Solvent-Dependent Formation of Cd(II) Coordination Polymers Based

Jul 3, 2012 - Interfaces, ACS Appl. Nano Mater. .... Graduate School of the Chinese Academy of Sciences, Beijing .... Structures of Metal–Organic Fr...
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Solvent-Dependent Formation of Cd(II) Coordination Polymers Based on a C2-Symmetric Tricarboxylate Linker Lina Li,†,∥ Shuyun Wang,†,∥ Tianliang Chen,†,∥ Zhihua Sun,† Junhua Luo,*,†,‡ and Maochun Hong†,‡ †

Key Laboratory of Optoelectronic Materials Chemistry and Physics, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China ‡ State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China ∥ Graduate School of the Chinese Academy of Sciences, Beijing 100039, China S Supporting Information *

ABSTRACT: Three novel solvent-dependent Cd(II) coordination architectures [Cd3(BPT)2(DMF)2]·2H2O [1], [Cd3(BPT) 2 (DMA) 2 ] [2], and [(CH 3 CH 2 ) 2 NH 2 ]·[Cd(BPT)]·2H2O [3] were obtained by the hydrothermal reaction of a C2-symmetric tricarboxylate linker, biphenyl-3,4′,5-tricarboxylic acid (H3BPT), with cadmium nitrate in the mixed solvents of water with N,N-dimethylformamide (DMF), N,Ndimethylacetamide (DMA), diethylformamide (DEF), respectively. Single-crystal X-ray diffraction analyses reveal that complex 1 is a three-dimensional (3D) network containing infinite Cd−O−Cd chains with the solvent DMF molecule bridging the neighboring Cd1 and Cd2 centers. Though complex 2 also has a 3D network containing infinite metal-carboxylate chains, the solvent DMA molecule only coordinates to one of the Cd(II) centers as a terminated solvent molecule. Complex 3 possesses a two-dimensional (2D) (6, 3) honeycomb type net formed by the mononuclear metal ion and the BPT ligand, which are further stacked in ABAB fashion through π−π interactions into a 3D supramolecular architecture. The effect of solvents on the formation of the coordination networks has been shown in the three compounds obtained, and the distinction of coordination architectures is due to the coordination abilities of solvent molecules with the metal centers. The structure stabilities and photoluminescent properties of the three coordination polymers have also been investigated.

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differences in atomic connectivity or network catenation.8 Solvent as one of the important factors often directly or indirectly influences the coordination behavior of the metal ions: it participates in the coordinated reactions or influences the overall frameworks without participating in coordination.9 H3BPT as a C2-symmetric tricarboxylate ligand has been used to prepare functional MOFs with intriguing structures and properties,10 and a 3D polar nanotubular coordination polymer and a novel independent one-dimensional (1D) coordination polymer nanotube based on this linker have been synthesized in our previous work.11 In order to further study such C2symmetric tricarboxylate ligand based coordination polymers and investigate the influence of solvent on the coordination connectivity and related network, we designed the reactions of H3BPT ligand with Cd(II) salt in congener but three different solvents. The fine distinctions of solvents led to three entirely

INTRODUCTION The rational design and assembly of metal−organic frameworks (MOFs) have attracted much more attention in past few decades owing to their intriguing topologies and crystal packing motifs1 as well as potential applications in gas adsorption, sensors, photoactive materials, ion exchange, and so on.2 Crystal engineering affords us a powerful tool for the design and construction of coordination frameworks.3 But as the saying goes “The peasant who wants to harvest in his lifetime cannot wait for the ab initio theory of weather”,4 great efforts have been taken by many researchers and numerous metal− organic frameworks with unique structures and properties have been designed and synthesized by utilizing the tool.5 Generally, it is viable to select appropriate metal centers and organic linkers to form networks with predetermined structures and desired properties.6 However, in real chemical reactions, the environments, such as pH value, solvent, temperature, and reagent concentration, have an unpredictable impact on the crystallization of MOFs.7 Minor changes of such environmental factors may lead to different architectures originated from © 2012 American Chemical Society

Received: May 7, 2012 Revised: June 23, 2012 Published: July 3, 2012 4109

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Table 1. Crystal Data and Structure Refinements for Compounds 1−3 empirical formula formula weight temperature (K) wavelength (Å) crystal system space group a (Å) b (Å) c (Å) α/deg β/deg γ/deg volume (A3) Z calcd density (g/cm3) abs coeff (mm−1) F(000) crystal size (mm) reflns collected/ unique R(int) goodness-of-fit R1 (on Fo2, I > 2σ(I))a wR2 (on Fo2, I > 2σ(I))a a

