A Chain Cadmium(II) Coordination Polymer with Diacylhydrazide: Synthesis, Crystal Structure and Luminescent Property

Kai WANG Xu-Ke HUANG Li ZHU Zi-Lu CHEN Fu-Pei LIANG

Citation:  WANG Kai, HUANG Xu-Ke, ZHU Li, CHEN Zi-Lu, LIANG Fu-Pei. A Chain Cadmium(II) Coordination Polymer with Diacylhydrazide: Synthesis, Crystal Structure and Luminescent Property[J]. Chinese Journal of Structural Chemistry, 2016, 35(12): 1912-1919. doi: 10.14102/j.cnki.0254-5861.2011-1230 shu

A Chain Cadmium(II) Coordination Polymer with Diacylhydrazide: Synthesis, Crystal Structure and Luminescent Property

English

  • The design and synthesis of metal coordination polymers have attracted considerable attention not only due to their intriguing structures and topo-logies[1],but also to their potential applications in various fields,such as magnetism,gas adsorption andseparation,nonlinear optics,heterogeneous catalysis,luminescence and so on[2-7]. To obtain coordination polymers with desirable properties and expected structures,the judicious choice of ligands is one of the key factors. Up to now,various organic bridging ligands with versatile coordination capabili-ties,such as carboxylates,linear pyridine derivatives and other heterocyclic compounds,have been extensively employed in the preparation of coor-dination polymers[8-10]. It is interesting that some of the multidentate ligands,which were often used to isolate clusters with discrete structures,can also achieve coordination polymers with fascinating architectures and promising properties[11, 12].

    As a kind of multidentate ligands,diacylhydra-zides contain two hydrazide groups,thus they bear multiple coordination sites composed of both N-and O-donors and have the possibility to fulfill variable coordination modes. These structural features make them be in favor of the construction of polynuclear clusters. Bearing this in mind,our group is interested in the study of coordination chemistry for the ligands of this type in recent years[13, 14]. In our pre-vious work,wehave designed and synthesized a diacylhydrazide ligand of N,N΄-bis(salicyl)-2,6-pyridinedicarbohydrazide (H6sphz),which has assembled a novel {Cu6(sphz)2(py)4} cluster-based coordination polymer with Cu salt through solvo-thermal reaction[13]. It deserved to be mentioned that thispolymer has the highest-nuclear cluster-based Second Building Units (SBUs) among the N-acyl-salicylhydrazide-containing coordination polymers constructed without any other auxiliary ligand,implying the abilities of diacylhydrazide ligands in the construction of novel coordination polymers. As a continuation of this work,we substituted the salicyl terminal groups of H6sphz with 3-methoxy-salicyl ones to synthesize another diacylhydrazide ligand H6msphz,in the hope of investigating the influence of terminal groups for the structures and properties of the resultant complexes (Scheme 1) . Thesolvothermal reaction of Cd(CH3COO)2·2H2O and H6msphz yieldeda novel Cd(II) coordination polymer (1) . Herein,we report the synthesis and structure of complex 1. Meanwhile,the solid state luminescent property of 1 was also investigated.

    All reagents were used as received without further purification. IR spectra were recordedin the range of 4000~400 cm-1 on a Perkin-Elmer SpectrumOne

    FT/IR spectrometer using a KBr pellet. Elemental analyses for C,H and N were carried out ona Model 2400 II,Perkin-Elmer elemental analyzer. The pow-der X-ray diffraction (PXRD)data were collected with a Rigaku D/max 2500v/pc diffractometer with Cu-radiation (λ = 1.5418 Å). The thermal analy-sis was performed on a Pyris Diamond TG/DTA at a heating rate of 10 ℃ min-1 in a N2 atmosphere. Fluorescence spectroscopy of the complex and ligand were performed on an Edinburgh Analytical instrument FLS920.

