Controllable Self-Assembly of Two Luminescent Silver(I) Metal

Article pubs.acs.org/crystal

Controllable Self-Assembly of Two Luminescent Silver(I) Metal− Organic Frameworks Bearing a Tetradentate Ligand Published as part of the Crystal Growth & Design virtual special issue IYCr 2014 - Celebrating the International Year of Crystallography Ling-Ling Mao,† Wei Liu,† Quan-Wen Li, Jian-Hua Jia,* and Ming-Liang Tong* MOE Key Lab of Bioinorganic and Synthetic Chemistry, State Key Laboratory of Optoelectronic Materials and Technologies, School of Chemistry & Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, P. R. China S Supporting Information *

ABSTRACT: Luminescent metal−organic frameworks (MOFs) are appealing. In this regard, the dye molecule 1,2,4,5-tetra(4pyridyl)benzene (bztpy), a tetradentate ligand, can be rationally incorporated for the modulation of structures and photochemical properties as a building unit. By reacting bztpy and K[Ag(CN)2] in the presence of CuCl in a solution of NH3· H2O/EtOH at room temperature, we managed to synthesize two novel MOFs exhibiting good luminescent behavior. In the reaction, CuCl was proven to be important as a catalyst, which enables the reactant to generate reactive intermediate [Ag(NH3)2] Cl with the help of ammonia. Thus, Ag+ ions released from intermediate promote the formation of products 1 and 2. Transformation between two compounds can be realized by simple operations. Topology studies reveal that 1 belongs to a 4-fold interpenetrating “moganite” net, but for 2 a new-found (3,4)-connected net occurred with a Schläfli symbol of {62.104}{62.10}2. Photoluminescent behaviors of solid 1 and 2 exhibit intense emission with λemmax at ca. 538 and 547 nm, respectively, mainly assigned to intraligand transition. On the basis of the facts above, the use of dye molecules into MOFs provides the way to modulate photochemical properties.

■

INTRODUCTION Metal−organic frameworks (MOFs)1 that employ metal− organic components as building blocks, where a rigid, multidentate organic bridge propagates the coordination geometry of metal node in three dimensions, have inspired molecular chemists for the past decades.2,3 They display widespread applications in lots of crucial realms, such as gas storage, separation, catalysis, magnetism, ferroelectricity, molecular recognition, biomedicine and optical materials, etc.4−8 Of particular interest are their attractive physicochemical properties due to the synergetic effect integrated from the subunits.9 For instance, luminescent properties of MOFs can be enhanced if organic linker molecules serve to absorb photon energies and transfer them to metal centers.10 Great effort has been made to design the MOFs in combination with specific structures and various photochemical traits by dealing with either the metal nodes or organic ligands.11,12 In this regard, © 2014 American Chemical Society

development of multitopic dye molecules as building units is one of the central tasks. A class of tetrapyridyl ligands have been recently investigated from the hydrothermal in situ metal/organic reaction of an unprecedented dehydrogenative coupling and/or hydroxylation of 1,3-bis(4-pyridyl)propane, resulting in 1,2,4,5-tetra(4pyridyl)benzene (bztpy) 10a,g,13,14 and 1a,4a-dihydroxyl1e,2e,4e,5e-tetra(4-pyridyl)cyclohexane (chtpy)14,15 ligands, respectively.16 Lots of effort has been put into the extension of these functional in situ ligands involved in MOFs with various metal ions, such as Co(II), Cu(I/II), Zn(II), and Cd(II).13−15 Lately, the bztpy ligand itself was found to exhibit diversification of luminescence in the solid state due to the Received: May 24, 2014 Revised: July 30, 2014 Published: August 7, 2014 4674

dx.doi.org/10.1021/cg500757a | Cryst. Growth Des. 2014, 14, 4674−4680

Crystal Growth & Design

Article

distinguished by the X-ray diffraction method, energy dispersive X-ray spectroscopy (EDXS) measurement was therefore conducted to study the composition of 1 (Figure S1, Supporting Information). The results reveal the absence of any copper atom in crystalline samples. Thus, the molecular formula can unambiguously be defined as [Ag2(μ4-bztpy){Ag(CN)2}2]·EtOH (1). The lattice ethanol molecule was defined by a combination of crystallographic data and TG-MS results, which are also in accordance with elemental microanalyses. Similar analyses for 2 confirmed its molecular formula as [Ag(μ3-bztpy){Ag(CN)2}] (2) (see Supporting Information for details). In order to understand the function of CuCl, workup without CuCl was carried out. Unfortunately, several attempts at the preparation of 1 failed. On the basis of these observations, we propose that the reaction generates a reactive intermediate [Ag(NH3)2]Cl by virtue of CuCl as the catalyst illustrated in Scheme 2a. The resulting [Ag(NH3)2]Cl reacts with K[Ag-

peculiar molecular packing and/or aqueous molecules in the lattice.10g We are especially interested in these kinds of dye-based materials,13d,14a,15a,c because their well-defined compositions and structures are helpful for elucidating a structure−property relationship. However, the process and mechanism of in situ reaction are usually ambiguous owing to the harsh hydrothermal condition. In view of the facts above, synthesis conducted in solution, as a conventional method, would provide direct insight into the reactive mechanism. To this end, we have initiated a strategy to organize isolated dye molecule bztpy with the linear complex K[Ag(CN)2] under mild conditions, leading to the formation of two Ag(I)−MOFs, [Ag2(μ4-bztpy){Ag(CN)2}2]·EtOH (1) and [Ag(μ3-bztpy){Ag(CN)2}] (2). Both are of noticeable luminescent behavior but with different topological nets. Complex 1 shows a 4-fold interpenetrating “moganite” net formed with the help of μ4bztpy ligands. For 2, however, a new topology was created in virtue of μ3-bztpy ligands. Furthermore, it is important for CuCl to act as a catalyst in reaction. We proposed that reactive intermediate [Ag(NH3)2]Cl is generated with the aid of CuCl and subsequently reacts with K[Ag(CN)2] and bztpy affording the desired products.

