Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization, Catalytic Applications and Optical Sensing Properties of Palladium Complexes Containing Tetradentate Schiff Bases
Corresponding Author(s) : P. Köse Yaman
Asian Journal of Chemistry,
Vol. 26 No. 12 (2014): Vol 26 Issue 12
Abstract
In this study, the synthesis, spectroscopic and catalytic properties of PdLn (n = 1-6) complexes with tetradentate -ONNO- and -SNNS- type Schiff base ligands LnH2 (n = 1-6) were investigated. The PdLn (n = 1-6) complexes were synthesized by the thermal reactions of the Schiff bases and Pd(OAc)2 in acetonitrile and characterized by elemental analysis, FT-IR, 1H NMR, UV-visible and TGA/DTG. The spectroscopic studies suggest that all of the ligands are coordinated to the central metal as a tetradentate ligand coordinating via the central azomethine nitrogens (C=N) and phenolic oxygen/sulfur atoms. On the palladium-catalyzed Suzuki cross-coupling reactions employing PdLn (n = 1-6) complexes toward a various substituted arylbromides and boronic acids were pursued. The conversions were obtained and yields with different arylbromides were calculated and discussed. All the complexes were thermally stable and were not sensitive to air or the moisture. The complexes were easily prepared from low cost precursors that could be used as versatile and catalysts for different C-C coupling reactions (Suzuki-Miyaura reactions). Moreover steady state fluorescence emission and excitation spectra were measured. These studies have been shown that PdL2 and PdL3 dyes exhibited high fluorescence intensity and selective and efficient response to cobalt ions over other metal ions in buffered solutions.
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References
R.H. Holm and M.J. O’Connor, Prog. Inorg. Chem., 14, 325 (1971).
J. Costamagna, J. Vargas, R. Latorre, A. Alvarado and G. Mena, Coord. Chem. Rev., 119, 67 (1992); doi:10.1016/0010-8545(92)80030-U.
E. Tas, A. Kilic, N. Konak and I. Yilmaz, Polyhedron, 27, 1024 (2008); doi:10.1016/j.poly.2007.11.038.
A. Kilic, E. Tas, B. Deveci and I. Yilmaz, Polyhedron, 26, 4009 (2007); doi:10.1016/j.poly.2007.05.013.
(a) S. Yamada, Coord. Chem. Rev., 190-192, 537 (1999); doi:10.1016/S0010-8545(99)00099-5. (b) D.E. Fenton, Chem. Soc. Rev., 28, 159 (1999); doi:10.1039/a805645e.
L. Canali and D.C. Sherrington, Chem. Soc. Rev., 28, 85 (1999); doi:10.1039/a806483k.
Y. Suzuki, H. Terao and T. Fujita, Bull. Chem. Soc. Jpn., 76, 1493 (2003); doi:10.1246/bcsj.76.1493.
J.A. Stubbe and W.A. van der Donk, Chem. Rev., 98, 705 (1998); doi:10.1021/cr9400875.
D.A. Atwood and M.J. Harvey, Chem. Rev., 101, 37 (2001); doi:10.1021/cr990008v.
R. Ziessel, Coord. Chem. Rev., 216-217, 195 (2001); doi:10.1016/S0010-8545(00)00410-0.
K.C. Gupta and A.K. Sutar, J. Mol. Catal. Chem., 272, 64 (2007); doi:10.1016/j.molcata.2007.03.025.
S.R. Collinson and D.E. Fenton, Coord. Chem. Rev., 148, 19 (1996); doi:10.1016/0010-8545(95)01156-0.
S. Akine and T. Nabeshima, Dalton Trans., 10395 (2009); doi:10.1039/B910989G.
H. Temel, J. Coord. Chem., 57, 723 (2004); doi:10.1080/00958970410001721024.
H. Temel, S. İlhan, M. Şekerci and R. Ziyadanogullari, Spectrosc. Lett., 35, 219 (2002); doi:10.1081/SL-120003807.
H. Temel, S. Ilhan and M. Sekerci, Synth. React. Inorg. Met-Org. Chem., 32, 1625 (2002); doi:10.1081/SIM-120015083.
H. Temel, U. Cakir, H.I. Ugras and M. Sekerci, J. Coord. Chem., 56, 943 (2003); doi:10.1080/0095897031000135324.
E. Tas, M. Aslanoglu, M. Ulusoy and H. Temel, J. Coord. Chem., 57, 77 (2004).
H. Temel, B. Ziyadanogullari, I. Aydin and F. Aydin, J. Coord. Chem., 58, 1177 (2005); doi:10.1080/00958970500078890.
H. Temel and M. Sekerci, Synth. React. Inorg. Met-Org. Chem., 31, 849 (2001); doi:10.1081/SIM-100104855.
H. Temel, Ü. Çakir and H. İbrahim Uğraş, Synth. React. Inorg. Met-Org. Chem., 34, 819 (2004); doi:10.1081/SIM-120035960.
A. Burkhardt, H. Görls and W. Plass, Carbohydr. Res., 343, 1266 (2008); doi:10.1016/j.carres.2008.01.039.
M.K. Taylor, K.D. Trotter, J. Reglinski, L.E.A. Berlouis, A.R. Kennedy, C.M. Spickett and R.J. Sowden, Inorg. Chim. Acta, 361, 2851 (2008); doi:10.1016/j.ica.2008.02.021.
