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Assembly of metal-calixarene compounds with a ditetrazole linker: from isolated cluster, coordination chain to coordina-tion cage Xiaofei Zhu, Shentang Wang, Haitao Han, Xinxin Hang, Wenbing Xie, and Wuping Liao Cryst. Growth Des., Just Accepted Manuscript • DOI: 10.1021/acs.cgd.7b01127 • Publication Date (Web): 18 Oct 2017 Downloaded from http://pubs.acs.org on October 23, 2017

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Crystal Growth & Design

Assembly of metal-calixarene compounds with a ditetrazole linker: from isolated cluster, coordination chain to coordination cage Xiaofei Zhu,a, b Shentang Wang,b Haitao Han,b Xinxin Hang,b Wenbing Xie,*b Wuping Liao*b a

School of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, P. R. China.

b

State Key Laboratory of Rare Earth Resource Utilization, ERC for the Separation and Purification of REs and Thorium, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China. Supporting Information Placeholder

ABSTRACT: Three metal-calixarene compounds with N, Nbis[1(2)H-tetrazol-5-yl]amine (H3bta), [Co16Cl6(TC4A)4 (Hbta)4(CH3OH)10(OH)2(H2O)6] (CIAC-232), [Co17(TC4A)4 (bta)4(HCOO)6(CH3OH)4(H2O)4] (CIAC-233) and [Co20Cl2(TC4A)5(bta)2(atz)2(HCOO)2(ox)4(CH3OH)6(H2O)4] (CIAC-234) (H4TC4A = p-tert-butylthiacalix[4]arene, H2ox = oxalic acid, Hatz=5-aminotetrazole), were obtained under the solvothermal conditions in different solvents. CIAC-232 featured with an isolated {Co16} cluster was synthesized in the sole methanol solvent while CIAC-233 containing some coordination chains from a mixed methanol-DMF solvent. In-situ generated formic acid from the decomposition of DMF acts as the linker to bridge the isolated {Co17} clusters into the coordination chains in CIAC233. The attempt to replace the formate linkers with the oxalate anions results in the formation of a helmet-like open {Co20} coordination cage CIAC-234 due to the different coordination geometry of the oxalate anions. Magnetic properties and gas adsorption of these compounds were studied.

cages (5-(pyridin-3-yl)isophthalic acid) or 5-(5-fluoropyridin-3yl)isophthalic acid) [18] and Ni40 Johnson-type (J17) hexadecahedron ((pyridin-4-yl)isophthalate) [19] were synthesized with bifunctional ligands. So the structures and shapes of the linkers play an important role in the formation of the compounds. The well designed ligands might lead to some unprecedented structures. It is generally acknowledged that tetrazole ligands with various coordination modes can bridge metal ions/clusters into varied structures and many factors such as the solvent, pH value, counterion and temperature would influence the eventual structures. Here a ditetrazole ligand N, N-bis[1(2)H-tetrazol-5-yl]amine (H3bta) was chosen as the linker on base of the following considerations [20]: it has four reversible species of nondeprotonated H3bta, monodeprotonated H2bta-, doubly deprotonated Hbta2- and triply deprotonated bta3- anions, versatile coordination modes and flexible conformation. Three polynuclear cobalt compounds were successfully obtained with/without additional oxalic acid from different solvents under the solvothermal condition. The syntheses, crystal structures, and magnetic properties of these three compounds are presented. Moreover, N2 adsorption property of CIAC-234 was also investigated.