    The synthetic route for ligand H6msphz is pre-sented in Scheme 1. Starting from 3-methoxyl methyl salicylate,the intermediate 3-methoxyl Sali-cyhydrazide was synthesized accordingto the literature[13, 15]. Subsequently,a THF solution (20 mL)of 2,6-pyridinedicarboxylic acid chloride (10mmol),which was prepared from the reaction of 2,6-pyridinedicarboxylic acid (1.68 g,10 mmol) with thionyl chloride (20 mL),was added slowly into a THF (30 mL) solution of Et3N (2.3 mL) and 3-metho xyl salicylhydrazide (3.04 g,20 mmol) at 0℃. The reaction mixturewas slowly warmed to ambienttemperature and was further stirredfor 2 days. Finally,a white precipitate was obtained after concentration and filtration. The recrystallization of the crude product in MeOH-H2O gave whiteprecipitate of H6msphz with a yield of 85%. 1HNMR (DMSO-d6,500 MHz) δ: 11.80 (s,2H),11.34 (s,2H),10.82 (s,2H),8.28~8.32 (m,3H),7.50~7.51 (dd,2H,J = 1.1) ,7.16~7.18 (dd,2H,J = 1.0) , 6.88~6.92 (t,2H,J = 8.2) ,3.80 (s,2H),2.47~2.48 (m,2H); 13C NMR (DMSO-d6,125 MHz) δ: 167.78, 162.12,159.08,147.69,140.11,134.27,128.47, 125.36,119.21,117.42,114.80. ESI-MS: [M-H]-: 494.06. IR (KBr pellet,cm-1) : 3505(m),3268(m), 2841,1695(m),1637(m),1585(s),1500(m),1361(s),1289(s),1252(m),1071(m),741(m). Elemental analysis Calcd. (%): C,55.90; H,4.32; N,14.19%. Found: C,55.81; H,4.28; N,14.15%.

    Figure Scheme1

    Figure Scheme1.  Synthetic route of the H6msphz ligand

    A mixture of Cd(CH3COO)2·2H2O (0.020 g, 0.075 mmol) and H6msphz (0.0123 g,0.025 mmol) in 1.5 mL DMF-Py (V/V = 1/1) was sealed in a Pyrex tube and heated to 60 ℃ for 72 h,and then cooled to room temperature at a rate of 0.5 ℃/min. Yellow block crystals of 1 were obtained with a yield of 66%. IR (KBr pellet,cm-1) : 3363(m),2834(m),1660(s),1630(s),1600(s),1444(s),1366(s), 1282(m),1224(m),1070(m),740(m). Elemental analysis Calcd. (%): C,50.37; H,3.25; N,12.37. Found (%): C,50.13; H,3.42; N,12.23.

    A single crystal of 1 with appropriate dimensions of 0.26mm × 0.20mm × 0.18mm was selected for data collection with a BrukerSMART CCD instrument by using graphite-monochromatic MoKα radiation (λ = 0.71073 Å) at 296(2) K. Absorption effects were corrected by semi-empirical methods. Thereare in total 12826 reflections collected in the range of 2.98≤θ≤25.01° (-12≤h≤12,-13≤k≤ 13,-20≤l≤20) ,of which 7116 were independent and used in the refinement (Rint = 0.0662) . The structure was solved by direct methods with SHELXS-97 program and refined by full-matrix least-squares methods with the SHELXL-97 crys-tallographic software package and Olex2[16-18]. The non-hydrogen atoms were refined ansiotropically. Thehydrogen atoms were placed in the calculated positions and refined by using a riding model. The final cycle of full-matrix least-squares refinement was based on the observed reflections and variable parameters. The final R = 0.0533 and wR = 0.1437 for 7116 observedreflections with I > 2σ (I) and R = 0.0829 and wR = 0.1765 for all data,(Δρ)max = 1.4 and (Δρ)min = -1.62 e/Å3. Selected bond lengths and bond angles are given in Table 1.

