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Structural and thermal characterization of copper(II) complexes with phenyl-2-pyridylketoxime and deposition of thin films by spin coating

  • Robert Szczęsny EMAIL logo , Tadeusz M. Muzioƚ , Duncan H. Gregory and Edward Szƚyk
Published/Copyright: March 3, 2015
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Abstract

Four copper(II) oxime complexes, [Cu(HPPK)(PPK)X] (HPPK = phenyl-2-pyridylketoxime and X = CI (I ), CF3COO− (II ), C3F7COO− (III ), and [Cu(PPK)2]2 (IV )), were synthesized and characterized by elemental analysis, infrared spectroscopy (IR), and single-crystal X-ray diffraction (XRD). XRD analysis revealed that I -III contain copper(II) coordinated by four nitrogen atoms from two oxime molecules in the basal plane and one monodentate anion X in the apical position of a distorted square pyramid. Complex IV is dimeric and it is formed by two Cu(PPK)2 units. Bridges between these units are formed by the two oxygen atoms of the deprotonated oxime groups. Thermal stability of I -IV was investigated by thermogravimetric analysis (TGA) in air and in nitrogen atmosphere, respectively. Evolved gaseous decomposition products were characterized by IR. I -IV decompose via multistep processes. Fluorocarbons and CO2 were observed to be the most abundant gaseous species evolved. Preliminary ammonolysis experiments were performed to examine the possibility of using II and IV as precursors for the synthesis of copper nitride. Moreover, solutions of IV were spin-coated onto silicon substrates. Surface structure and morphology of the resulting films were studied by scanning electron microscopy (SEM) and atomic force microscopy (AFM) and layers with island-like distribution of material were observed

References

Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J., & Verschoor, G. C. (1984). Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen-sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2_-yl)-2,6- dithiaheptane]copper(II) perchlorate. Journal of the Chemical Society, Dalton Transactions, 1984, 1349-1356. DOI: 10.1039/dt9840001349.Search in Google Scholar

Afrati, T., Dendrinou-Samara, C., Raptopoulou, C., Terzis, A., Tangoulis, V., & Kessissoglou, D. P. (2007). Copper inverse-9-metallacrown-3 compounds showing antisymmetric magnetic behaviour. Dalton Transactions, 2007, 5156-5164. DOI: 10.1039/b708767e.Search in Google Scholar

Afrati, T., Pantazaki, A. A., Dendrinou-Samara, C., Raptopoulou, C., Terzis, A., & Kessissoglou, D. P. (2010). Copper inverse-9-metallacrown-3 compounds interacting with DNA. Dalton Transactions, 39, 765-775. DOI: 10.1039/ b914112j.Search in Google Scholar

Ando, M., Kobayashi, T., Iijima, S., & Haruta, M. (2003). Optical CO sensitivity of Au-CuO composite film by use of the plasmon absorption change. Sensors and Actuators B: Chemical, 96, 589-595. DOI: 10.1016/s0925-4005(03)00645-2.Search in Google Scholar

Baker, P. G. L., Sanderson, R. D., & Crouch, A. M. (2007). Sol-gel preparation and characterisation of mixed metal tin oxide thin films. Thin Solid Films, 515, 6691-6697. DOI: 10.1016/j.tsf.2007.01.042.Search in Google Scholar

Barreca, D., Gasparotto, A., Maccato, C., Tondello, E., Lebedev, O. I., & Van Tendeloo, G. (2009). CVD of copper oxides from a β-diketonate diamine precursor: tailoring the nanoorganization. Crystal Growth & Design, 9, 2470-2480. DOI: 10.1021/cg801378x.Search in Google Scholar

Bayansal, F., C¸ etinkara, H. A., Kahraman, S., C¸akmak, H. M., & G¨uder, H. S. (2012). Nano-structured CuO films prepared by simple solution methods: Plate-like, needle-like and network-like architectures. Ceramics International, 38, 1859-1866. DOI: 10.1016/j.ceramint.2011.10.011.Search in Google Scholar

Brandenburg, K. (2001). Diamond, Release 2.1e [computer software]. Bonn, Germany: Crystal Impact.Search in Google Scholar

Bräuer, B., Zahn, D. R. T., R¨uffer, T., & Salvan, G. (2006). Deposition of thin films of a transition metal complex by spin coating. Chemical Physics Letters, 432, 226-229. DOI: 10.1016/j.cplett.2006.10.070.Search in Google Scholar

Bucci, R., Carunchio, V., Magri, A. D., & Magri, A. L. (1984). The thermal decomposition reactions of bis-(pyridine-2- aldoxime)-copper(II) complexes. Journal of Thermal Analysis and Calorimetry, 29, 679-686. DOI: 10.1007/bf01913525.Search in Google Scholar