Table 2. Selected Bond Lengths [Å] and Angles [deg] for Compounds 1−3a

1

2

3

C36H32Cd3N2O16 1085.87 293(2) 0.71073 triclinic P1̅ 7.8733(1) 10.1432(1) 13.528 68.355(12) 79.645(16) 70.702(14) 945.696(15) 1 1.907

C38H32Cd3N2O14 1077.86 293(2) 0.71073 monoclinic C2/c 19.9999(17) 10.0714(6) 18.9240(17) 90 101.196(6) 90 3742.8(5) 4 1.913

C19H17Cd1N1O8 499.75 293(2) 0.71073 monoclinic P21/c 13.5962(13) 18.848(2) 7.7377(8) 90 96.832(9) 90 1968.2(4) 4 1.684

1.748 534 0.20 × 0.12 × 0.10 7116/3170

1.762 2120 0.20 × 0.10 × 0.05 14211/4281

1.156 1680 0.30 × 0.15 × 0.10 16659/4465

0.0336 1.210 0.0668

0.0429 1.055 0.0523

0.0678 1.094 0.0631

0.1735

0.1453

0.1867

1 Cd(1)−O(6D) Cd(1)−O(4A) Cd(1)−O(3B) Cd(1)−O(1) Cd(1)−O(2) O(6D)−Cd(1)−O(4A) O(6D)−Cd(1)−O(3B) O(4A)−Cd(1)−O(3B) O(6D)−Cd(1)−O(1) O(4A)−Cd(1)−O(1) O(3B)−Cd(1)−O(1) O(6D)−Cd(1)−O(2) O(4A)−Cd(1)−O(2) O(1)−Cd(1)−O(2) O(6D)−Cd(1)−O(7C)

Cd(1)−O(7C) Cd(2)−O(2) Cd(2)−O(5F) Cd(2)−O(7C) O(4A)−Cd(1)−O(7C) O(3B)−Cd(1)−O(7C) O(1)−Cd(1)−O(7C) O(2)−Cd(1)−O(7C) O(1)−Cd(1)−O(3A) O(2)−Cd(1)−O(3A) O(5F)−Cd(2)−O(2) O(5F)−Cd(2)−O(7C) O(2)−Cd(2)−O(7C)

2.481(10) 2.313(8) 2.170(8) 2.346(8) 84.1(3) 169.6(3) 89.3(3) 77.6(3) 130.8(3) 172.6(3) 90.8(3) 87.5(3) 82.3(3)

2

R1 = Σ∥Fo| − |Fc∥/Σ|Fo|, wR2 = [Σ(|Fo| − |Fc| )/Σ|Fo| ] . 2

2

2 1/2

different coordination architectures. Herein we report the syntheses, crystal structures, and luminescent properties of the three novel solvent-dependent Cd(II) coordination polymers.

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2.234(8) 2.246(8) 2.269(9) 2.381(9) 2.408(7) 130.0(3) 84.4(3) 105.8(3) 145.0(3) 84.0(3) 94.6(3) 91.3(3) 133.7(3) 53.9(3) 86.8(3)

Cd(1)−O(7A) Cd(1)−O(4B) Cd(1)−O(5C) Cd(1)−O(3) Cd(1)−O(2)

2.177(4) 2.233(4) 2.278(4) 2.332(5) 2.371(4)

Cd(1)−O(5B) Cd(2)−O(6A) Cd(2)−O(1D) Cd(2)−O(2) O(5)C−Cd(1)− O(2) O(3)−Cd(1)−O(2)

2.639(5) 2.226(4) 2.271(5) 2.333(5) 129.6(2)

O(7A)−Cd(1)− O(4B) O(7A)−Cd(1)− O(5C) O(4B)−Cd(1)− O(5C) O(7A)−Cd(1)−O(3)

127.99(18)

O(4B)−Cd(1)− O(2) O(6A)−Cd(2)O(1D) O(6A)−Cd(2)− O(2) O(1D)−Cd(2)− O(2)

104.73(19)

O(4B)−Cd(1)−O(3)

91.2(2)

O(5C)−Cd(1)−O(3) O(7A)−Cd(1)−O(2)

89.19(17) 100.27(17)

Cd(1)−O(4A) Cd(1)−O(5B) Cd(1)−O(1) Cd(1)−O(7) O(4A)−Cd(1)− O(5B) O(4A)−Cd(1)−O(1) O(5B)−Cd(1)−O(1) O(4A)−Cd(1)−O(7) O(5B)−Cd(1)−O(7) O(1)−Cd(1)−O(7) O(4A)−Cd(1)−O(8)

