Abstract
The effect of the nature of organic ligands and complex formation on the photoluminescent characteristics (relative quantum yield, excited-state lifetime) and thermal stability of tetradentate Schiff bases (H2L), derivatives of salicylaldehyde (H2(SAL)1, H2(SAL)2), o-vanillin (H2(MO)1, H2(MO)2) with ethylenediamine and o-phenylenediamine, and their zinc(II) complexes was studied. Zinc(II) complexes were synthesized by the reaction of H2L with Zn(AcO)2·2H2O in MeOH at room temperature or under reflux. In the case of H2L = H2(SAL)2, H2(MO)1, H2(MO)2, complexes of the composition ZnL·H2O were isolated irrespective of the temperature. For H2L = H2(SAL)1, the reaction results in Zn(SAL)1·H2O at room temperature and in anhydrous dimeric complex [Zn(SAL)1]2 under reflux. Density functional calculations of H2L and ZnL confirmed that (1) luminescence of these compounds is due to the π-π* transition between orbitals of the organic ligand and (2) enhancement of conjugation of the chain and introduction of electron-donating substituents lead to a decrease of the energy gap and, there-fore, to a bathochromic shift of the emission maximum.
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H. Tanaka, S. Tokito, Y. Taga, A. Okada, J. Mater. Chem., 1998, 8, 1999.
S. Wang, Coord. Chem. Rev., 2001, 251, 79.
R. C. Evans, P. Douglas, C. J. Winscom, Coord. Chem. Rev., 2006, 250, 2093.
A. V. Metelitsa, A. S. Burlov, S. O. Bezuglyi, I. G. Borodkina, V. A. Bren’, A. D. Garnovskii, V. I. Minkin, Coordinats. Khim., 2006, 32, 894 [Russ. J. Coord. Chem., 2006, 32, 858 (Engl. Transl.)].
S.-L. Zheng, X.-M. Chen, Aust. J. Chem., 2004, 57, 703.
S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, H.-E. Lee, C. Adachi, P. E. Burrows, S. R. Forrest, M. E. Thompson, J. Am. Chem. Soc., 2001, 123, 4304.
Y. W. Shi, M.-M. Shi, J.-C. Huang, H.-Z. Chen, M. Wang, X.-D. Liu, Y.-G. Ma, H. Xu, B. Yang, Chem. Commun., 2006, 1941.
C. Pérez-Bolivar, V. A. Montes, P. Anzenbacher, Inorg. Chem., 2006, 45, 9610.
R. Pohl, P. Anzenbacher, Org. Lett., 2003, 5, 2769.
S. Mizukami, H. Houjou, K. Sugaya, E. Koyama, H. Tokuhisa, T. Sasaki, M. Kanesato, Chem. Mater., 2005, 17, 50.
M. E. Germain, T. R. Vargo, P. G. Khalifah, M. J. Knapp, Inorg. Chem., 2007, 46, 4422.
W.-K. Lo, W.-K. Wong, W.-Y. Wong, J. Guo, K.-T. Yeung, Y.-K. Cheng, X. Yang, R. A. Jones, Inorg. Chem., 2006, 45, 9315.
V. Coropceanu, J. Cornil, D. A. da Silva Filho, Y. Olivier, R. Silbey, J.-L. Brédas, Chem. Rev., 2007, 107, 926; Y. Shirota, H. Kageyama, Chem. Rev., 2007, 107, 953.
P. G. Gozzi, L. S. Dolci, A. Garelli, M. Montalti, L. Prodi, N. Zaccheroni, New. J. Chem., 2003, 27, 692.
T. Sano, Y. Nishio, Y. Hamada, H. Takahash, T. Usuki, K. Shibata, J. Mater. Chem., 2000, 10, 157.
S. H. Hwang, P. Wang, C. N. Moorefield, J.-Che. Jung, J.-Y. Kim, S.-W. Lee, G. R. Newkome, Macromol. Rapid Commun., 2006, 27, 1809.
