Four Novel Coordination Polymers Based on a Flexible Zwitterionic

DOI: 10.1021/cg100885e

Four Novel Coordination Polymers Based on a Flexible Zwitterionic Ligand and Their Framework Dependent Luminescent Properties

2010, Vol. 10 4590–4595

Guo-Qiang Kong and Chuan-De Wu* Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China Received July 4, 2010; Revised Manuscript Received August 16, 2010

ABSTRACT: A new flexible bowl-shaped zwitterionic complex, 1,10 ,100 -(2,4,6-trimethylbenzene-1,3,5-triyl)tris(methylene)tris(4-carboxypyridinium) tribromide (H3LBr3) was designed and synthesized, which was subsequently used as an efficient ligand to construct four interesting coordination polymers of [Cu2Cl2L2(H2O)2] 3 Cl 3 Br 3 4H2O (1), [ZnLBr] 3 NO3 3 H2O (2), [Cd2L2Br2] 3 2NO3 3 4H2O (3), and [Cd2L2(Inic)(H2O)4(MeOH)2] 3 Br 3 2NO3 3 3H2O (Inic = isonicotinlate, 4) by reaction of L ligand with corresponding metal salts or in the presence of isonicotinic acid. In these coordination polymers, L ligands link up metal nodes to form distinct linear networks. Two bowl mouths of two L ligands surround each other to form a ball-shaped building synthon in compounds 1 and 4, while the linear networks in 2 and 3 are in cylinder-shaped configurations. The luminescent spectra of L and compounds 1, 2, 3, and 4 suggested that the potential field around L ligand should be an important factor on the fluorescent emissions. The successful construction of the four novel coordination polymers based on the flexible zwitterionic L ligand should provide valuable information for further generation of novel topological networks with interesting properties.

Introduction Numerous studies on metal-organic coordination polymers have achieved great progress for the construction of various interesting topological architectures and for applications in diverse fields of catalysis,1 gas storage,2 luminescence,3 magnetism,4 electrical conductivity,5 nonlinear optics,6 and molecular sensors.7 It has been observed that organic ligands played crucial roles for the designed synthesis of some interesting coordination networks, such as the donating type, the flexibility, and the geometry of the organic ligands.8 Recent elaborations have proved that the rigid aromatic multicarboxylates, such as benzene-1,3,5-tricarboxylate, terephthalate, and benzene-1,2,4,5-tetracarboxylate, are effective ligands to bridge metal nodes into a variety of interesting open metal-organic networks with various cavity dimensions and shapes for potential applications.9 In contrast to rigid carboxylates, the coordination networks constructed from flexible carboxylates are relatively underdeveloped.10 It is difficult to predict either the composition or the network topology constructed from a flexible carboxylate due to the conformational freedom in the assembly process. However, the special conformation and coordination functionality of the flexible ligand might generate some unprecedented coordination frameworks. Zwitterionic complexes have attracted considerable interest, because they can function as ionic liquid precursors or ionic liquids for potential applications as cleaner and green and environmentally friendly reaction media in organic processes.11 However, there are only a few examples of zwitterionic ligand functionalized coordination polymers.12 In order to understand the coordination chemistry of flexible ligands combined with zwitterionic functional groups and develop novel metalorganic polymers, we have designed and synthesized a flexible zwitterionic complex, 1,10 ,100 -(2,4,6-trimethylbenzene-1,3,5-triyl)tris(methylene)tris(4-carboxypyridinium) tribromide (H3LBr3). *Corresponding author. E-mail: [email protected]. pubs.acs.org/crystal

