Versatile Architectures of Silver(I) Organometallic Polymers with Tetra

Article pubs.acs.org/crystal

Versatile Architectures of Silver(I) Organometallic Polymers with Tetra-allyl Functionalized Calix[4]arene Fine-tuned by Distinct Anions Qiang Shi,†,§ Wen-zhi Luo,†,§ Bao Li,*,† Yun-peng Xie,‡ and Tianle Zhang*,† †

Key laboratory of Material Chemistry for Energy Conversion and Storage, School of Chemistry and Chemical Engineering and School of Materials Science and Engineering, Huazhong University of Science and Technology, Wuhan, Hubei 430074, P. R. China

‡

S Supporting Information *

ABSTRACT: Two silver(I)-organometallic polymers have been constructed by utilizing the different silver(I) salts and a bowlshaped calix[4]arene functionalized with tetra-allyl groups on the upper rim (L). Reacted with AgClO4 to afford 1, 1 exhibits a two-dimensional (2D) structure, where tetra-allyl-functionalized calix[4]arene units are linked through Ag−alkene interaction to generate wave-like organometallic chains and further connected by bridging by acetone molecules to afford a 2D network, giving a 2,4,4-net with the point (Schläfli) symbol {42·82·102}{42·84}2{4}2. Substituting ClO4− by NO3− as the counteranion of silver(I) salt, a three-dimensional organometallic polymer (2) encapsulating solvent molecules in the cavities was generated by connection of 2D inorganic AgNO3 layers and pillared L ligands, which gave a 3,3,4,4-net with the point (Schläfli) symbol {6·7·8}2{62·7·82· 9}2{62·72·92}{62·7}2. In addition, thermogravimetric analysis, luminescent properties, and voltammetric behavior of 1 and 2 also have been investigated. Structural results for these complexes show that the different counteranions play an important role in constructing silver(I)-organometallic polymers with thus flexible tetra-allylcalix[4]arene.

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Hardie using a tripodal cyclotriveratrylene-based ligand,13 respectively. Therefore, rational construction of porous Ag(I) organometallic polymers as host materials is still a challenge. Over the past several decades, calix[n]arene-based molecules have emerged as a class of molecular hosts due to their bowlshaped cavity and ability to interact with various guest molecules.14−20 Recently the calix[n]arenes and their derivatives have been also utilized as potential molecular units to assemble supramolecules21−32 and construct metal−organic frameworks because of the ease of modifying both on the lower and upper rims with a wide range of functional groups. These kinds of synthetic materials are usually characterized with large cavities encapsulating various small molecules,33,34 where most calixarenes are usually decorated with pyridyl and carboxylic groups.21,33−37 Considering the inherent and relatively large cavity of the bowl-shaped calix[4]arene, allyl functionalized calix[4]arene could be a reasonable ligand to construct porous organometallic polymers. In this work, it is reported that a tetra-allyl functionalized calix[4]arene with bowl-shaped cavity, 5,11,17,13-tetra-allylcalix[4]arene (L), is utilized as a ligand to

INTRODUCTION Recently coinage metal complexes of ethylene and alkenes have attracted considerable attention to elucidate the structures and understand bonding between ethylene molecules and coinage metal ions. 1−4 It is demonstrated experimentally and theoretically that in Ag(I)-ethylene complexes the content of back bonding is less than that observed in Cu(I)- and Au(I)ethylene compounds. However, Ag(I) ions possess a relatively strong ability to interact with conjugated hydrocarbons.5−9 Furthermore, in the past decade, a number of Ag(I)-alkene complexes have also been structurally characterized.10−13 Comparing the type of pyridyl and carboxyl ligands, it is interesting to observe that Ag(I) ions possibly exhibit a stronger ability to interact with independent alkene groups than conjugated hydrocarbons; thus organic molecules bearing alkene groups could also function as organic ligands to coordinate to Ag(I) ions to assemble organometallic supramolecules or construct organometallic polymers via Ag−alkene interaction.11 To date, most of the silver−alkene complexes are zero-, one- and and two-dimensional (2D) polymers without porosity, although diverse structures have been displayed, except for one three-dimensional (3D) polymer reported by Steiner using cyclotriphosphazene with six appended allyl arms as a ligand12 and another porous 3D polymer reported by © XXXX American Chemical Society

Received: October 24, 2015 Revised: November 22, 2015

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DOI: 10.1021/acs.cgd.5b01508 Cryst. Growth Des. XXXX, XXX, XXX−XXX

Crystal Growth & Design

Article

react with silver salts in order to construct porous organometallic polymers.