N. Yoshida, K. Ichikawa, M. Shiro, J. Chem. Soc., Perkin Trans., 2000, 2, 17.
W. Lu, M. C. W. Chen, K.-K. Cheung, Ch.-M. Che, Organometallics, 2001, 20, 2477.
H. Schiff, Ann. Suppl., 1864, 3, 43.
M. J. O’Conner, B. O. West, Aust. J. Chem., 1967, 20, 2077.
G. E. Bately, D. P. Graddon, Aust. J. Chem., 1967, 20, 885.
C. de Mello Donegá, S. A. Junior, G. F. de Sa, Chem. Commun., 1996, 1199.
C. Lee, W. Yang, R. G. Parr, Phys. Rev. B, 1988, 37, 785.
P. J. Hay, W. R. Wadt, J. Chem. Phys., 1985, 82, 270.
V. Bertolasi, P. Gilli, V. Ferretti, G. Gilli, J. Am. Chem. Soc., 1991, 113, 4917.
P. Gilli, V. Bertolasi, V. Ferretti, G. Gilli, J. Am. Chem. Soc., 2000, 122, 1045.
D. Hall, F. H. Moore, J. Chem. Soc. (A), 1966, 1822.
M. Odoko, N. Tsuchida, N. Okabe, Acta Crystallogr., 2006, E62, m708.
A. de Bettencourt-Dias, Dalton Trans., 2007, 2229.
W.-Y. Wong, G.-L. Lu, L. Liu, J.-X. Shi, J. Lin, Eur. J. Inorg. Chem., 2004, 2066.
S.-L. Zheng, J.-P. Zhang, X.-M. Chen, Z.-L. Huang, Z.-Y. Lin, W.-T. Wong, Chem. Eur. J., 2003, 9, 3888.
T. Sekikawa, T. Kobayashi, T. Inabe, J. Phys. Chem. B, 1997, 101, 10645.
H. Joshi, F. S. Kamounah, C. Gooijer, G. Van der Zwan, L. Antonor, J. Photochem. Photobiol. A: Chem., 2002, 152, 183.
M. Ziółek, J. Kubicki, A. Maciejewski, R. Nasręcki, A. Grabowska, Chem. Phys. Lett., 2003, 369, 80.
K. Amimoto, T. Kawato, J. Photochem. Photobiol. C: Photochem. Rev., 2005, 6, 207.
D. LeGourriérec, V. A. Kharlanov, R. G. Brown, W. Rettig, J. Photochem. Photobiol. A: Chem., 2000, 130, 101.
K. Ueno, A. E. Martell, J. Phys. Chem., 1956, 60, 1270.
A. Filarowski, J. Phys. Org. Chem., 2005, 18, 686.
F. Liang, J. Chen, Y. Cheng, L. Wang, D. Ma, X. Jing, F. Wang, J. Mater. Chem., 2003, 13, 1392.
S.-M. Yue, H.-B. Xu, J.-F. Ma, Z.-M. Su, Y.-H. Kan, H.-J. Zhang, Polyhedron, 2006, 25, 635.
Y.-P. Tong, S.-L. Zheng, X.-M. Chen, J. Mol. Struct., 2007, 826, 104.
Y.-P. Tong, S.-L. Zheng, X.-M. Chen, Inorg. Chem., 2005, 44, 4270.
Y.-P. Tong, S.-L. Zheng, X.-M. Chen, Eur. J. Inorg. Chem., 2005, 3734.
S.-L. Zheng, J.-H. Yang, X.-L. Yu, X.-M. Chen, W.-T. Wong, Inorg. Chem., 2004, 43, 830.
D. Cunningham, K. Giligan, M. Hannon, C. Kelly, P. McArdle, A. O’Malley, Organometallics, 2004, 23, 984.
M. E. Germain, T. R. Vargo, P. G. Khalifah, M. J. Knapp, Inorg. Chem., 2007, 46, 4422.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1846–1855, September, 2008.
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Kotova, O.V., Eliseeva, S.V., Averjushkin, A.S. et al. Zinc(II) complexes with Schiff bases derived from ethylenediamine and salicylaldehyde: the synthesis and photoluminescent properties. Russ Chem Bull 57, 1880–1889 (2008). https://doi.org/10.1007/s11172-008-0254-x
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DOI: https://doi.org/10.1007/s11172-008-0254-x