2.241(5) 2.310(5) 2.372(6) 2.377(5) 170.15(19)

Cd(1)−O(8) Cd(1)−O(2) Cd(1)−O(6B) O(2)−Cd(1)−O(6B) O(7)−Cd(1)−O(8)

2.376(5) 2.501(6) 2.562(5) 150.2(2) 153.45(18)

105.6(2) 83.31(19) 83.52(19) 94.1(2) 80.94(18) 94.8(2)

O(4A)−Cd(1)−O(2) O(5B)−Cd(1)−O(2) O(1)−Cd(1)−O(2) O(7)−Cd(1)−O(2) O(8)−Cd(1)−O(2) O(4A)−Cd(1)− O(6B) O(5B)−Cd(1)− O(6B) O(1)−Cd(1)−O(6B) O(8)−Cd(1)−O(6B)

84.46(19) 104.5(2) 53.0(2) 126.5(2) 79.4(2) 116.85(18)

O(5B)−Cd(1)−O(8)

83.1(2)

O(1)−Cd(1)−O(8) O(7)−Cd(1)−O(6B)

124.59(18) 78.87(18)

86.23(16) 109.89(16) 139.58(19)

54.24(17)

87.75(17) 86.22(19) 83.8(2)

3

EXPERIMENTAL SECTION

Materials and Methods. All the solvents and reagents were of analytical grade and used as received without further purification. Elemental analyses were determined on an Elemental vario EL III analyzer. The FT-IR spectra were measured as KBr pellets on a Nicolet Magna 750 FT-IR spectrometer in the range of 4000−400 cm−1. Powder X-ray diffraction (PXRD) patterns were collected in the 2θ range of 5−40° with a scan step of 0.05° in a sealed glass capillary on a Rigaku MiniFlex diffractometer. The fluorescence measurements were performed on an Edinbergh Analytical instrument FLS920. Thermogravimetric analyses (TGA) were performed on a Netzsch STA 449C thermal analyzer from room temperature to 800 °C under nitrogen atmosphere at a heating rate of 10 °C/min. Synthesis of 1. A mixture of H3BPT (0.04 mmol, 11.4 mg) and Cd(NO3)2·4H2O (0.06 mmol, 18.5 mg) was dissolved in 6 mL of DMF/H2O (2:1) in a 20 mL vial, and then an aqueous solution of HClO4 (40 μL, 1 M) was added. The resulting solution was heated for 3 days at 90 °C. The product was obtained as crystalline material (yield 48% based on Cd) by filtration and washed with ethanol. Anal. Calcd for C36H32Cd3N2O16: C, 39.81; H, 2.97; N, 2.58%. Found: C, 39.78; H, 2.99; N, 2.61%. IR (cm−1): 3480(m, br), 2926(w), 1650(m), 1605(m), 1555(vs), 1440(m), 1395(s), 1285(w), 1114(w), 1068(w), 1014(w), 940(w), 862(w), 775(w), 734(w), 668(w). Synthesis of 2. The preparation of 2 was similar to that of 1, except DMA was used instead of DMF. Colorless stick crystals of 2 were obtained after filtration, washed with ethanol, and dried in air. The yield was 52% based on Cd. Anal. Calcd for C38H32Cd3N2O14: C, 42.38; H, 2.99; N, 2.60%. Found: C, 42.26; H, 3.02; N, 2.59%. IR (cm−1): 2933(w), 1609(m), 1565(vs), 1544(vs), 1524(vs), 1436(m),

53.31(16) 129.93(18) 78.35(17)

a Symmetry transformations used to generate equivalent atoms. For 1: A, x, y + 1, z; B, −x, −y + 2, −z + 1; C, −x + 1, −y + 2, −z + 1; D, x, y, z + 1; E, −x, −y + 3, −z + 1; F, −x + 1, −y + 2, −z. For 2: A, x − 1/2, −y + 3/2, z − 1/2; B, x − 1/2, −y + 1/2, z − 1/2; C, −x + 1/2, y + 1/2, −z + 1/2; D, −x + 1/2, −y + 3/2, −z. For 3: A, −x + 2, y − 1/2, −z + 3/2; B, x − 1, y, z.

