Abstract
A new Schiff base ligand derived from S-benzyldithiocarbazate and 4-[N-hydroxy ethyl-N-(methyl)amino]benzaldehyde (HL, where H is a dissociable proton) and its NiII, CuII, ZnII and PdII complexes were prepared and fully characterized. The structures of HL and Ni(L)2 were determined by X-ray diffraction analysis, which revealed that the geometry of the NiII ion is square-planar with two equivalent Ni=N and Ni=S bonds, and that the two neighboring molecules in two layers have weak contact. The electronic spectra and solution fluorescence of the ligand and the complexes were studied, and the quantum yields of single-photon fluorescence for the compounds were determined. The compounds possess two-photon absorption (t.p.a.) character and the t.p.a. coefficient β and t.p.a. cross-section σ were determined by the Z-scan technique. Especially, the Zn(L)2complex and the HL ligand exhibit intensive two-photon fluorescence (t.p.f.) at 800 nm laser pulses in the femtosecond regime.
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References
M. Goppert-Mayer, Ann. Phys. Lpz, 9, 273 (1931).
W. Kaiser and C. G. B. Garret, Phys. Rev. Lett., 7, 229 (1961).
(a)C. Wang, Y. Ren, Z. S. Shao, X. Zhao, G. Y. Zhou, D. Wang, Q. Fang and M. H. Jiang, J. Mod. Opt., 48, 1113 (2001). (b)X. J. Tang, L. Z. Wu, L. P. Zhang and C. H. Tung, Chem. Phys. Lett., 356, 573 (2002). (c)G. S. He, L. X. Yuan, Y. P. Cui, M. Li and P. N. Prasad, J. Appl. Phys., 81, 2529 (1997). (d)G. S. He, J. D. Bhawalkar, C. K. Park, C. F. Zhao, G. Ruland and P. N. Prasad, Appl. Phys. Lett., 68, 3549 (1996).
(a)C. W. Spangler, J. Mater. Chem., 9, 2013 (1999). (b)J. Oberle, L. Bramerie, G. Jonusanskas and C. Rulliere, Opt. Commun., 169, 325 (1999). (c)G. S. He, L. X. Yuan, N. Chang, J. D. Bhawalkar, P. N. Prasad, L. L. Brott, S. J. Clarson and B. A. Reinhardt, J. Opt. Soc. Am. B, 14, 1079 (1997). (d)H. Lei, H. Z. Wang, Z. C. Wei, X. J. Tang, L. Z. Wu, C. H. Tung and G. Y. Zhou, Chem. Phys. Lett., 333, 387 (2001).
(a)K. D. Belfield, K. J. Schafer, Y. Liu, X. B. Ren and E. W. V. Stryland, J. Phys. Org. Chem., 13, 837 (2000). (b)W. Denk, J. H. Strickler and W. W. Webb, Science, 248, 73 (1990). (c)R. H. Kohler, J. Cao, W. R. Zipfel, W. W. Webb and M. R. Hansen, Science, 276, 2039 (1997). (d)W. Denk, Proc. Natl. Acad. Sci. USA., 91, 6629 (1994).
(a)S. Kawata and Y. Kawata, Chem. Rev., 100, 1777 (2000). (b) D. A. Parthenopoulos and P. M. Rentzepis, Science, 245, 843 (1989). (c)H. E. Pudavar, M. P. Joshi, P. N. Prasad and B. A. Reinhardt, Appl. Phys. Lett., 74, 1338 (1999). (d)K. D. Bel eld, Y. Liu, R. A. Negres, M. Fan, G. Pan, D. J. Hagan and F. E. Hernandez, Chem. Mater., 14, 3663 (2002).
W. H. Zhou, S. M. Kuebler, K. L. Braun, T. Y. Yu, J. K. Cammack, C. K. Ober, J. W. Perry and S. R. Marder, Science, 296, 1106 (2002).
(a)B. H. Cumpston, S. P. Ananthavel, S. Barlow, D. L. Dyer, J. E. Ehrlieh, L. L. Erskine, A. A. Helkal, S. M. Kuebler, I. Y. S. Lee, D. McCord-Maughon, J. Q. Qin, H. Ro ¨ckel, M. Rumi, X. L. Wu, S. R. Marder and J. W. Perry, Nature, 398, 51 (1999). (b)S. Kawata, H. B. Sun, T. Tanaka and K. Takada, Nature, 412, 697 (2001). (c) T. J. Bunning, S. M. Kirkpatrick, L. V. Natarajan, V. P. Tondiglia and D. W. Tomlin, Chem. Mater., 12, 2842 (2000). (d)S. Maruo, O. Nakamura and S. Kawata, Opt. Lett., 22, 132 (1997). (e)M. P. Joshi, H. E. Pudavar, J. Swiatkiewicz, P. N. Prasad and B. A. Reianhardt, Appl. Phys. Lett., 74, 170 (1999).
(a)A. M. R. Fisher, A. L. Murphree and C. J. Gomer, Laser Surg. Med., 17, 2 (1995). (b)H. Stiel, K. Tenchner and A. Paul, J. Photochem. Photobiol. A:Chem., 80, 289 (1994). (c)P. K. Frederiksen, M. Jorgensen and P. R. Ogilby, J. Am. Chem. Soc., 123, 1215 (2001).