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RESULTS AND DISCUSSION Synthesis. The tetra-allyl functionalized calix[4]arene (L) was prepared by a reaction of calix[4]arene treated with NaH in DMF with 3-iodopropene, followed by Claisen rearrangement, according to the methods reported by Gutsche and his coworker over three decades ago.38 Then direct reactions of L with excess AgClO4 or AgNO3 in acetone or a mixture of acetone and ethanol led to two new organometallic complexes, L·2AgClO4·2(CH3)2CO·H2O (1) and L·4AgNO3·(CH3)2CO (2), respectively, which are directly deposited as crystals in relatively high yields and fully characterized, listed in Table 1.

Figure 1. (a) The perspective view of the asymmetric structure of 1 along with the atom numbering scheme (H atoms were omitted for clarity); (b) two binding modes of silver ions in 1, showing the coordinated (O5) and bridging (O6) acetone molecules (30% probability). Selected bond distances (Å): Ag1−C18C 2.460(7), Ag1−C19C 2.323(7), Ag1−C28 2.517(6), Ag1−C29 2.476(6), Ag1− O5 2.392(4), Ag1−O7 2.480(4), Ag2−C8A 2.467(7), Ag2−C9A 2.403(10), Ag2−C38 2.468(5), Ag2−C39 2.367(6), Ag2−O6 2.416(4), Ag2−O6B 2.516(4). Symmetry code: A 2 −x, 1 − y, −z; B 3 − x, 1 − y, −z; C 2 − x, 1 − y, 1 − z.

Table 1. Crystal Data of 1 and 2 chemical formula formula mass crystal system a/Å b/Å c/Å α/° β/° γ/° unit cell volume/Å3 temperature/K space group Z Rint final R1 values (I > 2σ(I)) final wR(F2) values (I > 2σ(I)) final R1 values (all data) final wR(F2) values (all data)

1

2

C46H54Ag2Cl2O15 1133.54 triclinic 11.242(7) 14.112(9) 15.132(9) 97.089(15) 94.130(15) 110.978(14) 2207(2) 293(2) P1̅ 2 0.0373 0.0512 0.1372 0.0636 0.1477

C43H46Ag4N4O17 1322.32 orthorhombic 8.9728(16) 28.041(5) 17.698(3) 90.00 90.00 90.00 4452.9(14) 293(2) Pnma 4 0.0373 0.0439 0.1106 0.0524 0.1180

Figure 2. One-dimensional wave-like organometallic chain in 1.

In their infrared spectra, the typical bands for perchlorate and nitrate anions appeared at 1108 and 1384 cm−1, respectively, along with a series of peaks belonging to organic groups, indicating that calix[4]arene ligand is coordinated to silver ions to generate organometallic complexes.39−41 Crystal Structure of 1. The X-ray single crystal diffraction study indicates that 1 crystallizes in the triclinic crystal system P1̅, and a 2D wave-like layer crystal structure is presented. In the asymmetric unit of 1 (Figure 1a), there are one calix[4]arene, two silver ions, two perchlorate anions, two coordinated acetone, and one water molecule. The calix[4]arene molecule still keeps the “cone” geometry, and each Ag ion interacts with two alkene groups in two different calix[4]arene units with Ag−C distances in the range of 2.367(6)−2.517(6) Å. Additionally both Ag ions also interact with two O atoms except for two terminal alkene groups, but the difference is that one Ag ion (Ag2) is coordinated by two O atoms in two bridging acetone molecules to form the dinuclear nodes, and another (Ag1) is bound by two O atoms from one coordinated acetone molecule and one perchlorate anion. Interestingly in 1, the bowl-shaped calix[4]arene units are connected through Ag−alkene interaction to generate a wavelike organometallic chain as shown in Figure 2. In Figure 3a, it is clearly shown that these organometallic chains are further linked by acetone molecules to generate a 2D organometallic layer. The packing drawing shows that in solid state, cavities of