1396(s), 1364(s), 1296(w), 1112(w), 1031(w), 855(w), 775(w), 726(w), 608(w). 4110

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Figure 1. (a) The coordination environments of the Cd(II) ions; (b) the metal chain linked by BPT ligands and DMF molecules; (c) the viewing of 2D layer network formed by the metal chain and BPT ligands; (d) the 3D polyhedral open-framework along the a axis. Synthesis of 3. The preparation of 3 was also similar to that of 1, except DMF was replaced by DEF. Colorless plate crystals of 3 were obtained after filtration, washed with ethanol, and dried in air. The yield was 40% based on Cd. Anal. Calcd for C19H23Cd1N1O8: C, 45.11; H, 4.58; N, 2.77%. Found: C, 44.48; H, 4.18; N, 2.58%. IR (cm−1): 3420(m, br), 3140(m), 2992(w), 2878(w), 1620(w), 1572(m), 1541(vs), 1390(s), 1364(s), 1291(w), 1186(w), 1112(w), 1059(w), 918(w), 870(w), 848(m), 769(w), 733(w), 682(w), 633(w), 564(w), 540(w). Single Crystal Structure Determination. Suitable single crystals of compounds 1−3 were carefully selected under an optical microscope and glued to thin glass fibers. The intensity data were collected on a Rigaku Mercury CCD diffractometer for compounds 1−3. The CrystalClear software12 was used for data reduction and empirical absorption correction. All the structures were solved by the direct methods and refined by the full-matrix least-squares method on F2 using SHELXS-97 and SHELXL-97.13 All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms attached to their parent atoms of organic ligands were geometrically placed and refined using a riding model. Crystal data as well as details of data collection and refinement for compounds 1−3 are summarized in Table 1, and selected bond lengths and angles are given in Table 2.

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the metal ion. The results indicate that the solvents play an important role in determining the architectures of the final products. The three complexes were characterized by IR spectroscopy, TG analyses, elemental analyses, and single-crystal X-ray diffraction analyses. The results of TG analyses and elemental analyses reveal that the components of the three complexes are in agreement with their formulas from single crystal structures. IR spectral shapes of the three complexes are slightly different (Figure S1, Supporting Information). For complex 1, the characteristic bands at 1650 and 1395 cm−1 should be assigned to the asymmetric vibration and symmetric stretching vibration of the carboxylate groups, respectively. For complexes 2 and 3, the peaks of asymmetric vibration and symmetric stretching vibration of the carboxylate groups are at 1609 and 1396 cm−1, and 1620 and 1390 cm−1, respectively. In the above three complexes, the stretching bands of carboxyl groups shift to lower frequencies compared to that of the carboxyl group of free H3BPT ligand with the characteristic peak at ca.1700 cm−1,14 which is consistent with the X-ray structural analytical results. The value of Δν(νas(COO) − νs(COO)) suggests that the carboxylate groups in the three compounds are involved in the coordination to the metal ions.15 Structural Descriptions. Structural Description of 1, [Cd3(BPT)2(DMF)2]·2H2O. Complex 1 crystallizes in triclinic P1̅ space group and the asymmetric unit contains one and a half Cd(II) centers, one BPT linker, one coordinated DMF molecule, and one guest water molecule. As illustrated in Figure 1a, the Cd1 atom is seven-coordinated by six carboxylate oxygen atoms (O1, O2, O3A, O3B, O4A, O6) from four BPT ligands (Cd−O distances range from 2.234 (8) to 2.408 (7) Å) and

RESULTS AND DISCUSSION

Synthesis and Characterization. Complexes 1, 2, and 3 have been successfully synthesized under hydrothermal conditions with the same reactants but in different mixed solvents. For 1 and 2, the solvents influence the coordination architectures via directly coordinating to the metal ions in different ways: as a bridging linker in 1 and terminal solvent molecule in 2. For 3, the DEF solvent molecule was decomposed and only affects indirectly the overall framework without coordinating to 4111

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Figure 2. (a) The coordination environments of the Cd12+ and Cd22+ cations; (b) the metal chain linked by BPT linkers with DMA molecules as the hands extending outside; (c) the viewing of 2D layer network formed by the metal chain and BPT ligands; (d) the 3D polyhedral framework assembled by the metal layers and BPT pillars viewed along the a axis.