Published on Web 08/30/2010

Herein we report the syntheses, crystal structures, and characterizations of four interesting coordination polymers constructed from the new treble betaine derivative, [Cu2Cl2L2(H2O)2] 3 Cl 3 Br 3 4H2O (1), [ZnLBr] 3 NO3 3 H2O (2), [Cd2L2Br2] 3 2NO3 3 4H2O (3), and [Cd2L2(Inic)(H2O)4(MeOH)2] 3 Br 3 2NO3 3 3H2O (Inic = isonicotinate, 4). Experimental Section Materials and Measurements. All of the chemicals were obtained from commercial sources and were used without further purification, except ethyl isonicotinate and 1,3,5-tris(bromomethyl)-2,4,6trimethylbenzene were prepared according to the literature.13,14 1H NMR spectra were recorded on a 400 MHz spectrometer in D2O solution, and the chemical shifts were reported relative to TMS as internal standard (0 ppm). Elementary analyses were performed on a Vario MICRO element analyzer. IR spectra (KBr pellets) were taken on an AVATAR-370 Nicolet spectrometer in the 4000400 cm-1 region. Thermogravimetric analyses (TGA) were carried out on a Shimadzu simultaneous DTG-60A compositional analysis instrument from 30 to 920 °C under N2 atmosphere at a heating rate of 10 °C/min. Synthesis of L Ligand. The treble betaine ligand (L) was synthesized according to the route as shown in Scheme 1. A mixture of 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene (6.0 g, 15 mmol) and ethyl isonicotinate (6.8 g, 45 mmol) in 80 mL of CH3CN was refluxed for 3 days. After the mixture was cooled down to room temperature, the resulting precipitate was filtered, washed with CH3CN, and dried at 50 °C to give the ester of L. The resultant was dissolved in 15% HCl (w/w; 80 mL) and was subsequently refluxed for 6 h. The solvent was removed under reduced pressure to give a white power, which was recrystallized in H2O to afford colorless crystals (Yield: 74%). Anal. Calcd for L(%): H, 4.26; C, 44.80; N, 5.22. Found: H, 4.17; C, 45.11; N, 5.09. 1H NMR (400 MHz, CDCl3): δ = 2.26 (s, 9H), 6.10 (s, 6H), 8.35 (d, 6H), 8.81 (d, 6H). IR (KBr pellet, ν/cm-1): 1724(s), 1641(s), 1573(s), 1514(w), 1454(s), 1373(m), 1328(s), 1298(s), 1158(m), 1120(m), 1079(w), 1045(m), 874(w), 824(w), 764(m), 687(m), 520(w). Synthesis of 1. After H3LBr3 (0.016 g, 0.02 mmol) and CuCl2 3 2H2O (0.017 g, 0.1 mmol) were thoroughly dissolved in 5 mL of water, the pH value of the mixture was adjusted to 7 with 1.0 mol/L NaOH aqueous solution. The mixture was stirred at 80 °C for 1 h and was subsequently filtered. After 5 mL of EtOH was r 2010 American Chemical Society

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Scheme 1. Schematic Representation of the Synthesis Procedure of H3LBr3

Table 1. Crystal Data and Structure Refinements for Compounds 1, 2, 3, and 4 and La compound

L

1

C60H66Cu2N6O18BrCl3 chemical formula C30H34N3O8Br3 formula weight 804.33 1472.53 crystal system triclinic triclinic P1 space group P1 a (A˚) 11.2602(18) 11.886(2) b (A˚) 13.0082(17) 12.224(2) c (A˚) 13.297(2) 13.111(3) R (deg) 63.005(15) 66.65(3) β (deg) 65.037(17) 68.48(3) γ (deg) 74.537(13) 85.32(3) 3 ˚ 1566.5(4) 1622.5(6) V (A ) Z 2 1 1.705 1.507 Fcalcd (g 3 cm-3) 5.244 1.469 μ (mm-1) F(000) 808 756 data/parameters 4402/394 6345/397 0.1083 0.0561 Rint 1.053 0.999 GOF on F2 0.1209, 0.3363 0.0955, 0.2070 R1, wR2 [I > 2σ(I)] 0.2488, 0.3850 0.1245, 0.2299 R1, wR2 [all data] P P P P a R1 = (|Fo | - |Fc|)/ |Fo|, wR2 = [ [w(Fo2 - Fc2)2]/ w(Fo2)2]0.5.