    Table 1

    Table 1.  Selected BondLengths (Å)and Bond Angles(°) of Complex 1
    DownLoad: CSV
    Bond Dist. Bond Dist. Bond Dist.
    Cd(1) -N(6) 2.377(4) Cd(1) -N(7) 2.376(6) Cd(1) -N(2) 2.306(5)
    Cd(1) -N(3) 2.441(5) Cd(1) -N(4) 2.299(6) Cd(1) -O(3) 2.503(4)
    Cd(2) -O(2) 2.158(4) Cd(1) -O(6) 2.474(4) Cd(2) -O(7)a 2.160(5)
    Cd(2) -N(9) 2.290(5) Cd(2) -O(8)a 2.594(5) Cd(2) -O(1) 2.537(4)
    Cd(2) -N(8) 2.338(7)
    Angle (°) Angle (°) Angle (°)
    N(6) -Cd(1) -N(3) 97.20(16) N(3) -Cd(1) -O(3) 132.97(15) N(9) -Cd(2) -N(8) 105.8(4)
    N(6) -Cd(1) -O(3) 85.29(15) N(3) -Cd(1) -O(6) 133.37(16) O(1) -Cd(2) -O(8) a 75.64(15)
    N(6) -Cd(1) -O(6) 86.46(15) N(4) -Cd(1) -N(6) 96.74(18) O(2) -Cd(2) -N(9) 98.96(18)
    N(7) -Cd(1) -N(6) 166.5(2) N(4) -Cd(1) -N(7) 92.3(2) O(2) -Cd(2) -O(1) 67.15(15)
    N(7) -Cd(1) -N(3) 95.6(2) N(4) -Cd(1) -N(2) 131.3(2) O(2) -Cd(2) -O(7)a 156.35(18)
    N(7) -Cd(1) -O(3) 82.9(2) N(4) -Cd(1) -N(3) 65.74(18) O(2) -Cd(2) -O(8)a 93.01(15)
    N(7) -Cd(1) -O(6) 87.78(18) N(4) -Cd(1) -O(3) 160.94(17) O(2) -Cd(2) -N(8) 93.8(3)
    N(2) -Cd(1) -N(6) 89.83(17) N(4) -Cd(1) -O(6) 67.67(18) O(7)a-Cd(2) -N(9) 96.35(19)
    N(2) -Cd(1) -N(7) 91.7(2) O(6) -Cd(1) -O(3) 93.64(14) O(7)a-Cd(2) -O(1) 95.93(17)
    N(2) -Cd(1) -N(3) 65.59(17) N(9) -Cd(2) -O(1) 86.93(19) O(7) a-Cd(2) -O(8)a 65.94(16)
    N(2) -Cd(1) -O(3) 67.47(16) N(9) -Cd(2) -O(8)a 153.12(19) O(7)a-Cd(2) -N(8) 99.2(3)
    N(2) -Cd(1) -O(6) 161.00 (17)
    Symmetry transformation: a: x-1,y+1,z

    The single-crystal X-ray diffraction study reveals that complex 1 crystallizes in triclinic space group P1 . As shown in Fig. 1,the asymmetric unit of com-plex 1 consists of two crystallographically indepen-dent Cd(II) ions,a H2msphz4- ligand and four coordinated Py molecules. The two Cd(II) ions are located in different coordination environments. The Cd(1) ion is seven-coordinated and displays a distorted pentagonal bipyramidal CdN5O2 geometry. The equatorial plane positions are occupied by a Py N(3) atom,two acylhydrazide N atoms (N(2) and N(4) ) and two acylhydrazide O atoms (O(3) and O(6) ) from H2msphz4- ligand,and the axial positions are occupied by N(3) and N(6) atoms from Py,respectively. While the Cd(2) ion is in a distorted octahedral CdN2O4 geometry,which is completed by N(8) and N(9) atoms of Py,two phenol O atoms of O(7) and O(7A) and two methoxyl O atoms of O(8) and O(8A). The Cd-O andCd-N bond distances fall in the ranges of 2.158(4) ~2.594(5) and 2.290(5) ~2.441(5) Å,respectively.

