∼60% after 250 °C (Figures S8, S10, S12, and S14), which is related to the removal of guests and the coordinated alkyl (Me or Bu) groups as well as a small amount of tri-n-butyltin hydride with low boiling point. The residues after decomposition may be Sn, SnO, MoO2, and Mo2C (Figure S21), and the final ratio of Sn/Mo is only 1.5:1, as measured by inductively coupled plasma atomic emission spectroscopy. The powder XRD patterns of compounds MOZ51−MOZ-54 confirmed very high purities on their phase (Figures S9, S11, S13, and S15). Because a large number of alkyl (Me or Bu) groups occupying the channels endow these materials with some extended hydrophobicity, the contact angle between MOZ-51 and H2O is 158° (Figure S16); thus, it is extremely stable in air (Figure S17). In addition, the isostructural compounds MOZ-51(W)−MOZ-54(W) could also be obtained by substituting molybdate for tungstic acid or tungstate in the synthetic procedure, as confirmed by the single-crystal structures (Table S1) and powder XRD patterns (Figures S9, S11, S13, and S15). The photoelectrochemical properties of these materials were studied in a three-electrode system. Upon on−off cycling irradiation with xenon light (intervals of 10 s), obvious photocurrent responses were observed for MOZ-51−MOZ-54 (Figure 2). On the one hand, the cathodic photocurrents were quickly generated and kept stable without an obvious intensity decrease, indicating their good photoelectric response and high photophysical stability. On the other hand, we find that the response effects exhibit the following tendency: MOZ-54 > MOZ-51 > MOZ-52 ≈ MOZ-53. Herein, the presence of Sn− F−Sn bridges in MOZ-54 may result in relatively a high photocurrent response, but other factors (such as topology types or coordinated alkyl groups, etc.) cannot be completely

Figure 2. Procurement responses of MOZ-51−MOZ-54 in a 0.2 M Na2SO4 aqueous solution under repetitive irradiation.

excluded. In addition, we also investigated the photocurrent responses of their isostructural compounds MOZ-51(W)− MOZ-54(W) (Figure S18). Among isostructural compounds, tungsten-containing materials have better photocurrent properties than molybdenum-containing materials, but the opposite result occurs in MOZ-54 and MOZ-54(W). The IR spectra of the samples (MOZ-51 and MOZ-52) after photocurrent studies are similar to those of the original crystals, indicating that they are stable during measurement (Figure S20). These results indicate that these materials should be a suitable candidate for light-harvesting and photoinduced catalysis. In conclusion, a novel synthetic method capable of generating a new class of MOZ materials is proposed herein, and four 3D networks (MOZ-51−MOZ-54) of the MoO42− tetrahedral linked together by trialkyltin moieties have been synthesized through this method. They exhibit zeolite BCT topology and zeolite-like lon and dia networks, respectively. The presence of coordinated alkyl groups occupying the channels endows these materials with some extended hydrophobicity and very high stabilities in air. In addition, the photocurrent study results show that they may have potential applications on light-harvesting and photoinduced catalysis.

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.inorgchem.9b01935. Experimental details, crystallographic studies, additional figures, and general characterization (PDF) Accession Codes

CCDC 1903441−1903448 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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AUTHOR INFORMATION

Corresponding Authors

*E-mail: [email protected]. *E-mail: fliangoffi[email protected]. *E-mail: [email protected]. ORCID

Yan-Ping He: 0000-0001-6004-5153 C

DOI: 10.1021/acs.inorgchem.9b01935 Inorg. Chem. XXXX, XXX, XXX−XXX

Communication

Inorganic Chemistry

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Shu-Hua Zhang: 0000-0002-1097-1674 Fu-Pei Liang: 0000-0001-7435-0140 Lei Zhang: 0000-0001-7720-4667 Jian Zhang: 0000-0003-3373-9621 Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS This work is supported by the NSFC (Grant 21771043) and FJKJT (Grant 2017J06009). REFERENCES

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DOI: 10.1021/acs.inorgchem.9b01935 Inorg. Chem. XXXX, XXX, XXX−XXX