added into the filtrate, blue crystals of 1 were formed after a few days (Yield: 30%). Anal. Cald for 1(%): H, 4.52; C, 48.94; N, 5.71. Found: H, 4.61; C, 49.61; N, 5.48. IR (KBr pellet, ν/cm-1): 1622(s), 1566(s), 1449(m), 1366(s), 1258(w), 1223(w), 1156(w), 1130(m), 1039(w), 881(w), 850(w), 823(w), 797(m), 776(m), 696(w), 676(w), 638(w), 540(w). Synthesis of 2. The pH value of a mixture of H3LBr3 (0.016 g, 0.02 mmol), Zn(NO3)2 3 6H2O (0.03 g, 0.1 mmol), 5 mL of water, and 5 mL of DMF was adjusted to 7 using 1.0 mol/L NaOH aqueous solution. Colorless crystals of 2 were formed after a few days (Yield: 50%). Anal. Calcd for 2(%): H, 3.89; C, 47.99; N, 7.46. Found: H, 3.77; C, 48.53; N, 7.49. IR (KBr pellet, ν/cm-1): 1641(s), 1569(s), 1458(m), 1364(s), 1232(w), 1208(w), 1156(w), 1129(m), 1042(w), 881(w), 860(w), 827(w), 797(w), 774(m), 696(m), 676(w), 662(w), 646(w), 557(w). Synthesis of 3. The synthesis procedure of 3 is similar to that for 2, except ZnNO3 3 6H2O was replaced by Cd(NO3)2 3 4H2O (Yield: 58%). Anal. Cald for 3(%): H, 3.83; C, 44.16; N, 6.87. Found: H, 3.91; C, 45.03; N, 6.53. IR (KBr pellet, ν/cm-1): 1629(s), 1566(s), 1455(m), 1383(s), 1240(w), 1205(w), 1157(w), 1127(m), 1046(w), 877(w), 829(w), 801(m), 774(m), 700(w), 680(w), 661(w), 541(w). Synthesis of 4. After H3LBr3 (0.016 g, 0.02 mmol) and isonicotinic acid (0.0012 g, 0.01 mmol) were thoroughly dissolved in 5 mL of water, the pH value of the mixture was adjusted to 7 with 1.0 mol/L NaOH aqueous solution. A solution of Cd(NO3)2 3 4H2O (0.03 g, 0.1 mmol) in 5 mL of MeOH was added under stirring. Colorless crystals of 4 were formed after a few days (Yield: 40%). Anal. Cald for 4(%): H, 4.50; C, 45.57; N, 7.03. Found: H, 4.61; C, 45.32; N, 6.83. IR (KBr pellet, ν/cm-1): 1626(s), 1565(s), 1452(m), 1381(s), 1157(w), 1127(m), 1043(w), 877(w), 828(w), 799(m), 774(m), 697(m), 638(w), 544(w). Single Crystal X-ray Data Collections and Structure Determinations. The unit cell determination and data collection for the crystal of L were performed on an Oxford Xcalibur Gemini Ultra diffractometer with an Atlas detector. The data were collected using graphite-monochromatic Cu radiation (λ=1.54178 A˚) at 293 K. The data sets were corrected by empirical absorption correction using spherical harmonics, implemented in the SCALE3 ABSPACK scaling algorithm.15 The determinations of the unit cells and data

2

3

4

C30H29ZnN4O10Br 750.85 monoclinic P21/c 14.6283(13) 15.3950(14) 15.2329(14) 90 115.038(2) 90 3108.1(5) 4 1.605 2.140 1528 5002/370 0.0469 1.199 0.0968, 0.2284 0.1187, 0.2382

C60H62Cd2N8O22Br2 1631.8 monoclinic P21/c 31.3519(11) 14.8394(7) 15.1860(4) 90 118.818(3) 90 6190.2(4) 4 1.751 2.065 3280 10071/739 0.0430 1.182 0.0974, 0.2551 0.1464, 0.2646