INTRODUCTION Coordination complexes have attracted much attention in the last decades due to their broad applications in fluorescence imaging, porous materials, magnetism and catalysis [1]. The structures and shapes of organic ligands were found to be crucial to the formation of the compounds. Calixarenes, a kind of macrocyclic ligands, were reported to be the effective multidentate ligands for the construction of polynuclear compounds [2-3]. It was found that the shuttlecock-like {MIIx-calixarene}n+ motif is a common secondary building unit (SBU) which can be linked together by some deliberately chosen di/tricarboxylates, N-donor ligands and bifunctional reagents [4-10]. For instance, some {Co24} octahedral nanocages[11] and {Co16} window frame-like squares [12] were constructed by bridging the {M4-TC4A} SBUs with aromatic di/ tri-carboxylates and their derivatives. While isolated octa/decanuclear cluster (azide anions) [13], Co24 metallamacrocycle (1,2,4triazole) [14], Ni/Co12, Co16 clusters (5-methyltetrazolates) [15] and Co32 tetragonal prismatic coordination cage (bis-tetrazole ligand) [16] were obtained with the N-donor linkers. Some Ni8/12/16, Co12/16, Co20 and Co24 coordination nanocages (inorganic phosphate or organic phosphonate ligands) [17], Co16 tetrahedral coordination

EXPERIMENTAL SECTION Materials and General Methods. H4TC4A was synthesized according by the literature method [21], and the other reagents were obtained commercially and used as received. The FT-IR spectra (KBr pellets) were recorded in the range of 400 – 4000 cm–1 on a Bruker IFS 66 V/S FT/IR spectrometer. Elemental analyses for C, H and N were performed on a Perkin-Elmer 2400. Powder X-ray diffraction (PXRD) patterns were collected on a Bruker X-ray Diffractometer with graphite monochromatized Cu-K radiation (λ = 1.5418 Å) with an increment of 0.02° in 2 θ between 5 to 50° and a scanning rate of 5 °/min. Thermogravimetric analyses (TGA) were performed on a Perkin-Elmer Thermal Analyzer under an N2 atmosphere at a heating rate of 5 °C·min-1. Fieldcooled DC magnetic susceptibility measurements were performed on polycrystalline samples using a Quantum Design MPMS XL-7 SQUID system in the temperature range 2 – 300 K and under the applied magnetic field of 1000 Oe. Diamagnetic corrections for the sample and sample holder were applied to the data. Gas adsorption measurements were carried out on an ASAP 2020 Surface Area and Porous Analyzer.