Chakravorty, A. (1974). Structural chemistry of transition metal complexes of oximes. Coordination Chemistry Reviews, 13, 1-46. DOI: 10.1016/s0010-8545(00)80250-7. Oxford Diffraction (2000). CrysAlis RED and CrysAlis CCD [computer software]. Abingdon, UK: Oxford Diffraction.Search in Google Scholar

Elschner A., Heuer, H. W., Jonas, F., Kirchmeyer, S., Wehrmann, R., & Wussow, K. (2001). Gallium complexes in threelayer organic electroluminescent devices. Advanced Materials, 13, 1811-1814. DOI: 10.1002/1521-4095(200112)13:23 <1811::AID-ADMA1811>3.0.CO;2-G.Search in Google Scholar

Farrugia, L. J. (1997). ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI). Journal of Applied Crystallography, 30, 565. DOI: 10.1107/s0021889 897003117.Search in Google Scholar

Hall, D. B., Underhill, P., & Torkelson, J. M. (1998). Spin coating of thin and ultrathin polymer films. Polymer Engineering & Science, 38, 2039-2045. DOI: 10.1002/pen.10373.Search in Google Scholar

Hudák, A., & Košturiak, A. (1999). Preparation, IR characterization and thermal properties of some metal complexes of isatin-3-oxime. Journal of Thermal Analysis and Calorimetry, 58, 579-587. DOI: 10.1023/a:1010148310379.Search in Google Scholar

Huh, P. H., Yang, J. Y., & Kim, S. C. (2012). Facile formation of nanostructured 1D and 2D arrays of CuO islands. RSC Advances, 2, 5491-5494. DOI: 10.1039/c2ra20097j.Search in Google Scholar

Ji, Z. G., Yuan, Y. H., Yuan, Y., & Wang, C. (2006). Reactive DC magnetron deposition of copper nitride films for write-once optical recording. Materials Letters, 60, 3758-3760. DOI: 10.1016/j.matlet.2006.03.107.Search in Google Scholar

Juza, R., & Hahn, H. (1939). Kupfernitrid Metallamide und Metallnitride. VII. Zeitschrift f¨ur Anorganische und Allgemeine Chemie, 241, 172-178. DOI: 10.1002/zaac.19392410 204. (in German) Search in Google Scholar

Juza, R., & Rabenau, A. (1956). Das elektrische Leitvermogen einiger Metallnitride. Zeitschrift fur Anorganische und Allgemeine Chemie, 285, 212-220. DOI: 10.1002/zaac.19562850 314. (in German) Kida, T., Oka, T., Nagano, M., Ishiwata, Y., & Zheng, X. G. (2007). Synthesis and application of stable copper oxide nanoparticle suspensions for nanoparticulate film fabrication. Journal of the American Ceramic Society, 90, 107-110. DOI: 10.1111/j.1551-2916.2006.01402.x.Search in Google Scholar

Kim, S. G., Hagura, N., Iskandar, F., Yabuki, A., & Okuyama, K. (2008). Multilayer film deposition of Ag and SiO2 nanoparticles using a spin coating process. Thin Solid Films, 516, 8721-8725. DOI: 10.1016/j.tsf.2008.05.053.Search in Google Scholar

Koumousi, E. S., Raptopoulou, C. P., Perlepes, S. P., Escuer, A., & Stamatatos, T. C. (2010). Strong antiferromagnetic coupling in doubly N,O oximato-bridged dinu clear copper(II) complexes. Polyhedron, 29, 204-211. DOI: 10.1016/j.poly.2009.07.010. Search in Google Scholar

Li, Q., Mei, P., & Xiang, J. (2006). Di--chloro-bis[chloro (phenyl 2-pyridyl ketone oxime-κ2N, N)copper(II)]. Acta Crystallographica Section E, 62, m2348-m2349. DOI: 10. 1107/s1600536806033836. Search in Google Scholar

Liu, C. H., & Liu, C. F. (1961). Hetero-binuclear chelates of copper(II) and silver(I). Journal of the American Chemical Society, 83, 4167-4169. DOI: 10.1021/ja01481a015.Search in Google Scholar

Liu, G. X., Yang, H., Nishihara, S., & Ren, X. M. (2010). A trinuclear Cu(II) complex from the use of phenyl 2-pyridyl ketoxime: Structure and magnetic behavior. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 40, 421-424. DOI: 10.1080/15533174.2010.492557.Search in Google Scholar

Meek, T. L., & Cheney, G. E. (1965). The copper(II) synphenyl-2-pyridyl ketoxime system. Part I. Canadian Journal of Chemistry, 43, 64-74. DOI: 10.1139/v65-009.Search in Google Scholar

Milios, C. J., Kefalloniti, E., Raptopoulou, C. P., Terzis, A., Escuer, A., Vicente, R., & Perlepes, S. P. (2004). 2-Pyridinealdoxime [(py)CHNOH] in manganese(II) carboxylate chemistry: mononuclear, dinuclear, tetranuclear and polymeric complexes, and partial transformation of (py)CHNOH to picolinate(-1). Polyhedron, 23, 83-95. DOI: 10.1016/j.poly.2003.09.009.Search in Google Scholar