C68H80Cd2N9O29Br 1792.12 triclinic P1 14.538(5) 15.531(5) 16.492(5) 89.170(6) 84.707(6) 73.686(5) 3558(2) 2 1.673 1.254 1828 9560/855 0.0500 1.076 0.0981, 0.2457 0.1221, 0.2597

collections for the crystals of compounds 1, 2, 3, and 4 were performed on a Siemens SMART CCD APEX II. The data were collected using graphite-monochromatic Mo KR radiation (λ = 0.71073 A˚) at 293 K. The data sets were corrected by the SADABS program.16 The structures of all compounds were solved by direct methods and refined by full-matrix least-squares methods with the SHELX-97 program package.17 The SQUEEZE subroutine of the PLATON software suit was used to remove the scattering from the highly disordered guest molecules. The resulting new files were used to further refine the structures.18 H atoms on C atoms were generated geometrically. The data collection parameters, crystallographic data, and final agreement factors are collected in Table 1.

Results and Discussion The treble betaine ligand (L) was synthesized by reaction of 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene with ethyl isonicotinate in CH3CN and subsequent hydrolysis. Single crystal X-ray diffraction analysis has revealed that L crystallizes in the triclinic P1 space group. Three methylene-4-carboxylic acid groups of L orientate to the same side of the basic phenyl group, which results in a bowl-shaped configuration of L (Figure 1). The L ligands further interlink each other into a linear supramolecular network through strong hydrogen bondings between two neighboring carboxylate groups (O-H 3 3 3 O = 2.510 A˚), between the carboxyl oxygen atom and the water molecule (O-H 3 3 3 O = 2.506-2.612 A˚), and between the bromide atom and the water molecule (O-H 3 3 3 Br = 3.074-3.187 A˚). Moreover, the neighboring chains are hydrogen bonded between the carboxyl oxygen atom and the pyridine carbon atom (C-H 3 3 3 O = 3.175 A˚). It is interesting to note that L ligands are packed in pairs to form interesting supramolecular cages (Figure 2). The reaction of H3LBr3 and CuCl2 3 2H2O in a mixed solvent of water and EtOH afforded blue crystals of [Cu2Cl2L2(H2O)2] 3 Cl 3 Br 3 4H2O (1). Single crystal X-ray diffraction

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Figure 3. ORTEP representation of the symmetry expanded local structure for 1 (25% probability ellipsoids).

Figure 1. ORTEP representation of the crystal structure for H3L (25% probability ellipsoids).

Figure 2. View of the 3D supramolecular framework of L down the a axis.

analysis has revealed that compound 1 crystallizes in the triclinic P1 space group, which consists of 1D zigzag chains built from L ligands linking up square-plane coordinated copper(II) atoms (Figure 3). One of two symmetric independent CuII atoms coordinates to two carboxyl oxygen atoms of two L ligands (Cu-O = 1.928(4) A˚) and to two water molecules (Cu-O = 1.931(5) A˚) with O-Cu-O angles ranging from 88.2(2) to 91.8(2)°. The remaining CuII atom is linked by two carboxyl groups (Cu-O = 1.929(5) A˚) of two L ligands and two chloride atoms (Cu-Cl = 2.289(3) A˚) with O-Cu-Cl angles of 88.9(2)-91.1(2)°. Subsequently, each L ligand performs as a neutral bidentate ligand to join up two Cu atoms, which further propagate into an infinite zigzag chain with all Cu atoms in a straight line (Cu 3 3 3 Cu 3 3 3 Cu = 180°) (Figure 4). The neighboring zigzag chains are interlinked into a 2D wavelike lamellar network through strong hydrogen bondings between the uncoordinated carboxyl group and the aqua ligand with an O-H 3 3 3 O distance of 2.608 A˚. Subsequently, the neighboring lamellas are joined together through hydrogen bondings between the coordinated carboxylate group and the methyl group (C-H 3 3 3 O = 3.180-3.204 A˚) to form a 3D supramolecular architecture (Figure 5). Strikingly, the