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As shown in Scheme 1, the isolated {Co16} cluster (CIAC-232) was synthesized in the sole CH3OH solvent while a 1D coordination polymer (CIAC-233) was obtained with the in-situ generated HCOO- anions in a mixed solvent of CH3OH and DMF. In order to replace the HCOO- anions in CIAC-233, oxalic acid was added into the reaction system, which leads to the formation of CIAC234 due to more coordination sites of oxalate anions. It should be noted that compounds CIAC-233 and CIAC-234 could not be obtained with formic acid or oxalic acid added into the sole MeOH system. Scheme 1 Preparation of CIAC-232-234. Syntheses of Compounds CIAC-232-234. Compound CIAC-232. A 23-ml Teflon-lined stainless steel container charged with a mixture of CoCl2·6H2O (100 mg, 0.4 mmol), H4TC4A (72 mg, 0.1 mmol), H3bta (23 mg, 0.15 mmol) and CH3OH (10 ml) was sealed and heated at 130 °C for 3 days, followed by cooling to room temperature at the rate of 4 °C·h−1. The product was isolated as yellow plate crystals in 62% yield based on Co. Elemental analysis: Calcd. (%) for C178H234Cl6Co16N36O34S16: C 41.96, H 4.60, N 9.90. Found: C, 41.46; H, 4.40, N, 9.87. IR bands (KBr pellet, cm-1): 3329(s), 1868(s), 1634(m), 1515(m), 1312(m), 1324(m), 1110(m), 955(w), 852(w), 692(w), 584(w), 472(w). Compound CIAC-233. CIAC-233 was synthesized by a similar way as CIAC-232, except that CH3OH solvent (10 ml) was substituted by a mixture of CH3OH (5 ml) and DMF (5 ml). The product was isolated as yellow block crystals in 68% yield based on Co. Elemental analysis: Calcd. (%) for C178H206Co17N36O36S16: C 43.23, H 4.17, N 10.20. Found: C 43.28, H 4.18, N, 10.18. IR bands (KBr pellet, cm-1): 3738(s), 3013(s), 1851(s), 1491(s), 1312(m), 1157(m), 955(m), 852(m), 776(m), 680(w), 575(w), 465(w). Compound CIAC-234. Compound CIAC-234 was synthesized by a similar way as CIAC-233, except that oxalic acid (9 mg, 0.05 mmol) was added into the system. The product was isolated as yellow block crystals in 65% yield based on Co. Elemental analysis: Calcd. (%) for C222H258Cl2Co20N28O50S20: C 44.33, H 4.29, N 6.52. Found: C 44.38, H 4.28, N 6.49. IR bands (KBr pellet, cm-1): 3009(s), 1509(s), 1395(s), 1333(m), 1193(m), 1098(m), 975(m), 883(m), 697(w), 584(w), 465(w). X-ray Data Collection and Structure Determination. Crystal data of CIAC-232--234 were collected on a Bruker D8 QUEST system with Cu-Kα radiation (λ = 1.54178 Å). The structures were solved by the direct method and refined by full-matrix leastsquares on F2 using the SHELXL-97 package [22]. The diffraction data were treated by the “SQUEEZE” method as implemented in PLATON. All non-hydrogen atoms except some butyl carbon atoms were refined anisotropically, and hydrogen atoms of the organic ligands were generated theoretically onto the specific atoms and refined isotropically with fixed thermal factors. The unidentified solvent molecules and counter ions were not included for both structures. Since the crystals do not diffract very well due to the structure disorder, the R factors in the final structure refinement are relatively large, but typical in such system. Selected crystal data and data collection and refinement parameters are listed in Table 1. CCDC 1553186-1553188 (CIAC-232-234) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk) RESULTS AND DISCUSSION

Scheme 2 Coordination modes of bta in CIAC-232 (a) CIAC-233 (b, c) and CIAC-234 (d). Single crystal X-ray diffraction analyses revealed that all these three compounds are feathered with some bta-bridged double shuttlecock-like Co4-TC4A SBUs (bis-Co4-TC4A SBUs) which are further interconnected into the isolated polynuclear entities or chains. The bta ligands play an important role in the formation of these compounds due to their rich coordination geometries (Scheme 2).

Figure 1. Molecular structures of bis-Co4-TC4A SBU (a) and an isolated {Co16} cluster in CIAC-232. The hydrogen atoms are omitted for clarity. Symmetry codes: i: -x+1,-y+1,-z+1.

Figure 2. Extended structure of CIAC-232. CIAC-232 crystallizes in the triclinic system with the space group Pī. The structure is featured with an isolated {Co16} cluster containing two bis-Co4-TC4A SBUs (Figure 1). There are eight crystallographically independent cobalt atoms (Co1−Co8) which are all six-coordinated. All these cobalt atoms are bonded by one sulfur bridge and two phenoxo µ2-O atoms from a calixarene molecule. Sites Co1-Co4 are also coordinated by one nitrogen atom while Co5-Co8 by two nitrogen atoms. Beside these atoms, Co1 is bonded by one water molecule and one chloride anion, Co2 and Co4 by one methanol molecule and one chloride anion, and Co3 by one methanol and one water molecule. Co5 is coordinated by one methanol, Co6 and Co7 by one water molecule, and Co8 by one chloride anion. Analyses of the bond lengths and bond valence sum calculations suggest all cobalt atoms to be divalent. Four adjacent cobalt atoms, Co1-Co4 or Co5-Co8, bond a calixarene molecule adopting the cone conformation to form a shuttlecock-like Co4-TC4A SBU which is connected with another by


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two parallel bta ligands into a bis-Co4-TC4A SBU. It is obvious that two tetrazole subunit of a bta ligand bond two different Co4TC4A SBUs by the N-N edges. Two such bis-Co4-TC4A SBUs are then interconnected into a {Co16} cluster through four Co-N bonds (Figure 1). In other words, the {Co16} cluster can be thought to be constructed by bridging four Co4-TC4A SBUs with four bta ligands. So the rich coordination sites and coordination modes are important for the formation of the {Co16} cluster. And then these clusters are stacked into an extended structure through supramolecular interactions (Figure 2).