one DMF oxygen atom (O7C) with a Cd−O distance of 2.481 (10) Å to generate a pentagonal biyramid coordination geometry. Different from Cd1, the Cd2 atom has a octahedral geometry with four carboxylate oxygen atoms (O2, O2C, O5D, O5F) provided by four different BPT ligands (Cd−O distances range from 2.170 (8) to 2.313 (8) Å) and two oxygen atoms (O7, O7C) from two coordinated DMF molecules (Cd−O 2.346 (8) Å). The Cd1 and Cd2 centers are bridged by two BPT carboxylate groups (O2, O5D) and one DMF (O7C) molecule to form an infinite Cd−O−Cd rod (Figure 1b). The Cd−O−Cd rods are bridged by the BPT linkers to form a 2D layer network (Figure 1c). The BPT ligand has three flexible carboxylic binding sites, so it extents forward and backward to link the adjacent layers to give rise to a 3D staggered ladder-like framework (Figure 1d) with guest H2O molecules occupying the channels. Moreover, the guest H2O molecules form strong hydrogen bonds with the adjacent carboxyl O atoms (O8− H8A···O1, 2.910 Å, 135°). Structural Description of 2, [Cd3(BPT)2(DMA)2]. Singlecrystal X-ray diffraction analyses reveal that complex 2 crystallizes in monoclinic C2/c space group. The asymmetric unit contains one and a half Cd(II) centers, one BPT ligand, and one coordinated DMA molecule. As illustrated in Figure 1a, the Cd1 atom is six-coordinated by six carboxylate oxygen atoms (O2, O3, O4B, O5B, O5C, O7A) from four BPT ligands (Cd− O distances range from 2.177 (4) to 2.639 (5) Å) to generate a distorted octahedral coordination geometry. The Cd2 atom has a octahedral geometry with four carboxylate oxygen atoms (O2, O2D, O6A, O6E) provided by four different BPT ligands (Cd−O distances range from 2.226 (4) to 2.333 (5) Å) and

two oxygen atoms (O1, O1D) from two terminated coordinated DMA molecules (Cd−O 2.271 (5) Å). The three carboxylate groups of the BPT ligand show three coordination modes that coordinate to the Cd2+ respectively in complex 2: one is in chelating mode, another in bridging mode, and the third one in chelating/bridging mode. The Cd1 and Cd2 centers are linked by two kinds of bridges (O2; O6A−C−O7A) to give rise to metal carboxylate chains with the terminal DMA molecules as the hands extending outside (Figure 1b). The metal carboxylate chains are bridged by BPT linkers to form a 2D layer network (Figure 1c), and the remaining carboxylic binding sites of BPT ligands extend downward and upward to link the adjacent layers to give rise to a 3D framework (Figure 1d). Structural Description of 3, [(CH 3 CH 2 ) 2 NH 2 ]·[Cd(BPT)]·2H2O. Single-crystal X-ray diffraction analyses reveal that complex 3 crystallizes in monoclinic P21/c space group. The asymmetric unit of 3 contains one Cd(II) center, one BPT ligand, two coordinated H2O molecules, and one protonated diethylamine cation. Here the protonated diethylamine cation which resolved from DEF solvent makes the complex achieve charge neutrality. As illustrated in Figure 1a, the Cd1 atom is seven-coordinated by five carboxylate oxygen atoms (O1 to O6) from three BPT ligands (Cd−O distances range from 2.241 (5) to 2.562 (5) Å) and two oxygen atoms (O7, O8) of two coordinated H2O molecules (Cd−O distances are 2.377 (5) and 2.376 (5) Å) to give birth to a pentagonal bipyramid coordination geometry. In 3, the BPT ligand has one coordination mode to coordinate with Cd2+ cations through five carboxyl oxygen atoms, in which two carboxyl groups both 4112

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Figure 3. (a) The coordination environments of the Cd(II) ion; (b) the coordination mode of BPT ligand; (c) the 2D reticular framework viewed down the c direction; (d) the 3D topology in ABAB packing fashion.

adopt a chelating coordination mode and the third one in a bridging coordination mode (Figure 3b). The bond angles of O1−Cd1−O2 and O5−Cd1−O6 are 53.0 (2) and 53.31 (16)°, respectively. Interestingly, the Cd2+ ions are bridged by three BPT to adjacent Cd2+ ions and each BPT ligand links with three Cd2+ ions to afford a mononuclear reticular structure. So, the Cd2+ ions can be considered as 3-connected nodes and are linked by three 3-coordinated BPT linkers to form a (6, 3) honeycomb type net (Figure 3c). Further, the 2D network stack in ABAB fashion into a 3D supramolecular architecture (Figure 3d). It is noteworthy that there are two types of molecular interactions between the adjacent layers: the weak π−π interactions between the adjacent benzene ring planes of BPT ligands with d = 3.8844 (Å), θ = 8.924° (d stands for the centroid−centroid distance, θ is the dihedral angle between two benzene ring planes) and the hydrogen band of oxygen atoms and benzene groups (C10−H10A···O4, 3.465 Å, 168°). Thermal Analysis and XRD Patterns. The thermogravimetric analysis and power X-ray diffraction of complexes 1−3 were carried out to investigate the thermal stability of frameworks as in Figures S2 and S3 of Supporting Information. Complex 1 shows a weight loss of about 3.0% from room temperature to 90 °C, which is attributed to the loss of the guest water molecules (expected 3.3%). No further weight loss was observed until 300 °C at which point the compound begins to decompose. The PXRD patterns of 1 heated under different temperatures confirm that the host framework maintains stability upon solvent removal until decomposition. Compound