mouths of two bowl-shaped L ligands of two chains surround each other to form an interesting supramolecular cage tightened by strong hydrogen bondings, with the average cage diameter of 8.26 A˚. TGA of 1 indicates that a weight loss of 7.2% occurred between 30 and 195 °C, corresponding to the loss of lattice water molecules and aqua ligands (expected 7.3%). The reaction of H3LBr3 and Zn(NO3)2 3 6H2O in a mixed solvent of water and DMF afforded colorless crystals of [ZnLBr] 3 NO3 3 H2O (2), which crystallizes in the monoclinic P21/c space group. Each ZnII atom coordinates to three monodentate carboxyl groups (Zn-O = 1.964(6)-1.977(6) A˚) of three L ligands and one bromide atom (Zn-Br = 2.299(2) A˚) in a slightly distorted tetrahedral geometry (Figure 6). Different from the coordination mode in 1, the three carboxylate groups of L ligand coordinate to three zinc atoms in 2. Subsequently, each L ligand links up three zinc metal centers, while each zinc atom is to coordinate to three L ligands to generate an interesting cylinder-shaped linear network (Figure 7). There are extensive hydrogen bonding interactions among the cylinder networks. The hydrogen bondings are between the carboxyl group and the pyridine carbon atom (C-H 3 3 3 O = 3.030-3.139 A˚) and between the carboxyl group and the methylene group (C-H 3 3 3 O = 3.214 A˚), which link the neighboring cylinders into an intervening thick lamellar network (∼10.87 A˚). The hydrogen bondings between the bromide atom and the carbon atom of pyridine (C-H 3 3 3 Br = 3.452 A˚) join the thick lamellar frameworks into a 3D supramolecular network structure. TGA of 2 indicates that a weight loss of 2.4% occurred between 30 and 135 °C, corresponding to the loss of lattice water molecules (expected 2.4%). When Zn(NO3)2 3 6H2O was replaced by Cd(NO3)2 3 4H2O in the synthesis procedure of 2, colorless crystals of [Cd2L2Br2] 3 2NO3 3 4H2O (3) were obtained after a few days. Single crystal X-ray diffraction analysis has revealed that compound 3 crystallizes in the monoclinic P21/c space group. Each CdII atom coordinates to three monodentate carboxyl groups (Cd-O = 2.136(11)-2.264(12) A˚) of three L ligands and one bromide atom (Cd-Br = 2.602(2)-2.653(4) A˚) in a slightly distorted tetrahedral geometry (Figure 8). The structural backbone of 3 is almost identical to that of 2. TGA of 3 indicates that a weight loss of 4.4% occurred between 30 and 147 °C, corresponding to the loss of lattice water molecules (expected 4.4%).

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Figure 4. View of the 1D zigzag chain in 1.

Figure 5. View of the 3D supramolecular framework of 1 down the a axis.

Figure 7. View of the linear framework (a) and the interdigitation of 1D chains (b and c) in 2.


The reaction of Cd(NO3)2 3 4H2O and H3LBr3 in the presence of HInic afforded colorless crystals of [Cd2L2(Inic)(H2O)4(MeOH)2] 3 Br 3 2NO3 3 3H2O (4). Single crystal X-ray diffraction analysis has revealed that compound 4 crystallizes in the triclinic P1 space group. As shown in Figure 9, there are two CdII atoms, two L, and one Inic in the asymmetric unit. Each CdII atom coordinates to two monodentate carboxylate groups (Cd-O = 2.264(9)-2.292(8) A˚) of two L ligands, two


water molecules (Cd-O = 2.281(9)-2.359(9) A˚), and one methanol molecule (Cd-O = 2.227(14)-2.400(8) A˚). The remaining octahedral coordination sites of Cd atoms are occupied by the carboxyl group (Cd-O = 2.310(12) A˚) or pyridine group (Cd-N = 2.356(11) A˚) of Inic. The linear backbone of L ligands linking up Cd atoms is similar to that in 1. The neighboring zigzag chains are subsequently jointed