Scheme 2. Proposed Reactive Mechanism (a) and Conversion between 1 and 2 (b)

■

RESULTS AND DISCUSSION Synthesis and Characterization. The synthesis is outlined in Scheme 1. Different from the syntheses in hydro-/ Scheme 1. Schematic Diagram for 1 and 2

(CN)2] and bztpy ligands affording product 1 consequently. In this regard, the Ag+ of [Ag(NH3)2]+ seems very critical. So AgNO3 was added to replace CuCl to satisfy the Ag+ ions requirement. However, only 2 was obtained instead of 1. It was found that, in contrast with the molecular formula of 2, two silver(I) ions are present per molecule 1. Thus, more AgNO3 was employed so as to improve the proportion of Ag+ ions in solution. Finally, the reaction could hardly get 1. Instead, the resultant was proved to form compound Ag(bztpy)(NO3). This demonstrated the important role of CuCl in the preparation of 1. With the help of CuCl, more Ag+ ions can be released from K[Ag(CN)2] to satisfy the need of generating 1. Otherwise, the product will be prone to 2 because of a small amount of Ag+ ions in reaction. These facts also reveal the thermodynamic unstability of 1 in mother liquor (vide post). On the basis of the point of view above, in-depth insight into the mechanism of the generation of 1 was studied by directly conducting K[Ag(CN)2] and bztpy in solution of [Ag(NH3)2] Cl made from NH3·H2O and fresh AgCl. As expected, the product was proven to be 1 through single crystal X-ray diffraction measurement. Moreover, the reaction yield up to ∼85% also demonstrates the important role of [Ag(NH3)2]+ without catalysis of CuCl. This gives a better indication of the formation of intermediate [Ag(NH3)2]Cl during the synthesis of 1. Thermodynamic study shows that 1 would be transformed into 2 in mother liquor a few days later illustrated in Scheme 2b. This can be ascribed to extra bztpy ligands and ammonia in mother liquor. The transformation was found to be reversible. When crystalline samples 2 were placed in ethanol solution with the addition of both [Ag(NH3)2]Cl and K[Ag(CN)2],

solvothermal conditions comprising bztpy ligands, the preparation of 1 and 2 was conducted in mixed solvents (EtOH/H2O) accompanying by quantitative NH3·H2O at room temperature. Under this mild condition, control of the stoichiometric ratio between K[Ag(CN)2] and bztpy ligands isolated target products 1 and 2, respectively, in the presence of CuCl. The identities of 1 and 2 have been confirmed by IR spectroscopy, TG-MS measurements, and satisfactory elemental analyses. The IR spectra show a strong band at 2128 cm−1 for 1 and 2125 cm−1 for 2, typical of the ν(CN) stretching frequency. In consideration of the fact that metal ions cannot be 4675



Article

subsequent reaction of 2, [Ag(NH3)2]+ and [Ag(CN)2]− happened and generated product 1 after 1 week. Both of the transformations were confirmed by single crystal X-ray diffraction measurements. These results corroborate the thermodynamic unstability of 1 and provide the ways to control the conversion between 1 and 2. It deserves mention that 2 would be formed without the addition of CuCl. The silver(I) ions in molecule 2 were released slowly from reactant K[Ag(CN)2] with the help of NH3·H2O. The process could be accelerated by addition of AgNO3, resulting in an increase in the yield of 2. In addition, the importance of NH3·H2O was also verified. None of 1 would be obtained without of NH3·H2O in reaction, but only a few crystals of 2 could be observed after 2 weeks. This observation is in accord with the thermodynamic stability of 2 (vide supra). X-ray Crystal Structure. Single crystal X-ray diffraction measurements of 1 and 2 were carried out at 150 K. Relevant crystallographic parameters are listed in Table 1. Complex 1