Figure 5. Connection of bis-Co4-TC4A SBU and Co4-TC4A SBU (a), isolated helmet-like coordination cages in CIAC-234 (b, c) and that reported by ref. 17 (d). The butyl groups in (b) are omitted for clarity. The yellow polyhedron represents the cavity. Figure 3. A bis-Co4-TC4A SBU (a), a {Co17} cluster (b), coordination modes of the formate anions (c) and 1D entity of the {Co17} clusters bridged by the formate anions (d) in CIAC-233.

Figure 4. Arrangement of the coordination chains in the extended structure of CIAC-233. The butyl groups are omitted for clarity. When the sole methanol solvent was replaced by a mixed solvent of DMF and methanol, compound CIAC-233 containing some 1D coordination chains was obtained. Single-crystal X-ray diffraction reveals that the coordination chains are constructed by bridging some {Co17} subunits with the in situ generated formic acid which was produced by the decomposition of DMF. Compound CIAC-233 crystallizes in a monoclinic system with the space group C2/c. There are nine crystallographically independent Co(II) sites with three different coordination geometries (octahedral, pyramidal, and tetrahedral environment). As shown in Figure 3, two Co4-TC4A SBUs of a bis-Co4-TC4A unit bond a same tetrazole subunit of a bta ligand through two opposite N-N edges while they bond different tetrazole subunits in CIAC-232 (Figure 1). Two such bis-Co4-TC4A SBUs are bonded together through a cobalt cation located between two face-to-face bta ligands. And then the bis-Co4-TC4A SBUs are interconnected into a chain by the HCOO- anions. The chains are further stacked into a supramolecular extended structure (Figure 4). It should be noted that the formate anions act as not only the bridges but also the terminal ligands (Figure 3). Different from those parallel in CIAC-232, two pair of the bta ligands of a {Co17} cluster in CIAC-233 are not parallel to each other but with a dihedral angle of 73.7º.

Figure 6. View of the extended structure of CIAC-234. The attempt to replace the HCOO- bridges with the oxalate anions results in the formation of a helmet-like open {Co20} coordination cage (CIAC-234) which is constructed by linking two bisCo4-TC4A SBUs and one Co4-TC4A SBU with the ox ligands (Figure 5). Compound CIAC-234 also crystallizes in the monoclinic system but with the space group C2/m. There are eleven cobalt sites with different coordination geometries. As in the above compounds, four adjacent cobalt atoms bond to a calixarene molecule in the cone conformation to form a Co4-TC4A SBU. A bis-Co4-TC4A SBU forms by interconnecting two Co4TC4A SBUs with a bta ligand and an atz molecule in-situ generated by the decomposition of bta [24]. As in CIAC-233, two Co4TC4A subunits of a bis-Co4-TC4A SBU bond a same tetrazole subunit of a bta ligand through two opposite N-N edges. Two ox ligands bridge two bis-Co4-TC4A SBUs into a coordination square which is capped by a Co4-TC4A SBU to form a helmetlike open cage. This helmet-like motif is different from the reported one which is constructed by bridging five Co4-TC4A SBUs with eight HPO42− anions [17]. The extended structure is constructed by stacking the isolated open coordination cages through supramolecular interactions (Figure 6). The total potential solventaccessible volume estimated using PLATON reaches ca. 39.7%. The volumes are presumably occupied by some disordered solvent molecules (DMF and MeOH molecules) whose



