Abstract
Copper complexes (2a-Cu and 2b-Cu) having two amino groups were prepared from p-aminobenzoylacetone (1a) and 1-(4-aminophenyl)nonane-1,3-dione (1b) with copper(II) acetate, respectively. A soluble poly(azomethine) having β-diketonato copper(II) complex in the main chain was prepared by the polycondensation of 2b-Cu with terephthalaldehyde (3) in dimethyl sulfoxide (DMSO) at room temperature with H2SO4 as catalyst. After reprecipitation into methanol, a green product was obtained in 56% yield. The complex (5b-Cu) was soluble in common organic solvents such as CHCl3, tetrahydrofuran (THF), and DMSO. The number-average molecular weight (Mn) and molecular weight distribution of 5b-Cu determined by GPC were Mn=3500 (polystyrene standard) and Mw/Mn=1.71, respectively. The structure of 5b-Cu was supported by IR and elemental analysis. Thermogravimetric analysis (TGA) for 5b-Cu showed 5% weight loss at 250°C under nitrogen. Electrochemical data as well as absorption spectra of 5b-Cu in comparison with that of copper(II) bis[p-(1-aza-2-phenylethenyl)benzoylacetonate] (6) as a model compound show that the metal centers of the multinuclear complexes may be considered nearly independent of one another.
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P. W. Wojtkowski, Macromolecules, 20, 740 (1987).
P. W. Morgan, S. L. Kwolek, and T. C. Pletcher, Macromolecules, 20, 729 (1987).
K. Naka, A. Azuma, and Y. Chujo, Macromol. Rapid Commun., 19, 523 (1998).
W. Li and M. Wan, J. Appl. Polym. Sci., 62, 941 (1996).
S.-B. Park, H. Kim, W.-C. Z., and J. C. Jung, Macromolecules, 26, 1627 (1993).
H. Kim and W.-C. Zin, Polym. Bull., 39, 701 (1997).
O. Thomas, O. Inganäs, and M. R. Andersson, Macromolecules, 31, 2676 (1998).
K.-S. Lee and J. C. Won, Makromol. Chem., 190, 1547 (1989).
S. C. Rasmussen, D. W. Thompson, V. Singh, and J. D. Petersen, Inorg. Chem., 35, 3449 (1996).
I. Manners, Angew. Chem. Int. Ed. Engl., 35, 1602 (1996).
M. Rehahn, Acta Polym., 49, 201 (1998).
R. D. Archer, A. Lauterbach, and V. O. Ochaya, Polyhedron, 13, 2043 (1994).
H. S. Munro, P. Finocchiaro, A. Mamo, and A. Recca, Polym. Commun., 27, 202 (1986).
K. Hanabusa, T. Isogai, T. Koyama, and H. Shirai, Makromol. Chem., 194, 197 (1993).
R. D.G. Jones and L. F. Power, Aust. J. Chem., 24, 735 (1971).
M. E. B. Jones, M. F. Lynch, D. A. Thornton, and R. F. Webb, Makromol. Chem., 50, 232 (1961).
J. F. Wolfe, C. J. Eby, and C. R. Hauser, J. Org. Chem., 30, 55 (1965).
H. Imai, T. Shiraiwa, and M. Oiwa, Nippon Kagaku Kaishi, 1081 (1977).
H. Imai and T. Shiraiwa, Nippon Kagaku Kaishi, 208 (1979).
F. D. Lewis, A. M. Miller, and G. D. Salvi, Inorg. Chem., 34, 3173 (1995).
K.-S. Lee, J. C. Won, and J. C. Jung, Makromol. Chem., 190, 1547 (1989).
F. D. Lewis, A. M. Miller, and G. D. Salvi, Inorg. Chem., 34, 3173 (1995).
C. Tsiamis, P. D. Jannakoudark, N. Sachsinger, and H. Hennig, Electrochimica Acta, 38, 2623 (1993).
D. E. Fenton and R. L. Lintvedt, Inorg. Chem., 100, 6367 (1978).
R. Knapp, A. Schott, and M. Rehahn, Macromolecules, 29, 478 (1996).
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Naka, K., Horii, E. & Chujo, Y. Preparation of Soluble Poly(azomethine)s Having the β-Diketonate Metal Complex in the Main Chain. Polym J 32, 316–320 (2000). https://doi.org/10.1295/polymj.32.316
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DOI: https://doi.org/10.1295/polymj.32.316