The structure of 2 was found in monoclinic space group P21/ n with asymmetric unit containing one Ag(I) atom, one [Ag(CN)2]− unit and bztpy ligand. It is different from 1 that bztpy ligand of 2 links to metal ions in μ3- manner, with one nitrogen site vacant. Each μ3-bztpy ligand binds two AgN4 tetrahedra through Ag(I) atoms, of which four N donors are respective from two bztpy ligands and two [Ag(CN)2]− units (Figure 1d). Two crystallographically inequivalent Ag(I) sites occur in 2, that is four-coordinated site (Ag2) and threecoordinated site (Ag1) from [Ag(CN)2]− unit. Ag1 atoms are observed to connect with bztpy ligands in μ3-[Ag(CN)2]− coordination mode.18 Moreover, coordination of the Ag2 centers to [Ag(CN)2]− groups through terminal N atoms leads to formation of [Ag{Ag(CN)2}]∞ infinite chains (purple chains in Figure 1e), similar to polymer [(Cy3P)Ag(NCAgCN)]∞.19 These one-dimensional chains stack along the b axis and are linked in a unique way by the μ3-bztpy ligands creating an intricate 3D framework (Figure S4, Supporting Information). Topologically, the 3D network can be simplified by just considering the bztpy ligand and [{Ag(CN)2}(bztpy)] group as a three-connected node, respectively, and the tetrahedral Ag(I) center as a four-connected node, resulting in an infinite 3D (3,4)-connected 2-nodal net shown in Figure 1f. The Schläfli symbol for this net can be described as {62.104}{62.10}2, which represents a new topology by the TOPOS4.0 program.20 It is worth stressing that strong C−H····N complementary hydrogen bonds are formed between two bztpy ligands (Figure S5, Supporting Information), through the vacant N donors of pyridyl groups with neighboring hydrogen atoms (C−H····N, 2.445 Å). To some extent, the hydrogen-bonding interactions in 2 make a contribution to construct the complicated 3D framework. It was reported that the variety of the hydrogen bonds plays an essential role in controlling the complexity in both chemistry and biology.21 In addition, a pair of conformation isomers of bztpy, eclipsed and staggered, was separated in 1 and 2, respectively (Figure 2). The opposite two pyridyl rings of eclipsed isomer in 1 are absolutely eclipsed with the dihedral angles of 0°. And four nitrogen atoms of bztpy can shape a perfect plane. However, the staggered isomer found in 2 has two opposite pyridyl rings nearly perpendicular with a dihedral angle of 88.98°. The plane through four nitrogen atoms remains slightly bent (165.17°), which deviates from the idealized value of 180° observed in 1. A similar situation was reported in α- and β-Cd(II) complexes.13a The presence of eclipsed and staggered conformations in distinct compounds reveals the geometrical flexibility of bztpy ligands. This may be attributed to the fact that bztpy ligands exist in a μ4- and μ3-bridging manner in MOFs 1 and 2, respectively, induced by different topologies. Actually, bztpy ligands themselves also exhibit eclipsed or staggered conformation when cocrystallized with different solvents.14a Thermogravimetric Analysis and Powder X-ray Diffraction. The TGA curve of 1 (Figure S6, Supporting Information) exhibiting weight loss from 450 to 560 K is attributed to the loss of one lattice ethanol molecule (exp. 4.57%; calcd. 4.76%). The MS measurement around 525 K gives a more accurate result with peaks of ethanol (m/z = 46, 45, 31), which unambiguously verified the molecular formula of 1. For 2, TGA result indicates its excellent thermal stability because the compound was rarely decomposed under gradually heating until 560 K. The powder X-ray diffraction (PXRD) patterns for 1 and 2 are shown in Supporting Information (Figure S7). Phase purity

Table 1. Crystallographic Data for 1 and 2 formula Mr/g mol−1 crystal system space group a /Å b /Å c /Å α /° β /° γ /° V /Å3 Z ρc /g cm−3 F(000) reflns collected unique reflns Rint GOF on F2 R1a (I > 2σ(I)) wR2b (all data)

1

2

C32H24Ag4N8O 968.07 triclinic P1̅ 6.9753(5) 9.7052(10) 12.0656(10) 72.587(3) 88.593(2) 89.811(3) 779.13(12) 1 2.063 468.0 6989 3453 0.0562 1.067 0.0432 0.1081

C28H18Ag2N6 654.22 monoclinic P21/n 11.5405(3) 11.3638(3) 18.1067(4) 90.00 100.420(2) 90.00 2335.42(10) 4 1.861 1288.0 6451 3619 0.0326 1.022 0.0309 0.0744

a R 1 = ∑||F 0 | − |F c ||/∑|F 0 |. ∑[w(F02)2]}1/2.

b

wR 2 = {∑[w(F 0 2 − F c 2 ) 2 ]/

crystallizes in the triclinic space group P1̅. The asymmetric unit contains half of the formula unit, that is, one Ag(I) atom, two half [Ag(CN)2]− unit, half of a μ4-bztpy ligand and half lattice ethanol molecule. Three types of crystallographically inequivalent Ag(I) sites appear in 1, namely, one four-coordinated site (Ag1), and two linearly coordinated sites (Ag2, Ag3) from [Ag(CN)2]− building blocks (Figure 1a). Later two reside in slightly different environments when connecting to Ag1. As shown in Figures 1b and S2, μ4-bztpy ligands viewed as 4connected nodes are linked to tetrahedral Ag1 atoms, which extend to a 3D framework through a [Ag(CN)2]− linker. Thus, the 3D matrix can be easily constructed by joining these nodes together, forming a “moganite” interpenetrated net shown in Figure 1c. The Vvoid of 1 (without guest ethanol molecules, Figure S3, Supporting Information) is 11.6% as calculated by PLATON,17 confirming the accommodation of one guest ethanol per molecule. 4676



Article

Figure 1. Description of coordination environment for bztpy ligand and silver atoms in 1 (a) and 2 (d). Stick model of the 3D framework along the specified direction for 1 (b) and 2 (e). Topological presentation: “moganite” net for 1, μ4-Ag[Ag(CN2)2] and μ4-bztpy viewed as 4-connected nodes (c); (3,4)-connected net for 2, μ4-Ag(2) (green), μ3-Ag(1) (red), and μ3-bztpy (cyan) viewed as 4-, 3-, and 3-connected nodes, respectively; point symbol for 3D net: {62.104}{62.10}2 (f).