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Figure 7 Plots of χM T vs T and χM-1 vs T for compound CIAC-232–234. The solid lines are the best fittings according to the Curie-Weiss equation. contribution was subtracted from the diffraction data by the Figure 8. N2 adsorption isotherms at 77 K for compound CIACSQUEEZE command. 234. Magnetic Studies. The solid state magnetic susceptibility for CONCLUSION compound CIAC-232–234 was measured in 2-300 K with an In summary, three calixarene-based coordination polynuclear applied field of 1000 Oe (Figure 7). The room temperature χMT compounds, isolated {Co16} cluster, 1D {Co17} polymer and helvalues for CIAC-232–234 are 37.4, 39.7 and 46.7 cm3 mol-1 K, met-like {Co20} cage, were obtained without/with ancillary oxalic respectively, which is in accord with the spin-orbit coupling result acid in different solvents. The in situ generated formate ligand of the Co16, Co17 and Co20 clusters.[17] When cooling from 300 to from the decomposition of DMF is crucial to the formation of 2K, the χMT values first decrease smoothly to about 100 K and coordination chains and open cages. The ditetrazole ligand -1 then drop quickly to 2 K. The χM data are fitted with the Curiebis[1(2)H-tetrazol-5-yl]amine is found to be an effective one in Weiss equations in a temperature range of 50 - 300K for CIACthe construction of metal-calixarene compounds due to its rich 232, 25 - 300K for CIAC-233 and 50-300K for CIAC-234. The coordination sites and versatile coordination modes. It seems posbest fittings gave θ = - 84.2 K for CIAC-232, θ = - 113.2 K for sible to obtain more calixarene-based coordination compounds CIAC-233 and θ = - 91.2 K for CIAC-234, which indicates an having fascinating structures and interesting properties by choosantiferromagnetic interaction between the CoII centers. The much ing some deliberated ditetrazole ligands. larger absolute value of θ for compound CIAC-233 indicates the II strongest antiferromagnetic coupling between the Co cations in ASSOCIATED CONTENT the crystal structure. Supporting Information N2 adsorption. The activated compound CIAC-234 was subjected to N2 adsorption at 77 K. For N2 adsorption measurement, Table for crystal data, powder XRD data and TGA curves. the samples of CIAC-234 were immersed in methanol for 3 days, during which the solvent was decanted and freshly replenished AUTHOR INFORMATION three times, and then dried in vacuum at 100 °C. As shown in Figure 8, the N2 adsorption isotherm exhibits a gas adsorption Corresponding Author behavior of the material having both micropores and mesopores [email protected] (W. Xie); [email protected] (W. Liao) (the pore size distribution shown in Figure S7). BrunauerNotes Emmett-Teller (BET) surface area and Langmuir Surface Area are estimated to be 237.2 and 270.4 m2·g-1, respectively. A whole The authors decare no competing financial interests. hysteresis of desorption was observed in the isotherm, which ACKNOWLEDGMENT might be due to the adsorption of the interstices between the isolated coordination cages and the partially blocked apertures in the This work was supported by National Nutural Science Foundation extended structure. of China (Nos. 21571172, 21521092 and 21471022). SKLRERU Open Research Fund (RERU2016017). The 13th Five-Year Plan for Science & Technology Research is sponsored by Department of Education of Jilin Province (No. JJKH20170542KJ) and Jilin Provincial Science Research Foundation of China (No. 20170101097JC).

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Assembly of metal-calixarene compounds with a ditetrazole linker: from isolated cluster, coordination chain to coordination cage Xiaofei Zhu,a, b Shentang Wang,b Haitao Han,b Xinxin Hang,b Wenbing Xie,*b Wuping Liao*b

Three calixarene-based coordination polynuclear compounds, isolated {Co16} cluster, 1D {Co17} polymer and helmet-like {Co20} cage, were obtained with a ditetrazole linker in different solvents.


Assembly of Metal-Calixarene Compounds with a ... - ACS Publications

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