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34 卷 9 期 2015. 9 结 构 化 学 (JIEGOU HUAXUE) Chinese J. Struct. Chem. Vol. 34, No. 9 1371─1378 Syntheses, Structures, and Luminescent Properties of the ZnII and CdII 1-D Chain Polymers ① Assembled by Salicylhydroxamic Acid GAO Dan-Dana GAO Qianb CHEN Yan-Meib LI Ya-Hongb② LI Wua② a (Key Laboratory of Comprehensive and Highly Efficient Utilization of Salt Lake Resources, Qinghai Institute of Salt Lakes, Chinese Academy of Sciences, Xining 810008, China) b (College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China) ABSTRACT Two complexes of compositions [Zn(H2shi)(CH3COO)]n (1) and [Cd(H2shi)2(H2O)]n (2) (H3shi = salicylhydroxamic acid) have been prepared under solvothermal conditions. They are characterized by X-ray single-crystal diffraction, IR and elemental analysis. The crystal of 1 belongs to the tetragonal system, space group I41/a with a = 18.972(3), b = 18.972(3), c = 10.938(2) Å, V = 3937.1(1) Å3, C9H9NO5Zn, Mr = 276.54, Z = 16, Dc = 1.866 g/cm3, μ = 2.500 mm-1, F(000) = 2240, the final R = 0.0425 and wR = 0.123. The crystal of 2 belongs to the monoclinic system, space group P2/c with a = 16.647(3), b = 6.4577(1), c = 6.5623(1) Å, V = 702.4(2) Å3, C14H14Cd2N2O7, Mr = 434.68, Z = 2, Dc = 2.055 g/cm3, μ = 1.599 mm-1, F(000) = 432, the final R = 0.0211 and wR = 0.0761. They both possess 1-D polymeric chain structures. The luminescent properties of complexes 1 and 2 have been investigated. Keywords: hydroxamic acids, zinc complex, cadmium complex, 1-D polymeric chain, luminescent property; DOI: 10.14102/j.cnki.0254-5861.2011-0675 1 INTRODUCTION coordination behaviors of hydroxamic acid can be tuned by the incorporation of different functional Hydroxamic acids (HAs) are a valuable class of groups, e.g., -NMe2[2], -OH[6], -NH2[7], etc., at ortho, bioligands and have been extensively employed in meta and (or) para positions of the phenyl ring, [1] chemical biology . They possess high metal- generating coordination complexes with fascinating chelating affinity and exhibit versatile coordination configurations and useful properties. These properties make hydroxamic acids Salicylhydroxamic acid (H3shi) is a member of a to be powerful ligands to construct homometallic or big family of hydroxamic acids. It shows rich heterometallic polynuclear clusters and chain com- coordination modes[8-18] (Scheme 1) due to the extra plexes[2-5]. Recent advances in the coordination hydroxyl group at the meta position of phenyl ring. chemistry of hydroxamic acids reveal that the H3shi acted as a polydentate ligand to afford mo- modes. Received 9 February 2015; accepted 13 July 2015 (CCDC 996953 for 1 and 996946 for 2) ① Supported by the National Natural Science Foundation of China (21272167, 51404234 and U140710123), a project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institution and KLSLRC (KLSLRC-KF-13-HX-1) ② Corresponding authors. Li Ya-Hong, born in 1968, professor, majoring in organometallic chemistry. E-mail: [email protected]; Li Wu, born in 1966, professor, majoring in inorganic chemistry. E-mail: [email protected] GAO D. D. et al.: Syntheses, Structures, and Luminescent Properties of the ZnII and CdII 1-D Chain Polymers Assembled by Salicylhydroxamic Acid 1372 [14] No. 9 and Pt [13] , e.g. cleavage of DNA, RNA and amino acid esters, generating polynuclear compounds with Cu [10] , etc.