room temperature are shown in Figure 3. Excitation of 1 and 2 in the solid state at 471 and 479 nm produces strong luminescence with λemmax at ca. 538 and 547 nm, respectively. The emissive colors of two compounds can be captured by naked eyes under UV light, with an absolute quantum yield of 12% and 11% evaluated as the ratio of the emission photon number to the absorption photon number.22 The radiative lifetimes are found as the same order of magnitude as nanoseconds, determined to be 4.4 ns for 1 and 5.4 ns for 2 (Figure S9, Supporting Information). In comparison to

of the bulk samples was confirmed by nearly entire superposition of experimental PXRD patterns with that calculated from the single crystal study. Furthermore, PXRD data (Figure S7) of 1 synthesized directly from [Ag(NH3)2]Cl, KAg(CN)2, and bztpy in the absence of CuCl also give the agreement of simulated and experimental results, which confirms the importance of [Ag(NH3)2]Cl again. Photoluminescent Properties. In this report, we present the studies of the photoluminescent properties of 1 and 2. The excitation and emission maxima (named λexmax and λemmax) at 4677



Article

Ag+ ions released from intermediate promote the generation of products. In this regard, CuCl was proven to be important as a catalyst. Moreover, transformation between 1 and 2 can be realized by simple operations. Last but not least, intense luminescence for solid samples indicates the use of dye molecules in MOFs provides the way to modulate photochemical properties. In this way, plenty of other dye molecules have attracted our attention.

■

EXPERIMENTAL SECTION

Physical Measurements. The C, H, N microanalyses were performed with an Elementar Vario-ELCHNS elemental analyzer. The FT-IR spectra were recorded from KBr pellets in the range 4000−400 cm−1 with a Bruker-EQUINOX 55 FT-IR spectrometer. Powder X-ray diffraction (PXRD) intensities for polycrystalline samples were measured at room temperature on a Bruker D8 Advance diffratometer (Cu Kα, λ = 1.54056 Å) by scanning over the range 5−50° with a step of 0.2°/s. The calculated patterns were generated with Mercury. Thermogravimetric-differential thermal analysis (TG-DTA) coupled to mass spectrometer (STA449 F3 Jupiter-QMS 403C aedo) was used, and TG analysis was performed under the flowing N2 atm at a scan rate of 10 K min−1. Photoluminescence spectra including decay curves and absolute quantum yield were measured on an Edinburgh Instrument FLS920 combined fluorescence lifetime and steady state spectrometer. The steady-state luminescence was excited using unpolarized light from a 450 W xenon CW lamp at 298 K. The photoluminescence quantum yield was measured by using a 150 mm, BaSO4 coated integrating sphere set into the FLS920 sample chamber. The quantum yield was evaluated as the ratio of the emission photon number to absorption photon number. BaSO4 was conducted as the standard sample to record the number of photons which are not absorbed by the test sample.22 The existence of Ag/Cu and their ratio were determined by means of energy dispersive X-ray spectroscopy (EDXS) (S-520/INCA 300, Hitachi/Oxford, Japan) at room temperature. X-ray Crystallography and Data Collection. Diffraction intensities data of 1 were collected on a Rigaku R-AXIS SPIDER IP diffractometer using Mo Kα radiation (λ = 1.54056 Å) at 150(2) K, while the diffraction intensities data of 2 were collected on a Oxford Diffraction Gemini R CCD diffractometer with Cu Kα radiation (λ = 1.54178 Å). The structures were solved by direct methods, and all non-hydrogen atoms were refined anisotropically, through leastsquares on F2 using the SHELXTL program suite.25 Anisotropic thermal parameters were assigned to all non-hydrogen atoms. The hydrogen atoms of organic ligands were generated geometrically, while no attempt was made to locate hydrogen atoms of the disordered solvent molecules. The ORTEP plots and packing pictures were produced using Diamond 3.1.26 CCDC 1004958 (1) and 1004959 (2) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/data_request/cif. Materials and Synthesis. All of the reagents employed were commercially available and used without further purification. [Ag(NH3)2]Cl solution was prepared from the reaction of fresh AgCl and NH3·H2O. The bztpy ligand was prepared according to a literature method.10g [Ag2(μ4-bztpy){Ag(CN)2}2]·EtOH (1). Method A: K[Ag(CN)2] (80 mg, 0.4 mmol), CuCl (20 mg, 0.2 mmol), and bztpy (29 mg, 0.075 mmol) was dissolved in EtOH/H2O (9 mL, v:v = 8:1) under ultrasonication. Then the resulting mixture was added dropwise to NH3·H2O (0.1 mol/L, 1 mL) and stirred for 30 min. After that, the solution was filtered, and the filtrate was left for slow evaporation. Colorless rectangular crystals of 1 were obtained after several days in ∼20% yield based on bztpy. Method B: To a solution of [Ag(NH3)2]Cl (4 mL, 0.2 mmol), KAg(CN)2 (40 mg, 0.2 mmol), and bztpy (30 mg, 0.08 mmol) in ethanol (6 mL) were added. Then the resulting mixture was stirred for 5 h. After that, the solution was filtered, and the filtrate was slowly evaporated. Colorless

Figure 2. Eclipsed and staggered conformations of bztpy ligands in 1 and 2, respectively.