Figure 3. (a) Two-dimensional organometallic network in 1 constructed by linkage of organometallic chains through bridging acetone molecules; (b) packing diagram for 1, showing water, acetone, and ClO4− anions in the cavities and channels in 1.

calix[4]arenes and the void channels are accommodated by free water and coordinated acetone molecules together with perchlorate anions (Figure 3b). Because of the connection of acetones, two silver ions could be also seen as dinuclear node, which is further stabilized by four allyl groups of different ligands. In this way, considering the mononuclear Ag ion, dinuclear Ag unit, and calix[4]arenes ligands as two-, four-, and four-connecting nodes, the 2D layer of 1 topologically possesses a 2,4,4-connected trinodal net with the point (Schläfli) symbol {42·82·102}{42·84}2{4}2 calculated with TOPOS software,43 shown in Figure 4. This net was simplified to analyze supernet-subnet relations by TOPOS as subnet of the 2,4,4-connected topology and has never been observed in silver(I)-organometallic polymers. Crystal Structure of 2. In order to investigate the effect of different anions on the Ag-tetra-allylcalix[4]arene system, the same synthetic procedure was repeated substituting ClO4− by B



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modes for nitrate anions. One nitrate anion coordinates to two Ag ions (Ag1, Ag2A), where two O atoms (O3, O4; O5, O4) interact with one Ag ion in chelating mode, but another connects two Ag ions (Ag1B, Ag2) in a bridging mode just using two O atoms (O6, O7). In one tetrameric aggregate, the Ag−O distances are in the range of 2.294(4)−2.598(3) Å. However, the Ag−O distance between the aggregates is 2.824 Å, much longer than the values found in a tetrameric aggregate, but still smaller than the sum of their van der Waals radii (3.24 Å), indicating the presence of weak interactions between the aggregates.42 In the solid state, the weak Ag···O interaction between these tetrameric AgNO3 units link them to afford an inorganic AgNO3 layer (Figure 6a). In one tetrameric AgNO3 unit, there are two Ag ions on both sides of the aggregate, which are coordinated by four alkene groups from four independent calix[4]arene molecules (Figure S2). The calix[4]arene ligands act as the pillars to connect the adjacent inorganic AgNO3 layer. In addition, two groups of calix[4]arene molecules point to different directions. In such way, tetra-allylcalix[4]arenes encapsulating solvent molecules connect inorganic AgNO3 layers as bridging ligands to generate a 3D organometallic polymer (Figure 6b and S2) (the solvent accessible volume is 10.1%). Because of the compact packing structure, the encapsulated acetones are difficult to loss or exchange at room temperature or regular methods, which could be validated by TG curve (Figure S3). In 1, one ClO4− anion acting as a monodentate ligand occupies one coordination site of tetrahedral Ag(I) ion. In contrast, the NO3− ion in 2 acting as the bridging ligand occupies two coordination sites of silver ions. The stronger coordination ability and smaller steric hindrance of NO3− must be responsible to form a higher dimensional structure compared to ClO4−. In addition, TG curves reveal that 2 are stable up to 240 °C compared to 150 °C of 1, which is also ascribed to the different architectures caused by the counteranions (Figure S3). Clearly the decomposition temperatures for 1 and 2 are lower than those observed for so-called MOFs, indicating that the interaction between Ag ion and alkene group is weak. Considering two crystallographically different silver ions, NO3− anions and calix[4]arene ligands as three-, four-, threeand four-connecting nodes, the 3D structure of 2 topologically possesses a 3,3,4,4-connected trinodal net with the point (Schläfli) symbol {6·7·8}2{62·7·82·9}2{62·72·9̂2}{62·7}2 calculated with TOPOS software,43 shown in Figure 7. This net was simplified to analyze supernet-subnet relations by TOPOS as subnet of the 3,3,4,4-connected topology and has never been observed in silver(I)-organometallic polymers. Luminescent Properties of 1 and 2. The photoluminescent properties of free ligand, complexes 1 and 2 in the solid state were investigated, shown in Figure 8. The free ligand exhibits the strongest emission peak at 344 nm (λex = 290 nm), which could be presumably attributed to the π−π* transitions. However, this strong peak could not be detected in the emission spectra of 1 and 2, indicating the fluorescence quenching of tetra-allylcalix[4]arenes after coordinating with silver ions. Voltammetric Behavior of 1 and 2. In order to further compare the effect of different anions to the properties of polymers, the voltammetric behaviors of 1 and 2 were investigated. The bulk-modified carbon paste electrodes of 1 and 2 (1-CPE and 2-CPE) were fabricated as the working electrode to study the electrochemical properties.44 The cyclic

Figure 4. Partial perspective of a simplified ball-and-stick model of the single 2D structure of 1 (the light green, dark green and purple balls represent the 2-connected Ag ions, dinuclear and 4-connected L ligands, respectively.