[23-27], and in organic synthesis[28]. To further Mo[11], and V[12] as well as polynuclear heterome- explore the coordination chemistry of salicylhydro- nonuclear complexes with Ru [18] , V [10] . To our tallic Mn-Ho and Mn-Dy complexes surprise, no polynuclear coordination complexes of II II Zn and Cd are reported. As is well known, coorII II xamic acid with ZnII and CdII, we conducted the reaction of salicylhydroxamic Zn(CH3COO)2·2H2O and acid with Cd(CH3COO)2·2H2O, dination complexes of Zn and Cd have attracted a respectively. Two new 1-D polymeric chain com- great deal of interest due to their potential applica- plexes with formulas [Zn(H2shi)(CH3COO)]n (1) and [19-21] , such [Cd(H2shi)2(H2O)]n (2) were synthesized. Herein, we as light-emitting diodes (LEDs) and organic light- report the syntheses, structures and luminesient tions in fluorescence-emitting materials [22] , in biological systems, emitting diodes (OLEDs) Scheme 1. 2 properties of these two complexes. Coordination modes of H3shi EXPERIMENTAL 2. 2. 1 Synthesis of [Zn(H2shi)(CH3COO)]n (1) A mixture of Zn(CH3COO)2·2H2O (0.0216 g, 2. 1 Materials and physical measurement 0.10 mmol), H3shi (0.0153 g, 0.10 mmol), and H2O All chemicals were purchased from commercial (1.0 mL) was placed in a Pyrex-tube. The tube was suppliers and used without further purification. The heated at 80 ℃ for 6 days. After being cooled to C, H and N microanalyses were carried out with a room temperature, pale yellow crystals of the Carlo-Erba EA1110 CHNO-S elemental analyzer. product were afforded. The crystals were collected FT-IR spectra were recorded from KBr pellets in the by filtration, washed with H2O (2 mL) and dried in -1 on a Nicolet MagNa- air. Yield: 40% (based on Zn). Anal. Calcd. (%) for IR500 spectrometer. Crystal determination was C9H9NO5Zn: C, 39.09; H, 3.28; N, 5.06. Found (%): performed with a Bruker SMART APEX ΙΙ CCDC C, 38.96; H, 3.15; N, 5.01. IR (KBr, cm-1): 3274(s), diffractometer 1612(s), 1551(s), 1481(s), 1367(m), 1250(m), range of 400~4000 cm equipped with graphite-mono- chromatized MoKα radiation (λ = 0.71073 Å). The 1153(s), 1059(s), 1031(m), 925(s), 812(m), 751(m). solid-state luminescence emission/excitation spectra 2. 2. 2 Synthesis of [Cd(H2Shi)2(H2O)]n (2) A mixture of Cd(CH3COO)2·2H2O (0.0207 g, 0.10 mmol), H3shi (0.0153 g, 0.10 mmol), and H2O (1.0 mL) was placed in a Pyrex-tube. The tube was heated at 80 ℃ for 7 days. After being cooled to room temperature, pale yellow crystals of the product were afforded. The crystals were collected were recorded on a FLS920 fluorescence spectrophotometer equipped with a continuous Xe-900 xenon lamp and a μF900 microsecond flash lamp. Powder X-ray diffraction (PXRD) was recorded on a Rigaku D/Max-2500 diffractometer. 2. 2 Syntheses of the complexes 2015 Vol. 34 结 构 化 学(JIEGOU HUAXUE)Chinese by filtration, washed with H2O (2 mL) and dried in air. Yield: 56% (based on Cd). Anal. Calcd. (%) for C14H14Cd2N2O7: C, 38.68; H, 3.25; N, 6.44. Found (%): C, 38.76; H, 3.21; N, 6.38. IR (KBr, cm-1): 3468(m), 3015(w), 1613(s), 1549(s), 1481(s), 1417(s), 1341(s), 1250(s), 1153(s), 1122(s), 1050(s), 925(s), 812(m), 751(s), 659(s). 2. 