Milios, C. J., Stamatatos, T. C., & Perlepes, S. P. (2006). The coordination chemistry of pyridyl oximes. Polyhedron, 25, 134-194. DOI: 10.1016/j.poly.2005.07.022.Search in Google Scholar

Mohan, M., & Paramhans, B. D. (1980). Transition metal chemistry of oxime-containing ligands, part XI. Copper(II) complexes of syn-phenyl-2-pyridylketoxime and syn-methyl-2-pyridylketoxime. Transition Metal Chemistry, 5, 113-117. DOI: 10.1007/bf01396885.Search in Google Scholar

Nasui, M., Mos, R. B., Petrisor, T., Jr., Gabor, M. S., Varga, R. A., Ciontea, L., & Petrisor, T. (2011). Synthesis, crystal structure and thermal decomposition of a new copper propionate [Cu(CH3CH2COO)2] · 2H2O. Journal of Analytical and Applied Pyrolysis, 92, 439-444. DOI: 10.1016/j.jaap.2011.08.005.Search in Google Scholar

Navío, C., Alvarez, J., Capitan, M. J., Camarero, J., & Miranda, R. (2009). Thermal stability of Cu and Fe nitrides and their applications for writing locally spin valves. Applied Physics Letters, 94, 263112. DOI: 10.1063/1.3159630.Search in Google Scholar

Paniconi, G., Stoeva, Z., Doberstein, H., Smith, R. I., Gallagher, B. L., & Gregory, D. H. (2007). Structural chemistry of Cu3N powders obtained by ammonolysis reactions. Solid State Sciences, 9, 907-913. DOI: 10.1016/j.solidstatesciences.2007.03. 017.Search in Google Scholar

Partridge, A., Toussaint, S. L. G., & Flipse, C. F. J. (1996). An AFM investigation of the deposition of nanometer-sized rhodium and copper clusters by spin coating. Applied Surface Science, 103, 127-140. DOI: 10.1016/0169-4332(96)00520-x.Search in Google Scholar

Prasad, R. (2003). Mechanism and kinetics of thermal decomposition of ammoniacal complex of copper oxalate. Thermochimica Acta, 406, 99-104. DOI: 10.1016/s0040-6031(03)00225-9.Search in Google Scholar

Prathapachandra Kurup, M. R., Chandra, S. V., & Muraleedharan, K. (2000). Synthesis, spectral and thermal studies of o-vanillin oxime complexes of zinc(II), cadmium(II) and mercury( II). Journal of Thermal Analysis and Calorimetry, 61, 909-914. DOI: 10.1023/a:1010154810885.Search in Google Scholar

Salonen, M., Saarinen, H., & Orama, M. (2003). Formation of zinc(II) and cadmium(II) complexes with pyridine oxime ligands in aqueous solution. Journal of Coordination Chemistry, 56, 1041-1047. DOI: 10.1080/00958970310001596737.Search in Google Scholar

Sathaye, S. D., Patil, K. R., Kulkarni, S. D., Bakre, P. P., Pradhan, S. D., Sarwade, B. D., & Shintre, S. N. (2003). Modification of spin coating method and its application to grow thin films of cobalt ferrite. Journal of Materials Science, 38, 29-33. DOI: 10.1023/a:1021101529855.Search in Google Scholar

Sceney, C. G., Hill, J. O., & Magee, R. J. (1975). Thermal analysis of copper dithiocarbamates. Thermochimica Acta, 11, 301-306. DOI: 10.1016/0040-6031(75)85099-4.Search in Google Scholar

Schubert, D. W., & Dunkel, T. (2003). Spin coating from a molecular point of view: its concentration regimes, influence of molar mass and distribution. Materials Research Innovations, 7, 314-321. DOI: 10.1007/s10019-003-0270-2.Search in Google Scholar

Sheldrick, G. M. (2008). A short history of SHELX. Acta Crystallographica Section A, 64, 112-122. DOI: 10.1107/s010876 7307043930.Search in Google Scholar

Singh, K. (1971). Magnetic and spectroscopic studies on cupric azide. Transactions of the Faraday Society, 67, 2436-2444. DOI: 10.1039/tf9716702436.Search in Google Scholar

Wang, J., Chen, J. T., Yuan, X. M., Wu, Z. G., Miao, B. B., & Yan, P. X. (2006). Copper nitride (Cu3N) thin films deposited by RF magnetron sputtering. Journal of Crystal Growth, 286, 407-412. DOI: 10.1016/j.jcrysgro.2005.10.107. Search in Google Scholar

Received: 2014-7-15
Revised: 2014-8-21
Accepted: 2014-8-22
Published Online: 2015-3-3
Published in Print: 2015-4-1

© 2015 Institute of Chemistry, Slovak Academy of Sciences

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