NO3− as the counteranion of silver(I) salt. A 3D organometallic polymer (2) encapsulating solvent molecules in the cavities was generated. The X-ray single crystal diffraction study indicates that 2 crystallizes in the orthorhombic crystal system Pnma. The asymmetric units contains two Ag ions, half calix[4]arenes ligand, two nitrate anions, and one acetone molecule (Figure 5a). As shown in Figure 5b, each Ag ion interacts with one

Figure 5. (a) The perspective view of the asymmetric structure of 1 along with the atom numbering scheme (H atoms were omitted for clarity). (b) Binding mode of L in 2 (30% probability). Selected bond distances (Å): Ag1−C17 2.403(5), Ag1−C18 2.323(6), Ag1−O3 2.389(4), Ag1−O4 2.598(3), Ag1−O6B 2.294(4), Ag2−C20 2.338(5), Ag2−C21 2.310(5), Ag2−O4C 2.399(3), Ag2−O5C 2.507(4), Ag2−O7 2.363(4). Symmetry code: A x, 0.5 − y, z; B 1.5 − x, 1 − y, −0.5 + z; C −0.5 + x, y, 0.5 − z.

alkene group in side-on fashion and two nitrate anions in different modes. In 2, silver nitrate molecules aggregate to form a series of tetrameric units with centro-symmetry, which are depicted in Figure 6a. It is observed that there are two binding

Figure 6. (a) Tetrameric aggregates of silver nitrate and binding modes of nitrate anions in 2 (30% probability). Selected bond distances (Å): N1−O3 1.246(5), N1−O4 1.256(5), N1−O5 1.238(5), N2−O6 1.245(6), N2−O7 1.259(6), N2−O8 1.215(6), Ag1C···O7 2.824. (b) 3D organometallic polymer, showing the AgNO3 layers and calix[4]arene layers encapsulating acetone molecules in 2. C



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Figure 7. Partial perspective of a simplified ball-and-stick model of the single 3D structure of 2 (the green, red, blue, and purple balls represent the 4-connected Ag ions, 3-connected Ag ions, 3-connected NO3− anions, and 4-connected L ligands, respectively.

Figure 9. Cyclic voltammograms of the 1- (top) and 2-CPEs (bottom) in 1 M sulfuric acid aqueous solution at different scanning speeds (from inside to outside: 20, 40, 60, 80, 100, 120, 160, 180, and 200 mV s−1).

Figure 8. Luminescent spectra of 1 and 2 at room temperature.

(CH3)2CO (2), the calix[4]arene molecules as bridging ligands connect inorganic AgNO3 layers directly to construct a porous 3D organometallic polymer. The obtained results demonstrate that using allyl functionalized bowl-shaped calix[4]arenes as ligands is a reasonable approach to Ag(I)-ally organometallic polymers controlled by the distinct anions. Further investigation to construct highly porous Ag(I) organometallic polymers as host materials is in progress based on this approach.

voltammograms for 1- and 2-CPE in 1 M H2SO4 aqueous solution at different scan rates are presented in Figure 9. For 2CPE, only one pair of reversible redox peaks appear with mean potentials of Epa = 229 mV and Epc = 8 mV in the potential range −500 mV to 7500 mV for 2. The half-wave potential E1/2 = (Epa + Epc)/2 (scan rate: 60 mV s−1) is 103 mV. Thus, the redox peak for 2 is attributed to an AgI/Ag0 couple. Furthermore, the peak potentials vary gradually when the scan rate was increased from 20 to 200 mV s−1. The cathodic peak potentials shift to the negative direction and the corresponding anodic peak potentials to the positive direction. Therefore, the redox process of 2-CPE should be surface controlled as confirmed by the proportional relationship between peak current and scan rate. In contrast, for 1-CPE, no obvious redox peaks could be directly observed under the same measurement conditions. The different coordination mode and environment of silver ions in 1 and 2 caused by different anions must be responsible for thus difference.