(a)M. Albota, D. Beljonne, J. L. Bredas, J. E. Ehrlich, J. Y. Fu, A. A. Heikal, S. E. Hess, T. Kogej, M. D. Levin, S. R. Marder, D. McCord-Maughon, J. W. Perry, H. Rockel, M. Rumi, G. Subramaniam, W. W. Webb, X. L. Wu and C. Xu, Science, 281, 1653 (1998). (b)M. Rumi, J. E. Ehrlich, A. A. Heikal, J. W. Perry, S. Barlow, Z. Y. Hu, D. McCord-Maughon, T. C. Parker, H. Rockel, S. Thayumanavan, S. R. Marder, D. Beljonne and J. L. Bredas, J. Am. Chem. Soc., 122, 9500 (2000). (c)D. W. Brousmiche, J. M. Serin, J. M. J.;Fre´chet, G. S. He, T. C. Lin, S. J. Chung and P. N. Prasad, J. Am. Chem. Soc., 125, 1448 (2003). (d)B. A. Reinhardt, L. L. Brott, S. J. Clarson, A. G. Dillard, J. C. Bhatt, R. Kannan, L. X. Yuan, G. S. He and P. N. Prasad, Chem. Mater., 10, 1863 (1998). (e)R. Kannan, G. S. He, L. X. Yuan, F. M. Xu, P. N. Prasad, A. G. Dombroskie, B. A. Reinhardt, J. W. Baur, R. A. Vaia and L. S. Tan, Chem. Mater., 13, 1896 (2001).
(a)Y. P. Tian, W. T. Yu, C. Y. Zhao and M. H. Jiang, Polyhedron, 21, 1217 (2002). (b)X. H. Zhu, X. F. Chen, Y. Zhang, X. Z. You, W. L. Tan, W. Ji, J. J. Vittal, G. K. Tan and H. L. Kennard, New J. Chem., 24, 419 (2000). (c)Z. H. Liu, C. Y. Duan, J. Hu and X. Z. You, Inorg. Chem., 38, 1719 (1999). (d)Y. P. Tian, Z. L. Lu and X. Z. You, Acta Chim. Sin., 57, 1068 (1999). (e)Y. P. Tian, C. Y. Duan and X. Z. You, Transition Met. Chem., 23, 17 (1998). (f)Y. P. Tian, C. Y. Duan, C. Y. Zhao, Z. L. Lu and X. Z. You, Inorg. Chem., 36, 1247 (1997). (g)C. Y. Duan, Y. P. Tian, X. Z. You and T. C. W. Mak, Polyhedron, 16, 4097 (1997).
Z. M. Xue, Y. P. Tian, D. Wang and M. H. Jiang, J. Chem. Soc. Dalton Trans., 1373 (2003).
(a)M. S. Bahae, A. A. Said, T. H. Wei, D. J. Hagan and W. V. Stryland, IEEE J. Quantum Electron, 26, 760 (1990). (b)J. Zhou, E. Y. B. Pun and X. H. Zhang, J. Opt. Soc. Am. B, 18, 1456 (2001). (c)C. Y. Tsai, S. P. Chen and T. C. Wen, Chem. Phys., 240, 191 (1999). (d)B. L. Yu, C. S. Zhu, F. X. Gang, H. B. Chen and Y. S. Huang, Acta Opt. Sin., 17, 423 (1997).
M. Akbar Ali and M. T. H. Tarafdar, J. Inorg. Nucl. Chem., 39, 1785 (1977).
M. Akbar Ali and R. Bose, J. Inorg. Nucl. Chem., 39, 265 (1977).
R. Mayer, in M. J. Janseen, (Ed.) Organosulphur Chemistry, Interscience, New York, 1967, p. 21.
B. A. Gingras and A. F. Sirianni, Can. J. Chem., 42, 17 (1964).
J. N. Demas and G. A. Crosby, J. Phys. Chem., 75, 991 (1971).
J. D. Bhawalkar, G. S. He and P. N. Prasad, Rep. Prog. Phys., 59, 1041 (1996).
(a)G. S. He, G. C. Xu, P. N. Prasad, B. A. Reinhardt, J. C. Bhatt and A. G. Dillard, Opt. Lett., 20, 435 (1995). (b)G. S. He, J. Swiatkiewicz, Y. Jiang and P. N. Prasad, J. Phys. Chem. A, 104, 4805 (2000). (c)G. Y. Zhou, X. M. Wang, D. Wang, C. Wang, Z. S. Shao, Q. Fang and M. H. Jiang, Opt. Commun., 190, 345 (2001).
J. L. Bradas, C. Adant, P. Tackx, A. Persoons and B. M. Pierce, Chem. Rev., 94, 243 (1994).
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Zhang, ML., Tian, YP., Zhang, XJ. et al. Synthesis, crystal structure and two-photon property studies on a series of complexes derived from a novel Schiff base ligand. Transition Metal Chemistry 29, 596–602 (2004). https://doi.org/10.1007/s11243-004-1208-2
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DOI: https://doi.org/10.1007/s11243-004-1208-2