2 shows no weight loss at low temperature because it has no solvent molecules in the framework. The compound degrades at about 350 °C, and the PXRD patterns confirm the stability of the host framework. Complex 3 shows a weight loss of about 7.48% from room temperature to 92 °C, which is attributed to the loss of the guest water molecules (expected 7.12%). No further weight loss was observed until 300 °C at which the compound starts to decompose. The PXRD patterns of 3 also confirm that the host framework maintains stability upon solvent removal until decomposition. Luminescence Properties. We have also examined the photoluminescent properties of the three complexes in the solid state at room temperature (Figure 4). Complex 1 exhibits an intense violet emission at 383 nm upon being excited at 334 nm and complex 2 displays an intense emission peak at 376 nm upon being excited at 328 nm. Both have a slight blue-shift compared with that of pure H3BPT ligand with an emission of 395 nm, which indicates that the emission band of complexes 1 and 2 are due to the intraligand charge transfer (IL).16 Different from 1 and 2, the complex 3 excited at 332 nm produces an intense blue emission band with a maximum at 436 nm, and a weak emission band with a maximum at 385 nm is also observed. The red-shift emission of complex 3 may be assigned to the charge transition of the ligand-to-metal charge center (LMCT).17 Though we employed the same metal center and organic ligand to construct compounds 1−3, different solvents induced different coordination architectures and further affected their luminescent properties. The reason only complex 4113

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2010CB933501), and the One Hundred Talent Program of the Chinese Academy of Sciences.