Figure 3. Excitation and emission spectra of 1 and 2 in the solid state recorded at room temperature.

luminescent spectra of free bztpy ligands, the emission peaks at ca. 540 nm mainly are assigned to intraligand transition, which are also exhibited by bztpy ligands (Figure S8, Supporting Information). The contribution of [Ag(CN)2]− was excluded because an insignificant signal of emission for solid K[Ag(CN)2] was observed at room temperature. Compared to free bztpy ligands, the slight wavelength shift of emission maxima may be caused by packing modes and/or rotation of pyridyl rings in eclipsed and staggered conformations when complicated MOFs were formed. Furthermore, for d10 system, it has been reported to possess intense photoluminescence produced or modified by metal−metal interactions, particularly in gold and silver complexes.23,24 Unfortunately, any kinds of Ag(I)··· Ag(I) interactions are not present in both 1 and 2. However, the differences of excitation profiles between free ligands and complexes indicate the possibility for dye molecules transferring photon energy to silver centers. With implication of results above, the conduct of dye ligands into MOFs provides the way to modulate photochemical properties.

■

CONCLUSION In this paper, we have made a successful attempt to synthesize two luminescent silver(I) MOFs involving dye molecules. The use of bztpy molecules and K[Ag(CN)2] in the presence of CuCl in NH3·H2O/EtOH at room temperature, led to the products of 1 and 2, which possess a “moganite” net and newfound (3,4)-connected net, respectively. The proposed mechanism for reaction reveals the formation of the reactive intermediate [Ag(NH3)2]Cl with the help of ammonia. Then 4678



Article

rectangular crystals of 1 were obtained after 1 week in ∼85% yield based on bztpy. Anal. Calcd (%) for C30H18N8Ag4·C2H5OH: C, 39.70; H, 2.50; N, 11.58. Found: C, 40.14; H, 2.68; N, 11.44. IR (KBr, cm−1): 3571m, 3418m, 3055w, 2960w, 2931w, 2128s, 1602s, 1478m, 1421s, 1220m, 828s, 704w. [Ag(μ3-bztpy){Ag(CN)2}] (2). Method A: The procedure was the same as that employed for complex 1, with the exception of K[Ag(CN)2] (40 mg, 0.2 mmol) in reaction. Pale yellow block-like crystals of 2 were obtained after several days in ∼30% yield based on bztpy. Method B: The procedure was the same as that employed for complex 1, except that K[Ag(CN)2] (60 mg, 0.3 mmol), AgNO3 (50 mg, 0.3 mmol), and bztpy (29 mg, 0.075 mmol) were conducted as reactants. Pale yellow block-like crystals of 2 were obtained after several days in ∼10% yield based on bztpy. Anal. Calcd (%) for C28H18N6Ag2: C, 51.40; H, 2.77; N, 12.85. Found: C, 51.01; H, 2.80; N, 12.73. IR (KBr, cm−1): 3073w, 3033m, 2993w, 2125s, 1595s, 1542m, 1469m, 1413s, 1381m, 1321w, 1218m, 1067m, 996m, 919m, 823m, 747w, 722w, 693m, 633m.