    Figure 1

    Figure 1.  Asymmetric unit and the coordination geometries of Cd(II) ions in complex 1 (Symmetry code for a: x-1,y+1,z)

    The H2msphz4- ligand adopts a rare 3-η9 coor-dination mode (Fig. 2) ,with which the ligand is not deprotonated completely and the O and N donors of diacylhydrazide groups only catch one Cd(II) ion together with two Py N donors. Meanwhile,the phenol O(7) atom and the methoxyl O(8) atom in the terminal groupschelate to the Cd(2) ion belonging to adjacent asymmetricunits,linking these units to form a chain structure (Fig. 3) . Obviously, the H2msphz4- also plays a role of linker in the chain of 1. Its coordination mode is different to that of sphz6-in [Cu6(psz)2(py)4]n,in which the sphz6-uses all of its eleven coordinating atoms to coordinate to four Cu(II) ions in a μ42:η33:η3 mode and the {Cu6} unit is further linked by the weak Cu-O bond between phenol O atomand Cu(II) ions[13]. However,both results show the potential of diacylhy drazide ligands of this type to achieve coordination polymers with novel structures.

    Figure 2

    Figure 2.  Coordination mode of H2msphz4- ligand in complex 1

    Figure 3

    Figure 3.  View of the chain structure of complex 1

    Besides,π-π interactions with centroid-to-centroid distances of 3.571(3) are found between the Py rings belonging respectively to the neighboring chains,generating supramolecular layers in the ab plane (Fig. 4) . In the c-axis direction,another kind of π-π interactions with centroid-to-centroid distances of 3.693(3) also exist between the Py rings of two adjacent layers,which led to the formation of a double-layered supramolecular structure of 1 (Fig. 5) .

    Figure 4

    Figure 4.  View of π-πinteractions betweenthe adjacent chains in the abplane of complex 1

    Figure 5

    Figure 5.  View of π-πinteractions betweenthe adjacent layers in the c-axis direction of complex1

    Compared to the solid FT-IR spectrum of H6msphz ligand,that of 1 displays peaks of 1660 and 1224 cm-1,indicating the presence of coordinated carbonyls and phenol O atoms,respectively. While a peak of 3363 cm-1 can be attributed to the stretching vibrations of -NH-groups,which were not involved in coordination. The thermogravimetric analysis (TG) wascarried out to examine the thermal stability of complex 1. The crushed single-crystal sample was heated up to 1200 ℃ in N2 at a heating rate of 10 ℃∙min-1. As shown in Fig. 6,complex 1 undergoes the first weight loss of 30.9% in the temperature range of 30~256 ℃,corresponding to the loss of coordinated Py molecules (calcd. 31.0%). The second weight loss of 44.5% occurring in the temperature range of 256 ~ 544 ℃ might be attributed to the pyrolysis of the ligand (calcd. 44.1%). Then the weight loss appears continuously asthe temperature increases. On the other hand,the PXRD experimental and computer-simulated pat-terns of the corresponding complexes are shown in Fig. 7. The PXRD pattern of the bulk sample mat-chesits simulated pattern from the single-crystal structure,demonstrating the phase purity of complex 1.

    Figure 6

    Figure 6.  TGA curve for complex 1

    Figure 7

    Figure 7.  PXRD pattern of complex 1

    Figure 8

    Figure 8.  Excitation and emission spectrafor the ligandand complex 1

    The luminescentproperties of the H6msphz ligand and complex 1 were investigated in the solid state at roomtemperature. As depicted in Fig. 8,the H6msphz ligand andcomplex 1 show strong photolu-minescence at room temperaturewith maximum emission peaks at 459 and 511 nmupon excitation at 347 and 397 nm,respectively. As is known,Cd(II) ions possess a d10 closed shell electronic configura-tion. Thus the emission of complex 1 is neither metal-to-ligand charge transfer (MLCT) nor ligand-to-metal charge transfer (LMCT),but might originate from the intraligand ππ* transitions,which are also called for ligand-to-ligand charge transfer (LLCT) and were observed frequently in other Cd coordination polymers[19-21]. On the other hand,it can be found that maximum emission peak of complex 1 display red-shift (from 459 to 511 nm) compared to that of the H6msphz ligand. This might be attributed to the coordination between the ligand and Cd(II) center,which influences the rigidity of the ligand as well as reduces the loss of energy by radiationless decay of the intraligand emission excited state[22, 23].