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together by the bidentate Inic ligands to form 48-member macrocycles with the bowel mouths orienting to the opposite directions (Figure 10). The 1D frameworks are further stacked into a 3D supramolecular architecture by hydrogen bonding interactions between the water molecule and the uncoordinated carboxyl group (O-H 3 3 3 O = 2.624 A˚) and between the uncoordinated carboxyl group and the pyridine carbon atom of L ligand (C-H 3 3 3 O = 3.106 A˚), which comprise supramolecular cages as building synthons (Figure 11). TGA of 4 showed that a weight loss of 10.6% occurrs between 30 and 181 °C, corresponding to the loss of water and methanol molecules (expected 10.6%). The photoluminescent spectra of 1, 2, 3, 4, and L in the solid state at room temperature are shown in Figure 12. The emission spectrum of L ligand exhibits two broad emission bands at 417 and 463 nm upon excitation at 300 nm, which can be assigned to the ligand-centered electronic transition. The similar fluorescent emissions are also detected in the emission spectra of compounds 1, 2, 3, and 4. However, different degrees of red or blue shifts were observed around the band

of 417 nm, while the bands around 463 nm are almost immobilized. Thus, the emissions should be affected by the different environments around L ligand. Interestingly, an additional strong transition peak at 537 nm was observed only in compound 2, which may result from ligand-to-metal charge transfer.19 To investigate further whether there are more possible electron transitions, we have excited at 350 nm to measure the emission spectra for all compounds (Figure 13). Strikingly, broad peaks were obverted only in compounds 2 (545 nm) and 3 (536 nm). From the above crystal structure descriptions, we can see that these two compounds are built up


Figure 12. Solid luminescent spectra for compounds 1, 2, 3, and 4 and L ligand (λex = 300 nm).

Figure 10. View of the 1D framework of 4 built from 48-member macrocycle rings.

Figure 11. View of the 3D supramolecular framework of 4 built from supramolecular cages.

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Figure 13. Solid luminescent spectra for compounds 1, 2, 3, and 4 and L ligand (λex = 350 nm).

from cylinder-shaped chains, while compounds 1 and 4 and L ligand are constructed from bowl mouth surrounded balls. Consequently, we can conclude that the additional peaks in 2 and 3 contribute to the induction of the cylinder-shaped synthons, which can induce additional ligand-centered electron transitions. The slightly shifted emissions for compounds 2 and 3 should contribute to the different environments around L ligand. Conclusions In this work, we have designed and synthesized a new flexible zwitterionic L ligand, which presents an interesting bowl-shaped configuration for the generation of supracage or cylinder subunits. Four novel transition metal coordination polymers have been successfully obtained by reaction of L ligand with corresponding metal salts or in the presence of isonicotinic acid. This work showed the significant influences of the coordination patterns and the flexibilities of the zwitterionic ligand on the structural topologies, which offers valuable information for the rational designed synthesis of coordination networks. The luminescent property studies suggested that the potential field around L ligand is an important factor for the fluorescence emissions. This work illustrates that the utility of potential ionic liquid precursors as ligands lies in the rational design and synthesis of novel functional materials for potential applications. Acknowledgment. This work was supported by Zhejiang Provincial Natural Science Foundation of China (Grant No. R406209), Chinese Universities Scientific Fund (Grant No. 2010QNA3013), and the Specialized Research Fund for the Doctoral Program of Higher Education of China (Grant No. 20090101110017). Supporting Information Available: Additional figures and crystallographic data (CIF, PDF). This information is available free of charge via the Internet at http://pubs.acs.org.

References (1) (a) Wu, C.-D.; Hu, A.; Zhang, L.; Lin, W. J. Am. Chem. Soc. 2005, 127, 8940. (b) Fujita, M.; Kwon, Y. J.; Washizu, S.; Ogura, K. J. Am. Chem. Soc. 1994, 116, 1151. (c) Seo, J. S.; Whang, D.; Lee, H.; Jun, S. I.; Oh, J.; Jeon, Y. J.; Kim, K. Nature 2000, 404, 982. (d) Ohmori, O.; Fujita, M. Chem. Commun. 2004, 1586.