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(1) (a) Wang, X. L.; Qin, C.; Wu, S. X.; Shao, K. Z.; Lan, Y. Q.; Wang, S.; Zhu, D. X.; Su, Z. M.; Wang, E. B. Angew. Chem., Int. Ed. 2009, 48, 5291. (b) Xuan, W. M.; Zhu, C. F.; Liu, Y.; Cui, Y. Chem. Soc. Rev. 2012, 41, 1677. (c) Schnobrich, J. K.; Cychosz, K. A.; Dailly, A.; Wong-Foy, A. G.; Lebel, O.; Matzger, A. J. J. Am. Chem. Soc. 2010, 133, 13941. (d) Su, C. Y.; Goforth, A. M.; Smith, M. D.; Pellechia, P. J.; Zur Loye, H. C. J. Am. Chem. Soc. 2004, 126, 3576. (2) (a) Yaghi, O. M.; O’Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705−714. (b) Zhou, H. C.; Long, J. R.; Yaghi, O. M. Chem. Rev. 2012, 112, 673. (c) Kitagawa, S.; Kitaura, R.; Noro, S. Angew. Chem., Int. Ed. 2004, 43, 2334. (d) Luo, T. T.; Wu, H. C.; Jao, Y. C.; Huang, S. M.; Tseng, T. W.; Wen, Y. W.; Lee, G. H.; Peng, S. M.; Lu, K. L. Angew. Chem. 2009, 121, 9625. (e) Wu, H. H.; Gong, Q. H.; Olson, D. H.; Li., J. Chem. Rev. 2012, 112, 836. (f) Lu, Z. Z.; Zhang, R.; Li, Y. Z.; Guo, Z. J.; Zhang, H. G. J. Am. Chem. Soc. 2011, 133, 4172. (g) Burd, S. D.; Ma, S. Q.; Perman, J. A.; Sikora, B. J.; Snurr, R. Q.; Thallapally, P. K.; Tian, J.; Wojtas, L.; Zaworotko, M. J. J. Am. Chem. Soc. 2012, 134, 3663. (3) (a) Eddaoudi, M.; Moler, D. B.; Li, H.; Chen, B.; Reineke, T. M.; O’Keeffe, M.; Yaghi, O. M. Acc. Chem. Res. 2001, 34, 319. (b) Abrahams, B. F.; Jackson, P. A.; Robson, R. Angew. Chem., Int. Ed. 1998, 37, 2656. (c) Zhou, Y. F.; Jiang, F. L.; Yuan, D. Q.; Wu, B. L.; Wang, R. H.; Lin, Z. L.; Hong, M. C. Angew. Chem., Int. Ed. 2004, 43, 5665. (d) Eddaoudi, M.; Kim, J.; Wachter, J. B.; Chae, H. K.; O’Keeffe, M.; Yaghi, O. M. J. Am. Chem. Soc. 2001, 123, 4368. (4) Von Schnering, H. G. Angew. Chem., Int. Ed. 1981, 20, 33. (5) (a) Yamada, T.; Kitagawa, H. Am. Chem. Soc 2009, 131, 6312. (b) Cui, Y.; Lee, S. J.; Lin, W. B. J. Am. Chem. Soc. 2003, 125, 6014. (c) Dietzel, P. D. C.; Morita, Y.; Blom, R.; Fjellvag, H. Angew. Chem., Int. Ed. 2005, 44, 6354. (d) Zhang, Z. J.; Zhang, L. P.; Wojtas, L.; Nugent, P.; Eddaoudi, M.; Zaworotko, M. J. J. Am. Chem. Soc. 2012, 134, 924. (6) (a) Dong, Y. B.; Jiang, Y. Y.; Li, J.; Ma, J. P.; Liu, F. L.; Tang, B.; Huang, R. Q.; Batten, S. R. J. Am. Chem. Soc. 2007, 129, 4520. (b) Zou, R. Q.; Zhong, R. Q.; Han, S. B.; Xu, H. W.; Burrell, A. K.; Henson, N.; Cape, J. L.; Hickmott, D. D.; Timofeeva, T. V.; Larson, T. E.; Zhao, Y. S. J. Am. Chem. Soc. 2010, 132, 17996. (c) Wang, Z. L.; Fang, W. H.; Yang, G. Y. Chem. Commun. 2010, 8216. (d) Wibowo, A. C.; Vaughn, S. A.; Smith, M. D.; Zur Loye, H. C. Inorg. Chem. 2010, 49, 11001. (e) Xie, L. X.; Hou, X. W.; Fan, Y. T.; Hou, H. W. Cryst. Growth Des. 2012, 12, 1528. (f) Liu, T. F.; Lu, J.; Tian, C. B.; Cao, M. N.; Lin, Z. J.; Cao, R. Inorg. Chem. 2011, 50, 2264. (7) (a) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629. (b) Tian, J.; Motkuri, R. K.; Thallapally, P. K.; McGrail, B. P. Cryst. Growth Des. 2010, 10, 5327. (c) Pachfule, P.; Das, R.; Poddar, P; Banerjee, R. Cryst. Growth Des. 2011, 11, 1215. (8) (a) Ma, L.; Lin, W. J. Am. Chem. Soc. 2008, 130, 13834. (b) Zhang, J. J.; Wojtas, L.; Larsen, R. W.; Eddaoudi, M.; Zaworotko, M. J. J. Am. Chem. Soc. 2009, 131, 17040. (c) Sun, D. F.; Ma, S. Q.; Simmons, J. M.; Li, J. R.; Yuan, D. Q.; Zhou, H. C. Chem. Commun. 2010, 1329. (d) Pan, L.; Frydel, T.; Sander, M. B.; Huang, X. Y.; Li, J. Inorg. Chem. 2001, 40, 1271. (e) Pedireddi, V. R.; Varughese, S. Inorg. Chem. 2004, 43, 450. (f) Wang, F. K.; Yang, S. Y.; Huang, R. B.; Zheng, L. S.; Batten, S. R. CrystEngComm 2008, 10, 1211. (g) Ma, L. F.; Wang, L. Y.; Lu, D. H.; Batten, S. R.; Wang, J. G. Cryst. Growth Des. 2009, 9, 1741. (9) (a) Banerjee, D.; Finkelstein, J.; Smirnov, A.; Forster, P. M.; Borkowski, L. A.; Teat, S. J.; Parise, J. B. Cryst. Growth Des. 2011, 11, 2572. (b) Chen, S. C.; Zhang, Z. H.; Huang, K. L.; Chen, Q.; He, M. Y.; Cui, A. J.; Li, C.; Liu, Q.; Du, M. Cryst. Growth Des. 2008, 8, 3437. (c) Huang, X. C.; Li, D.; Chen, X. M. CrystEngComm 2006, 8, 351. (10) (a) Guo, Z. R.; Li, G. H.; Zhou, L.; Su, S. Q.; Lei, Y. Q.; Dang, S.; Zhang, H. J. Inorg. Chem. 2009, 48, 8069. (b) Wong-Foy, A. G.; Lebel, O.; Matzger, A. J. J. Am. Chem. Soc. 2007, 129, 15740. (c) Schnobrich, J. K.; Cychosz, K. A.; Dailly, A.; Wong-Foy, A. G.;

Figure 4. Emisson spectra of complexes 1 (black), 2 (red), 3 (blue), and H3BPT (green) ligand in the solid state.