3 X-ray crystal structure determination The single crystals of complexes 1 and 2 were determined with MoKα radiation using a Bruker SMART APEX-II CCD diffractometer at 296(2) K for 1 and 293(2) K for 2 using the ω-2θ scan mode. Table 1. J. Struct. Chem. 1373 For complex 1, in the range of 2.15≤θ≤28.42o, a total of 13821 reflections were obtained with 2490 unique ones and used in the refinements. For complex 2, in the range of 3.39≤θ≤27.49o, a total of 5355 reflections were obtained with 1573 unique ones and used in the refinements. The structures were solved by direct methods and refined with full-matrix least-squares on F2 using SHELXS-97[29] and SHELXL-97[30]. The selected bond lengths and bond angles of complexes 1 and 2 are listed in Table 1. Selected Bond Lengths (Å) and Bond Angles (°) 1 Bond Dist. Bond Dist. Bond Dist. Zn(1)–O(4)#1 1.983(2) Zn(1)–O(2)#1 1.997(2) Zn(1)–O(3) 2.095(3) Zn(1)–O(2) 2.035(2) Zn(1)–O(1) 2.046(2) Angle (°) Angle (°) Angle (°) O(4)#1–Zn(1)–O(2)#1 97.34(1) O(4)#1–Zn(1)–O(2) 165.92(1) O(2)#1–Zn(1)–O(2) 96.68(1) O(2)#1–Zn(1)–O(1) 109.76(1) O(2)–Zn(1)–O(1) 78.86(9) O(2)#1–Zn(1)–O(3) 97.83(1) O(1)–Zn(1)–O(3) 151.59(1) O(2)–Zn(1)–O(3) 91.63(1) O(4)#1–Zn(1)–O(1) 95.15(1) O(4)#1–Zn(1)–O(3) 87.73(1) N(1)–O(2)–Zn(1)#2 114.30(2) N(1)–O(2)–Zn(1) 109.75(2) Zn(1)#2–O(2)–Zn(1) 129.73(1) 2 Bond Dist. Bond Dist. Bond Dist. Cd(1)–O(1) 2.341(2) Cd(1)–O(3)#2 2.3533(2) Cd(1)–O(1)#3 2.4323(2) Cd(1)–O(1W) 2.366(2) Angle (°) Angle (°) Angle (°) O(1)#1–Cd(1)–O(1) 179.48(5) O(1)#1–Cd(1)–O(3)#2 91.04(6) Cd(1)–O(1)–Cd(1)#2 103.12(6) O(1)–Cd(1)–O(3)#2 89.12(6) O(1)–Cd(1)–O(3)#3 91.04(6) O(1W)–Cd(1)–O(1)#2 137.13(4) O(3)#2–Cd(1)–O(3)#3 144.33(7) O(1)#1–Cd(1)–O(1W) 90.26(2) O(3)#2–Cd(1)–O(1)#2 66.99(5) O(1)–Cd(1)–O(1W) 90.26(2) O(3)#2–Cd(1)–O(1W) 72.17(4) O(3)#3–Cd(1)–O(1)#2 147.12(5) O(1)#1–Cd(1)–O(1)#3 76.88(6) O(1)–Cd(1)–O(1)#3 102.73(6) O(1)#1–Cd(1)–O(1)#2 102.73(6) O(3)#2–Cd(1)–O(1)#3 147.12(5) O(3)#3–Cd(1)–O(1)#3 66.99(5) O(1)–Cd(1)–O(1)#2 76.88(6) O(1W)–Cd(1)–O(1)#3 137.13(4) O(1)#3–Cd(1)–O(1)#2 85.74(7) O(3)#3–Cd(1)–O(1W) 72.17(4) N(1)–O(1)–Cd(1) 110.68(1) N(1)–O(1)–Cd(1)#2 108.95(1) O(1)–Cd(1)–O(1W) 90.26(2) N(1)–O(1)–Cd(1)#2 108.95(1) O(1)#1–Cd(1)–O(3)#3 89.12(6) 3 RESULTS AND DISCUSSION 3. 1 Structure descriptions of the complexes 3. 1. 1 Structure of complex 1 The crystal structure analysis reveals that 1 crystallizes in the tetragonal crystal system, space group I41/a. The asymmetric unit (Fig. 1) consists of one crystallographically independent ZnII atom, one H2shi- ligand and one acetate ion. The ZnII ion is penta-coordinated by one carboxyl oxygen atom, one μ2-hydroxamate oxygen atom and one μ1- hydroxamate oxygen atom from two H2shi- ligands, and two oxygen atoms from acetate ions, displaying distorted tetragonal geometry. The adjacent ZnII ions are doubly connected by two oxygen atoms of the acetate ion and one hydroxamate oxygen atom to generate an infinitive 1-D chain structure (Fig. 2). The Zn–O/N bond lengths are in the range of 1.983(2)~2.095(3) Å. The ZnII···ZnII distance is 3.6506(7) Å. The H2shi- ligands possess the coordination mode F (Scheme 1). GAO D. D. et al.: Syntheses, Structures, and Luminescent Properties of the ZnII and CdII 1-D Chain Polymers Assembled by Salicylhydroxamic Acid 1374 Fig. 1. No. 9 Coordination environment of the Zn ion in 1. Hydrogen atoms have been omitted for clarity. Color scheme: blue, ZnII; red, oxygen; dark blue, nitrogen; yellow, carbon Fig. 2. 1-D chain structure of 1. Hydrogen atoms are omitted for clarity. Color scheme: blue, ZnII; red, oxygen; dark blue, nitrogen; yellow, carbon 3. 1. 