■

(h) Li, M.; Li, D.; O’Keeffe, M.; Yaghi, O. M. Chem. Rev. 2014, 114, 1343. (4) (a) Kitagawa, S.; Kitaura, R.; Noro, S.-i. Angew. Chem., Int. Ed. 2004, 43, 2334. (b) Lee, J.; Farha, O. K.; Roberts, J.; Scheidt, K. A.; Nguyen, S. T.; Hupp, J. T. Chem. Soc. Rev. 2009, 38, 1450. (c) Allendorf, M. D.; Bauer, C. A.; Bhakta, R. K.; Houk, R. J. T. Chem. Soc. Rev. 2009, 38, 1330. (d) Kurmoo, M. Chem. Soc. Rev. 2009, 38, 1353. (e) Li, J.-R.; Kuppler, R. J.; Zhou, H.-C. Chem. Soc. Rev. 2009, 38, 1477. (5) (a) Wu, H.; Gong, Q.; Olson, D. H.; Li, J. Chem. Rev. 2012, 112, 836. (b) Sumida, K.; Rogow, D. L.; Mason, J. A.; McDonald, T. M.; Bloch, E. D.; Herm, Z. R.; Bae, T.-H.; Long, J. R. Chem. Rev. 2012, 112, 724. (c) O’Keeffe, M.; Yaghi, O. M. Chem. Rev. 2012, 112, 675. (d) Suh, M. P.; Park, H. J.; Prasad, T. K.; Lim, D.-W. Chem. Rev. 2012, 112, 782. (e) Getman, R. B.; Bae, Y.-S.; Wilmer, C. E.; Snurr, R. Q. Chem. Rev. 2012, 112, 703. (6) (a) Horcajada, P.; Gref, R.; Baati, T.; Allan, P. K.; Maurin, G.; Couvreur, P.; Férey, G.; Morris, R. E.; Serre, C. Chem. Rev. 2012, 112, 1232. (b) Kreno, L. E.; Leong, K.; Farha, O. K.; Allendorf, M.; Van Duyne, R. P.; Hupp, J. T. Chem. Rev. 2012, 112, 1105. (c) Zhang, W.; Xiong, R.-G. Chem. Rev. 2012, 112, 1163. (d) Li, J.-R.; Sculley, J.; Zhou, H.-C. Chem. Rev. 2012, 112, 869. (e) Yoon, M.; Srirambalaji, R.; Kim, K. Chem. Rev. 2012, 112, 1196. (f) Wang, C.; Zhang, T.; Lin, W. Chem. Rev. 2012, 112, 1084. (7) (a) Lin, R.-B.; Li, F.; Liu, S.-Y.; Qi, X.-L.; Zhang, J.-P.; Chen, X.M. Angew. Chem., Int. Ed. 2013, 52, 13429. (b) Dou, Z.; Yu, J.; Cui, Y.; Yang, Y.; Wang, Z.; Yang, D.; Qian, G. J. Am. Chem. Soc. 2014, 136, 5527. (c) Lee, K.; Isley, W. C.; Dzubak, A. L.; Verma, P.; Stoneburner, S. J.; Lin, L.-C.; Howe, J. D.; Bloch, E. D.; Reed, D. A.; Hudson, M. R.; Brown, C. M.; Long, J. R.; Neaton, J. B.; Smit, B.; Cramer, C. J.; Truhlar, D. G.; Gagliardi, L. J. Am. Chem. Soc. 2014, 136, 698. (8) (a) Li, C.-J.; Lin, Z.-J.; Peng, M.-X.; Leng, J.-D.; Yang, M.-M.; Tong, M.-L. Chem. Commun. 2008, 6348. (b) Ou, Y.-C.; Wang, J.; Leng, J.-D.; Lin, Z.-J.; Tong, M.-L. Dalton Trans. 2011, 40, 3592. (c) Guo, F.-S.; Chen, Y.-C.; Liu, J.-L.; Leng, J.-D.; Meng, Z.-S.; Vrábel, P.; Orendác,̌ M.; Tong, M.-L. Chem. Commun. 2012, 48, 12219. (d) Bao, X.; Shepherd, H. J.; Salmon, L.; Molnár, G.; Tong, M.-L.; Bousseksou, A. Angew. Chem., Int. Ed. 2013, 52, 1198. (e) Bao, X.; Guo, P.-H.; Liu, W.; Tucek, J.; Zhang, W.-X.; Leng, J.-D.; Chen, X.-M.; ́ Guralskiy, I.; Salmon, L.; Bousseksou, A.; Tong, M.-L. Chem. Sci. 2012, 3, 1629. (f) Liu, W.; Bao, X.; Mao, L.-L.; Tucek, J.; Zboril, R.; Liu, J.L.; Guo, F.-S.; Ni, Z.-P.; Tong, M.-L. Chem. Commun. 2014, 50, 4059. (g) Li, J.-Y.; Yan, Z.; Ni, Z.-P.; Zhang, Z.-M.; Chen, Y.-C.; Liu, W.; Tong, M.-L. Inorg. Chem. 2014, 53, 4039. (h) Chen, Y.-C.; Qin, L.; Meng, Z.-S.; Yang, D.-F.; Wu, C.; Fu, Z.; Zheng, Y.-Z.; Liu, J.-L.; Tarasenko, R.; Orendác,̌ M.; Prokleška, J.; Sechovský, V.; Tong, M.-L. J. Mater. Chem. A 2014, 2, 9851. (9) (a) Katz, M. J.; Ramnial, T.; Yu, H.-Z.; Leznoff, D. B. J. Am. Chem. Soc. 2008, 130, 10662. (b) Lee, J. Y.; Lee, S. Y.; Sim, W.; Park, K.-M.; Kim, J.; Lee, S. S. J. Am. Chem. Soc. 2008, 130, 6902. (c) Sava, D. F.; Rohwer, L. E. S.; Rodriguez, M. A.; Nenoff, T. M. J. Am. Chem. Soc. 2012, 134, 3983. (d) Kang, Y.; Wang, F.; Zhang, J.; Bu, X. J. Am. Chem. Soc. 2012, 134, 17881. (e) Wang, C.; Volotskova, O.; Lu, K.; Ahmad, M.; Sun, C.; Xing, L.; Lin, W. J. Am. Chem. Soc. 2014, 136, 6171. (10) (a) Zheng, N.; Bu, X.; Feng, P. J. Am. Chem. Soc. 2002, 124, 9688. (b) Wang, X.-L.; Qin, C.; Wang, E.-B.; Xu, L.; Su, Z.-M.; Hu, C.W. Angew. Chem., Int. Ed. 2004, 43, 5036. (c) Rieter, W. J.; Taylor, K. M. L.; An, H.; Lin, W.; Lin, W. J. Am. Chem. Soc. 2006, 128, 9024. (d) Chandler, B. D.; Cramb, D. T.; Shimizu, G. K. H. J. Am. Chem. Soc. 2006, 128, 10403. (e) Ling, Y.; Chen, Z.-X.; Zhou, Y.-M.; Weng, L.-H.; Zhao, D.-Y. CrystEngComm 2011, 13, 1504. (f) Shustova, N. B.; McCarthy, B. D.; Dincă, M. J. Am. Chem. Soc. 2011, 133, 20126. (g) Chang, Y.-C.; Wang, S.-L. J. Am. Chem. Soc. 2012, 134, 9848. (h) Rao, X.; Song, T.; Gao, J.; Cui, Y.; Yang, Y.; Wu, C.; Chen, B.; Qian, G. J. Am. Chem. Soc. 2013, 135, 15559. (11) (a) Tong, M.-L; Chen, X.-M.; Ye, B.-H.; Ji, L.-N. Angew. Chem., Int. Ed. 1999, 38, 2237. (b) Lee, E. Y.; Jang, S. Y.; Suh, M. P. J. Am. Chem. Soc. 2005, 127, 6374. (c) Bauer, C. A.; Timofeeva, T. V.;