    In summary,we have successfully synthesized a new Cd(II) coordination polymer throughthe solvothermal reaction of Cd(CH3COO)2·2H2O with H6msphz ligand. In this complex,the H2msphz4-ligand adopts a rare 3-η9 coordination mode,by which the ligands connect the Cd(II) ions to form a chain structure. Two kinds of π-π interactions exist between the Py rings belonging to adjacent chains,leading to the formation of the final double layered supramolecular structure of 1. The luminescent property indicated that the maximum emission peak of complex 1 is 511 nm in the solid state at room temperature. This work enriches the construction of coordination polymers with multidentate diacylhy-drazide ligands.

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  • Scheme1  Synthetic route of the H6msphz ligand

    Figure 1  Asymmetric unit and the coordination geometries of Cd(II) ions in complex 1 (Symmetry code for a: x-1,y+1,z)

    Figure 2  Coordination mode of H2msphz4- ligand in complex 1

    Figure 3  View of the chain structure of complex 1

    Figure 4  View of π-πinteractions betweenthe adjacent chains in the abplane of complex 1

    Figure 5  View of π-πinteractions betweenthe adjacent layers in the c-axis direction of complex1

    Figure 6  TGA curve for complex 1

    Figure 7  PXRD pattern of complex 1

    Figure 8  Excitation and emission spectrafor the ligandand complex 1

    Table 1.  Selected BondLengths (Å)and Bond Angles(°) of Complex 1

    Bond Dist. Bond Dist. Bond Dist.
    Cd(1) -N(6) 2.377(4) Cd(1) -N(7) 2.376(6) Cd(1) -N(2) 2.306(5)
    Cd(1) -N(3) 2.441(5) Cd(1) -N(4) 2.299(6) Cd(1) -O(3) 2.503(4)
    Cd(2) -O(2) 2.158(4) Cd(1) -O(6) 2.474(4) Cd(2) -O(7)a 2.160(5)
    Cd(2) -N(9) 2.290(5) Cd(2) -O(8)a 2.594(5) Cd(2) -O(1) 2.537(4)
    Cd(2) -N(8) 2.338(7)
    Angle (°) Angle (°) Angle (°)
    N(6) -Cd(1) -N(3) 97.20(16) N(3) -Cd(1) -O(3) 132.97(15) N(9) -Cd(2) -N(8) 105.8(4)
    N(6) -Cd(1) -O(3) 85.29(15) N(3) -Cd(1) -O(6) 133.37(16) O(1) -Cd(2) -O(8) a 75.64(15)
    N(6) -Cd(1) -O(6) 86.46(15) N(4) -Cd(1) -N(6) 96.74(18) O(2) -Cd(2) -N(9) 98.96(18)
    N(7) -Cd(1) -N(6) 166.5(2) N(4) -Cd(1) -N(7) 92.3(2) O(2) -Cd(2) -O(1) 67.15(15)
    N(7) -Cd(1) -N(3) 95.6(2) N(4) -Cd(1) -N(2) 131.3(2) O(2) -Cd(2) -O(7)a 156.35(18)
    N(7) -Cd(1) -O(3) 82.9(2) N(4) -Cd(1) -N(3) 65.74(18) O(2) -Cd(2) -O(8)a 93.01(15)
    N(7) -Cd(1) -O(6) 87.78(18) N(4) -Cd(1) -O(3) 160.94(17) O(2) -Cd(2) -N(8) 93.8(3)
    N(2) -Cd(1) -N(6) 89.83(17) N(4) -Cd(1) -O(6) 67.67(18) O(7)a-Cd(2) -N(9) 96.35(19)
    N(2) -Cd(1) -N(7) 91.7(2) O(6) -Cd(1) -O(3) 93.64(14) O(7)a-Cd(2) -O(1) 95.93(17)
    N(2) -Cd(1) -N(3) 65.59(17) N(9) -Cd(2) -O(1) 86.93(19) O(7) a-Cd(2) -O(8)a 65.94(16)
    N(2) -Cd(1) -O(3) 67.47(16) N(9) -Cd(2) -O(8)a 153.12(19) O(7)a-Cd(2) -N(8) 99.2(3)
    N(2) -Cd(1) -O(6) 161.00 (17)
    Symmetry transformation: a: x-1,y+1,z
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  • 收稿日期:  2016-04-05
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