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(2) (a) Bastin, L.; Barcia, P. S.; Hurtado, E. J.; Silva, J. A. C.; Rodrigues, A. E.; Chen, B. J. Phys. Chem. C 2008, 112, 1575. (b) Hu, S.; Zhang, J.-P.; Li, H.-X.; Tong, M.-L.; Chen, X.-M.; Kitagawa, S. Cryst. Growth Des. 2007, 7, 2286. (c) Chen, B.; Ma, S.; Zapata, F.; Fronczek, F. R.; Lobkovsky, E. B.; Zhou, H.-C. Inorg. Chem. 2007, 46, 1233. (d) Kitagawa, S.; Kitaura, R.; Noro, S. Angew. Chem., Int. Ed. 2004, 43, 2334. (e) Thallapally, P. K.; Tian, J.; Kishan, M. R.; Fernandez, C. A.; Dalgarno, S. J.; McGrail, P. B.; Warren, J. E.; Atwood, J. L. J. Am. Chem. Soc. 2008, 130, 16842. (f) Mckinlay, R. M.; Thallapally, P. K.; Atwood, J. L. Chem. Commun. 2006, 2956. (g) Guo, Z.; Li, G.; Zhou, L.; Su, S.; Lei, Y.; Dang, S.; Zhang, H. Inorg. Chem. 2009, 48, 8069. (3) (a) Lu, W.-G.; Jiang, L.; Feng, X.-L.; Lu, T.-B. Inorg. Chem. 2009, 48, 6997. (b) White, K. A.; Chengelis, D. A.; Gogick, K. A.; Stehman, J.; Rosi, N. L.; Petoud, S. J. Am. Chem. Soc. 2009, 131, 18069. (c) He, J.; Yu, J.; Zhang, Y.; Pan, Q.; Xu, R. Inorg. Chem. 2005, 44, 9279. (d) Yue, Q.; Sun, Q.; Cheng, A.-L.; Gao, E.-Q. Cryst. Growth Des. 2010, 10, 44. (4) (a) Qian, J.; Yoshikawa, H.; Zhang, J.; Zhao, H.; Awaga, K.; Zhang, C. Cryst. Growth Des. 2009, 9, 5351. (b) Li, Z.; Zhu, G.; Guo, X.; Zhao, X.; Jin, Z.; Qiu, S. Inorg. Chem. 2007, 46, 5174. (c) Chen, P.-K.; Batten, S. R.; Qi, Y.; Zheng, J.-M. Cryst. Growth Des. 2009, 9, 2756. (d) Wang, R.; Zhang, J.; Li, L. Inorg. Chem. 2009, 48, 7194. (5) (a) Domenech, A.; Garcı´ a, H.; Domenech, M. T.; Llabres-iXamena, F. J. Phys. Chem. C 2007, 111, 13701. (b) Alvaro, M.; Carbonell, E.; Ferrer, B.; Llabres, i.; Xamena, F. X.; Garcia, H. Chem.; Eur. J. 2007, 13, 5106. (c) Kuc, A.; Enyashin, A.; Seifert, G. J. Phys. Chem. B 2007, 111, 8179. (6) (a) Myers, L. K.; Langhoff, C.; Thompson, M. E. J. Am. Chem. Soc. 1992, 114, 7560. (7) (a) Chen, B.; Wang, L.; Zapata, F.; Qian, G.; Lobkovsky, E. B. J. Am. Chem. Soc. 2008, 130, 6718. (b) Chen, B.; Wang, L.; Xiao, Y.; Fronczek, F. R.; Xue, M.; Cui, Y.; Qian, G. Angew. Chem., Int. Ed. 2009, 48, 500. (c) Achmann, S.; Hagen, G.; Kita, J.; Malkowsky, I. M.; Kiener, C.; Moos, R. Sensors 2009, 9, 1574. (8) (a) Bu, X.-H.; Chen, W.; Lu, S.-L.; Zhang, R.-H.; Liao, D.-Z.; Bu, W.-M.; Shionoya, M.; Brisse, F.; Ribas, J. Angew. Chem., Int. Ed. 2001, 40, 3201. (b) Dybtsev, D. N.; Chun, H.; Kim, K. Angew. Chem., Int. Ed. 2004, 43, 5033. (c) Wang, X.-L.; Qin, C.; Wang, E.-B.; Xu, L.; Su, Z.-M.; Hu, C.