ASSOCIATED CONTENT

S Supporting Information *

Figures S1−S9 and crystallographic data in CIF format. This material is available free of charge via the Internet at http:// pubs.acs.org.

■

AUTHOR INFORMATION

Corresponding Authors

*(J.-H.J.) E-mail: [email protected]. *(M.-L.T.) E-mail: [email protected]. Author Contributions †

L.-L.M. and W.L. contributed equally to this work.

Notes

The authors declare no competing financial interest.

■

ACKNOWLEDGMENTS This work was supported by the “973 Project” (2014CB845602 and 2012CB821704), the National Natural Science Foundation of China (Grant Nos. 21301197 and 21121061), and Program for Changjiang Scholars and Innovative Research Team in University of China (IRT1298).

■

REFERENCES

(1) Batten, S. R.; Champness, N. R.; Chen, X.-M.; Garcia-Martinez, J.; Kitagawa, S.; Ö hrström, L.; O’Keeffe, M.; Suh, M. P.; Reedijk, J. CrystEngComm 2012, 14, 3001. (2) (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) Evans, O. R.; Lin, W. Acc. Chem. Res. 2002, 35, 511. (c) Yaghi, O. M.; Ó Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705. (d) Ockwig, N. W.; Delgado-Friedrichs, O.; O’Keeffe, M.; Yaghi, O. M. Acc. Chem. Res. 2005, 38, 176. (e) Zhang, J.-P.; Lin, Y.-Y.; Zhang, W.-X.; Chen, X.-M. J. Am. Chem. Soc. 2005, 127, 14162. (f) Robin, A. Y.; Fromm, K. M. Coord. Chem. Rev. 2006, 250, 2127. (g) Kitagawa, S.; Matsuda, R. Coord. Chem. Rev. 2007, 251, 2490. (h) Suh, M. P.; Cheon, Y. E.; Lee, E. Y. Coord. Chem. Rev. 2008, 252, 1007. (i) Lin, Z.; Tong, M.-L. Coord. Chem. Rev. 2011, 255, 421. (3) (a) Férey, G. Chem. Soc. Rev. 2008, 37, 191. (b) Dubbeldam, D.; Galvin, C. J.; Walton, K. S.; Ellis, D. E.; Snurr, R. Q. J. Am. Chem. Soc. 2008, 130, 10884. (c) Tranchemontagne, D. J.; Mendoza-Cortés, J. L.; O’Keeffe, M.; Yaghi, O. M. Chem. Soc. Rev. 2009, 38, 1257. (d) Zhao, D.; Timmons, D. J.; Yuan, D.; Zhou, H.-C. Acc. Chem. Res. 2011, 44, 123. (e) Zhang, J.-P.; Zhang, Y.-B.; Lin, J.-B.; Chen, X.-M. Chem. Rev. 2012, 112, 1001. (f) Herm, Z. R.; Wiers, B. M.; Mason, J. A.; van Baten, J. M.; Hudson, M. R.; Zajdel, P.; Brown, C. M.; Masciocchi, N.; Krishna, R.; Long, J. R. Science 2013, 340, 960. (g) Furukawa, H.; Cordova, K. E.; O’Keeffe, M.; Yaghi, O. M. Science 2013, 341, 974. 4679