2 μ2-hydroxamate oxygen atom (coordination mode F Structure of complex 2 The crystal structure analysis reveals that 2 in Scheme 1), with the Cd–O distances ranging crystallizes in monoclinic, space group P2/c. The from 2.341(2) to 2.432(16) Å. The Cd···Cd distance crystal structure of 2 (Fig. 3) consists of one Cd II - is 3.7392(6) Å. ion and two singly deprotonated H2shi ligands and Remarkably, complexes 1 and 2 were prepared by II using similar starting materials, but their com- ions are bridged by the hydroximate oxygen atoms positions and structures are totally different, indica- to form a one-dimensional linear chain (Fig. 4). ting that metal ions play key roles in the construc- one coordinated water molecule. The adjacent Cd II Each Cd ion is bound to seven oxygen atoms (O1, O1A, O3A, O3B, μ2-O1B, μ2-O1C, and O1W) - tion of coordination polymers. Complexes 1 and 2 join a big family of coor- originated from four different H2shi ligands and dination polymers of ZnII/CdII[31-36]. However, the one water molecule. Each H2shi- ligand chelates one ZnII and CdII 1-D chain complexes supported by the CdII ion through a μ1-carbonyl oxygen atom and a H3shi ligand are never reported. 2015 Vol. 34 Fig. 3. 结 构 化 学(JIEGOU HUAXUE)Chinese J. Struct. Chem. 1375 Coordination environment of the Cd ion in 2. Hydrogen atoms have been omitted for clarity. Color scheme: green, CdII; red, oxygen; blue, nitrogen; yellow, carbon Fig. 4. 1-D chain structure of 2. Hydrogen atoms are omitted for clarity. Color scheme: green, CdII; red, oxygen; blue, nitrogen; yellow, carbon 3. 2 Powder X-ray diffraction (PXRD) and complexes 1 and 2 were investigated in the In order to check the phase purity of complexes 1 solid state at room temperature (Fig. 7). The H3shi and 2, the powder X-ray diffractions (PXRD) have ligand shows photoluminescence emission at 344 been measured and compared with those simulated nm. Complex 1 shows emission with the maximum from the single-crystal structure data. As can be peak at 356 nm. Compared with the H3shi ligand, seen from Figs. 5 and 6, the experimental PXRD the red-shifted emission of 1 may be ascribed as the patterns and simulated peaks match well, indicating intraligand charge transfer (π-π*)[33, the purities of the complexes. nounced fluorescence emission of complex 1 3. 3 reveals its potential application in photoactive Luminescent property The luminescent properties of the H3shi ligand materials. 37] . The pro- GAO D. D. et al.: Syntheses, Structures, and Luminescent Properties of the ZnII and CdII 1-D Chain Polymers Assembled by Salicylhydroxamic Acid 1376 Fig. 5. Powder XRD patterns of complex 1 Fig. 6. No. 9 Powder XRD patterns of complex 2 H3Shi Normalized Intensity Complex 1 300 350 400 450 Wavelength/nm Fig. 7. Emission spectra of the H3shi ligand and complex 1 in the solid state at room temperature (Emission slit = 1 nm) No emission was observed for complex 2. The plexes of compositions [Zn(H2shi)(CH3COO)]n (1) water in lattice may prevent an efficient intraligand and [Cd(H2shi)2(H2O)]n (2) have been prepared charge transfer. under solvothermal conditions. The luminescent properties have been investigated. Complex 1 4 shows red-shifted luminescence emission. The CONCLUSION pronounced fluorescence emission of 1 reveals its II II In summary, two 1D chain Zn and Cd com- potential applications for photoactive materials. REFERENCES (1) Codd, R. 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