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EXPERIMENTAL SECTION

Experiments and Crystal Data. 5,11,17,13-Tetra-allylcalix[4]arene (L) is synthesized as reported in the literature.38 All the silver salts and the solvents used in this work were purchased from commercial sources and used without further purification. 1H NMR spectra were recorded on a Bruker AV-400 instrument. FT-IR spectrum was recorded on a Bruker VERTEX 70 spectrometer. Elemental analysis (C, H, N) was performed on a PerkinElmer elemental analyzer. Photoluminescence spectra were measured on a Hitachi F-7000 fluorescence spectrophotometer. Crystal structures for 1 and 2 were solved by direct methods and refined by full-matrix leastsquares using diffraction data collected on a Bruker SMART APEX CCD-based diffractometer with graphite-monochromated Mo−Kα radiation (λ = 0.71000 Å).38 In 1, one C atom (C9) is disordered over two positions with the site occupancy ratio of 0.50:0.50. In 2, one Ag ion (Ag2) is disordered over two positions with the site occupancy ratio of 0.84:0.16. TG curve was measured from 30 to 800 °C on a SDT Q600 instrument at a heating rate 10 °C/min under the N2 atmosphere (100 mL/min). Electrochemical measurements were performed with a CHI660 electrochemical workstation. A conventional three electrode system was used. The working electrode was a

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CONCLUSION In summary, 5,11,17,23-tetra-allylcalix[4]arene (L) was utilized as a ligand to prepare two new Ag(I) organometallic complexes. Crystallographic studies revealed that in L·2AgClO4·2(CH3)2CO·H2O (1), the calix[4]arene molecules are linked by Ag(I) ions to generate wave-like organometallic chains via silver−alkene interaction, which are further bridged by acetone molecules to afford a 2D polymer, and in L·4AgNO3· D



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modified carbon paste electrode. Ag/AgCl (3 M KCl) electrode was used as a reference electrode and a Pt wire as a counter electrode. L·2AgClO4·2(CH3)2CO·H2O (1). To an acetone solution of L (6.0 mg, 10.26 × 10−3 mmol, 1.5 mL) in one 5 mL vial, an ethanolic solution of AgClO4 prepared by dissolving two drops of saturated AgClO4 solution in water (about 0.56 g, 2.69 mmol) in 3 mL of ethanol was added. This capped vial was kept undisturbedly in dark at room temperature for several days. Colorless needle-like crystals for 1 were collected and dried in air (9.0 mg, yield: 78.7%). IR: 1108 (s, br). Elemental analysis calcd (%) for C46H54Cl2O15Ag2 (1133.54): C 48.74, H 4.80; found: C 49.12, H 4.61. L·4AgNO3·(CH3)2CO (2). To an acetone solution of 1 (6.0 mg, 10.26 × 10−3 mmol, 0.9 mL) in one 5 mL vial, an ethanolic solution of AgNO3 prepared by dissolving solid AgNO3 (27.6 mg, 0.164 mmol) in 3 mL hot ethanol was added. This capped vial was kept undisturbedly in dark at room temperature for several days. Pale-blue crystals for 2 were collected and dried in air (7.8 mg, yield: 57.8%). IR: 1384 (s). Elemental analysis calcd (%) for C43H46N4O17Ag4 (1322.32): C 39.06, H 3.51, N 4.24; found: C 38.79, H 3.62, N 4.11.

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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.cgd.5b01508. Figures of space-filling drawing for the solvent molecule (acetone) encapsulated in the cavity of calix[4]arene molecule in 2; binding mode of tetrameric AgNO3 aggregate in 2; TGA curves of 1 and 2 (PDF) Accession Codes

CCDC 1438207−1438208 contains 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

*(B.L.) E-mail: [email protected]. *(T.Z.) E-mail: [email protected]. Author Contributions §

Q.S. and W.L. contributed equally.

Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS We gratefully acknowledge the National Natural Science Foundation of China for financial support (Nos. 21371064 and 21471062), and the Analytical and Testing Center, Huazhong University of Science and Technology for analysis and spectral measurements.

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REFERENCES

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Versatile Architectures of Silver(I) Organometallic Polymers with Tetra

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