Article

Settersten, T. B.; Patterson, B. D.; Liu, V. H.; Simmons, B. A.; Allendorf, M. D. J. Am. Chem. Soc. 2007, 129, 7136. (d) Guo, J.; Ma, J.F.; Liu, B.; Kan, W.-Q.; Yang, J. Cryst. Growth Des. 2011, 11, 3609. (e) Cui, Y.; Yue, Y.; Qian, G.; Chen, B. Chem. Rev. 2012, 112, 1126. (f) Shustova, N. B.; Cozzolino, A. F.; Dincă, M. J. Am. Chem. Soc. 2012, 134, 19596. (g) Liu, Y.; Pan, M.; Yang, Q.-Y.; Fu, L.; Li, K.; Wei, S.-C.; Su, C.-Y. Chem. Mater. 2012, 24, 1954. (12) Wang, Z.; Jin, C.-M.; Shao, T.; Li, Y.-Z.; Zhang, K.-L.; Zhang, H.-T.; You, X.-Z. Inorg. Chem. Commun. 2002, 5, 642. (b) Wang, P.; Ma, J.-P.; Dong, Y.-B.; Huang, R.-Q. J. Am. Chem. Soc. 2007, 129, 10620. (c) Chen, B.; Wang, L.; Zapata, F.; Qian, G.; Lobkovsky, E. B. J. Am. Chem. Soc. 2008, 130, 6718. (d) Binnemans, K. Chem. Rev. 2009, 109, 4283. (13) (a) Han, L.; Zhao, W.; Zhou, Y.; Li, X.; Pan, J. Cryst. Growth Des. 2008, 8, 3504. (b) Zhang, J.; Wu, T.; Feng, P.; Bu, X. Chem. Mater. 2008, 20, 5457. (c) Sun, L.-X.; Qi, Y.; Che, Y.-X.; Batten, S. R.; Zheng, J.-M. Cryst. Growth Des. 2009, 9, 2995. (d) Hu, S.; Zhang, Z.M.; Meng, Z.-S.; Lin, Z.-J.; Tong, M.-L. CrystEngComm 2010, 12, 4378. (14) (a) Hu, S.; Meng, Z.-S.; Tong, M.-L. Cryst. Growth Des. 2010, 10, 1742. (b) Meng, J.-X.; Li, Y.-G.; Fu, H.; Wang, X.-L.; Wang, E.-B. CrystEngComm 2011, 13, 649. (15) (a) Hu, S.; Chen, J.-C.; Tong, M.-L.; Wang, B.; Yan, Y.-X.; Batten, S. R. Angew. Chem., Int. Ed. 2005, 44, 5471. (b) Meng, J.; Wang, X.; Wang, E.; Li, Y.; Qin, C.; Xu, X. Inorg. Chim. Acta 2008, 361, 2447. (c) Hao, H.-Q.; Lin, Z.-J.; Hu, S.; Liu, W.-T.; Zheng, Y.-Z.; Tong, M.-L. CrystEngComm 2010, 12, 2225. (d) Han, Z.; Zhang, Q.; Gao, Y.; Wu, J.; Zhai, X. Dalton Trans. 2012, 41, 1332. (16) Blake, A. J.; Champness, N. R.; Chung, S. S. M.; Li, W.-S.; Schröder, M. Chem. Commun. 1997, 1675. (b) Papaefstathiou, G. S.; MacGillivray, L. R. Angew. Chem., Int. Ed. 2002, 41, 2070. (17) Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, Netherlands, 2003. (18) Trišcí̌ ková, L.; Potočňaḱ , I.; Chomič, J. Trans. Metal Chem. 2003, 28, 808. (b) Liu, X.; Guo, G.-C.; Fu, M.-L.; Liu, X.-H.; Wang, M.-S.; Huang, J.-S. Inorg. Chem. 2006, 45, 3679. (c) Etaiw, S. H.; Abd EI-Aziz, D. M.; Badr EI-din, A. S. Polyhedron 2009, 28, 873. (d) Lee, E.; Seo, J.; Lee, S. S.; Park, K.-M. Cryst. Growth Des. 2012, 12, 3834. (e) Maxim, C.; Tuna, F.; Madalan, A. M.; Avarvari, N.; Andruh, M. Cryst. Growth Des. 2012, 12, 1654. (19) Lin, Y.-Y; Lai, S.-W.; Che, C.-M.; Fu, W.-F.; Zhou, Z.-Y.; Zhu, N. Inorg. Chem. 2005, 44, 1511. (20) (a) Blatov, V. A. Cryst. Rev. 2004, 10, 249−318. (b) Blatov, V. A.; Carlucci, L.; Ciani, G.; Proserpio, D. M. CrystEngComm 2004, 6, 377. (21) (a) Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997. (b) Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond: In Structural Chemistry and Biology; Oxford University Press: New York, 1999. (c) Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210. (d) Tong, M.-L.; Chen, X.-M.; Batten, S. R. J. Am. Chem. Soc. 2003, 125, 16170. (22) Zhang, S.; Liang, H.; Liu, C. J. Phys. Chem. C 2013, 117, 2216. (23) (a) Che, C.-M.; Lai, S.-W. Coord. Chem. Rev. 2005, 249, 1296. (b) Chen, Z.-N.; Zhao, N.; Fan, Y.; Ni, J. Coord. Chem. Rev. 2009, 253, 1. (c) Yam, V. W.-W.; Wong, K. M.-C. Chem. Commun. 2011, 47, 11579. (24) (a) Jia, J.-H.; Wang, Q.-M. J. Am. Chem. Soc. 2009, 131, 16634. (b) Sun, D.; Yang, C.-F.; Xu, H.-R.; Zhao, H.-X.; Wei, Z.-H.; Zhang, N.; Yu, L.-J.; Huang, R.-B.; Zheng, L.-S. Chem. Commun. 2010, 46, 8168. (c) Jia, J.-H.; Liang, J.-X.; Lei, Z.; Cao, Z.-X.; Wang, Q.-M. Chem. Commun. 2011, 47, 4739. (d) Xiao, Y.; Wang, Q.-M. Chem.Eur. J. 2012, 18, 11184. (e) Yang, H.; Lei, J.; Wu, B.; Wang, Y.; Zhou, M.; Xia, A.; Zheng, L.; Zheng, N. Chem. Commun. 2013, 49, 300. (f) Yang, H.; Wang, Y.; Zheng, N. Nanoscale 2013, 5, 2674. (25) SHELXTL 6.10; Bruker Analytical Instrumentation: Madison, Wisconsin, USA, 2000. (26) Pennington, W. T. J. Appl. Crystallogr. 1999, 32, 1028.

4680


Controllable Self-Assembly of Two Luminescent Silver(I) Metal

Recommend Documents