-W. Angew. Chem., Int. Ed. 2004, 43, 5036. (9) (a) Chae, H. K.; Siberio-Perez, D. Y.; Kim, J.; Go, Y.; Eddaoudi, M.; Matzger, A. J.; O’Keeffe, M.; Yaghi, O. M. Nature 2004, 427, 523. (b) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705. (c) Rosi, N. L.; Eckert, J.; Eddaoudi, M.; Vodak, D. T.; Kim, J.; O'Keeffe, M.; Yaghi, O. M. Science 2003, 300, 1127. (10) (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) Bar, A. K.; Chakrabarty, R.; Mukherjee, P. S. Inorg. Chem. 2009, 48, 10880. (c) Zhang, Z.-H.; Song, Y.; Okamura, T.-a.; Hasegawa, Y.; Sun, W.-Y.; Ueyama, N. Inorg. Chem. 2006, 45, 2896. (d) Liu, X.-G.; Wang, L.-Y.; Zhu, X.; Li, B.-L.; Zhang, Y. Cryst. Growth Des. 2009, 9, 3997. (e) Wang, S.-n.; Sun, R.; Wang, X.-s.; Li, Y.-z.; Pan, Y.; Bai, J.; Scheer, M.; You, X.-z. CrystEngComm 2007, 9, 1051. (11) (a) Welton, T. Chem. Rev. 1999, 99, 2071. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. (c) Sheldon, R. Chem. Commun. 2001, 2399. (d) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. (e) Huang, J.; Jiang, T.; Gao, H.; Han, B.; Liu, Z.; Wu, W.; Chang, Y.; Zhao, G. Angew. Chem., Int. Ed. 2004, 43, 1397. (f) Miao, W.; Chan, T. H. Acc. Chem. Res. 2006, 39, 897. (12) (a) Fei, Z.; Geldbach, T. J.; Zhao, D.; Dyson, P. J. Chem.;Eur. J. 2006, 12, 2122. (b) Reichert, W. M.; Holbrey, J. D.; Vigour, K. B.; Morgan, T. D.; Broker, G. A.; Rogers, R. D. Chem. Commun. 2006, 4767. (c) Fei, Z.; Zhao, D.; Geldbach, T. J.; Scopelliti, R.; Dyson, P. J.; Antonijevic, S.; Bodenhausen, G. Angew. Chem., Int. Ed. 2005, 44, 5720. (d) Fei, Z.; Geldbach, T. J.; Zhao, D.; Scopelliti, R.; Dyson, P. J. Inorg. Chem. 2005, 44, 5200. (13) Ferri, V.; Costa, E.; Biancardo, M.; Argazzi, R.; Bignozzi, C. A. Inorg. Chim. Acta 2007, 360, 1131. (14) (a) Zavada, J.; Pankova, M.; Holy, P.; Tichy, M. Synthesis 1994, 1132. (b) Armstrong, S. K.; Clunas, S.; Muir, K. W. Synthesis 1999, 993. (15) Oxford Diffraction Ltd. CrysAlisPro, Version 1.171.33.56; 2010. (16) Sheldrick, G. M. SADABS; Siemens Analytical X-ray Instrument Division: Madison, WI, 1995. (17) Sheldrick, G. M. Program for Structure Refinement; University of G€ottingen: Germany, 1997. (18) Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7. (19) (a) Allendorf, M. D.; Bauer, C. A.; Bhakta, R. K.; Houk, R. J. T. Chem. Soc. Rev. 2009, 38, 1330. (b) Sonoda, Y.; Goto, M.; Tsuzuki, S.; Tamaoki, N. J. Phys. Chem. A. 2006, 110, 13379. (c) Lewis, F. D.; Yang, J.-S. J. Phys. Chem. B 1997, 101, 1775.

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