3 has charge transition of the ligand-to-metal center may because there are no infinite metal-carboxylate chains in the framework or coordination solvent molecules.

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CONCLUSION In summary, we have successfully constructed three novel solvent-induced Cd(II)-organic frameworks based on the C2-symmetric tricarboxylate linker under solvothermal conditions. Complexes 1 and 2 both have 3D coordination architectures based on infinite Cd−O−Cd chains, but the solvent DMF acts as a bridging linker in 1 and the solvent DMA as a terminated coordination solvent molecule in 2. Complex 3 shows a 2D (6, 3) honeycomb type net based on the mononuclear center and further assembled into a 3D supramolecular architecture through π−π interactions between the neighboring layers. We found that the change of solvent in the synthesis led to diverse coordination architectures, and distinct photoluminescent properties were also observed due to different solvent-dependent coordination structures of 1−3. This work highlights a delicate solventinduced assembly in crystal engineering of functional coordination polymers, which would lead to new compounds with interesting structures and properties.

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ASSOCIATED CONTENT

S Supporting Information *

X-ray crystallographic data in CIF format, TGA, IR, and PXRD patterns. This material is available free of charge via the Internet at http://pubs.acs.org.

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REFERENCES

AUTHOR INFORMATION

Corresponding Author

*Tel: +86-591-83730955. Fax: +86-591-83713005. E-mail: [email protected]. Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS This work was financially supported by the National Nature Science Foundation of China (21171166 and 51102231), the 973 key programs of the MOST (2011CB935904 and 4114

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Crystal Growth & Design

Article

Lebel, O.; Matzger, A. J. J. Am. Chem. Soc. 2010, 133, 13941. (d) Ji, C. C.; Li, J.; Li, Y. Z.; Guo, Z. G.; Zheng, H. G. CrystEngComm 2011, 13, 459. (e) Guo, Z. Y.; Xu, H.; Su, S. Q.; Cai, J. F.; Dang, S.; Xiang, S. C.; Qian, G. D.; Zhang, H. G.; O’Keeffe, M.; Chen, B. L. Chem. Commun. 2011, 5551. (f) Lin, Z. J.; Xu, B.; Liu, T. F.; Cao, M. N.; Lu, J.; Cao, R. Eur. J. Inorg. Chem. 2011, 3842. (11) (a) Li, L. N.; Ma, J. X.; Song, C.; Chen, T. L.; Sun, Z. H.; Wang, S. Y.; Luo, J. H.; Hong, M. C. Inorg. Chem. 2012, 51, 2438. (b) Li, L. N.; Luo, J. H.; Wang, S. Y.; Sun, Z. H.; Chen, T. L.; Hong, M. C. Cryst. Growth Des. 2011, 11, 3744. (12) Crystal Clear, Version 1. 36; Molecular Structure Corporation: The Woodlands, TX, and Rigaku Corporation: Tokyo, Japan, 2000. (13) Sheldrick, G. M. SHELXS 97, Program for Crystal Structure Solution; University of Göttingen: Göttingen, 1997. (14) Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4th ed.; John Wiley & Sons: New York, 1986. (15) Deacon, G. B.; Philips, R. J. Coord. Chem. Rev. 1980, 33, 227. (16) (a) Ren, Y. X.; Zheng, X. J.; Jin, L. P. CrystEngComm 2011, 13, 5915. (b) Huang, K. L.; Liu, X.; Chen, X.; Wang, D. Q. Cryst. Growth Des. 2009, 9, 1646. (c) Zhao, H.; Qu, Z. R.; Ye, H. Y.; Xiong, R. G. Chem. Soc. Rev. 2008, 37, 84. (17) (a) Liu, Y.; Karvtsov, V. Ch.; Larsen, R; Eddaoudi, M. Chem. Commun. 2006, 1488. (b) Lin, Z. Z.; Jiang, F. L.; Chen, L.; Yue, C. Y.; Yuan, D. Q.; Lan, A. J.; Hong, M. C. Cryst. Growth Des. 2007, 7, 1712.

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