S. Burling, M.K. Whittlesey and J.M.J. Williams, Adv. Synth. Catal., 347, 591 (2005); doi:10.1002/adsc.200404308.
L. Botella and C. Najera, Angew. Chem. Int. Ed., 41, 179 (2002); doi:10.1002/1521-3773(20020104)41:1<179::AID-ANIE179>3.0.CO;2-O.
A. Suzuki, J. Organomet. Chem., 576, 147 (1999); doi:10.1016/S0022-328X(98)01055-9.
N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995); doi:10.1021/cr00039a007.
S. Haber and H.J. Kleiner (Hoescht AG) DE 19527118, Chem. Abstr., 126, 185894 (1997).
D.D. Perrin, W.L.F. Armarego and D.R. Perrin, Purification of Laboratory Chemicals, Oxford: Pergamon, edn 2 (1980).
A. Elmali and Y. Elerman, J. Mol. Struct., 737, 29 (2005); doi:10.1016/j.molstruc.2004.10.007.
(a) I. Yilmaz, H. Temel and H. Alp, Polyhedron, 27, 125 (2008); doi:10.1016/j.poly.2007.08.044.; (b) H. Temel, H. Alp, S. Ilhan and B. Ziyadanogullari, J. Coord. Chem., 61, 1146 (2008); doi:10.1080/00958970701502334.
H. Temel, H. Alp, S. Ilhan, B. Ziyadanogullari and I. Yilmaz, Monatsh. Chem., 138, 1199 (2007); doi:10.1007/s00706-007-0713-3.
G. Schetty and E. Steiner, Helv. Chim. Acta, 57, 2149 (1974); doi:10.1002/hlca.19740570731.
R.L. Lintvedt, K.A. Rupp and M.J. Heeg, Inorg. Chem., 27, 331 (1988); doi:10.1021/ic00275a021.
B. Crociani, M. Sala, A. Polo and G. Bombieri, Organometallics, 5, 1369 (1986); doi:10.1021/om00138a012.
V.T. Kasumov, E. Tas, F. Koksal and S. Ozalp-Yaman, Polyhedron, 24, 319 (2005); doi:10.1016/j.poly.2004.11.020.
K. Naresh Kumar and R. Ramesh, Polyhedron, 24, 1885 (2005); doi:10.1016/j.poly.2005.05.020.
E. Tas, M. Aslanoglu, A. Kilic, O. Kaplana and H. Temel, J. Chem. Res. (S), 2006, 242 (2006); doi:10.3184/030823406776894292.
M. Ulusoy, O. Sahin, O. Buyukgungor and B. Cetinkaya, J. Organomet. Chem., 693, 1895 (2008); doi:10.1016/j.jorganchem.2008.02.017.
L. Sacconi, M. Ciampolini, F. Maggio and F.P. Cavasino, J. Am. Chem. Soc., 84, 3246 (1962); doi:10.1021/ja00876a005.
R.L. Carlin, Transition Metal Chemistry, Marcel Dekker, New York, Vol. 1 (1965).
C. Fraser and B. Bosnich, Inorg. Chem., 33, 338 (1994); doi:10.1021/ic00080a024.
H. Köksal, M. Dolaz, M. Tümer and S. Serin, Synth. React. Inorg. Met-Org. Chem., 31, 1141 (2001); doi:10.1081/SIM-100106854.
D.X. West, C.S. Carlson, A.E. Liberta and J.P. Scovill, Transition Met. Chem., 15, 383 (1990); doi:10.1007/BF01177467.
D.X. West, M.A. Lockwood, A.E. Liberta, X. Chen and R.D. Willett, Transition Met. Chem., 18, 221 (1993); doi:10.1007/BF00139960.
A.L. El-Ansary, A.A. Soliman, O.E. Sherif and J.A. Ezzat, Synth. React. Inorg. Met. Org. Chem, 32, 1301 (2002); doi:10.1081/SIM-120014307.
A.A. Soliman, J. Therm. Anal. Calorim., 63, 221 (2000); doi:10.1023/A:1010109125051.
A.A. Soliman, S.A. Ali, M.M.H. Khalil and R.M. Ramadan, Thermochim. Acta, 359, 37 (2000); doi:10.1016/S0040-6031(00)00486-X.
C. Baillie and J. Xiao, Tetrahedron, 60, 4159 (2004); doi:10.1016/j.tet.2004.03.058.
A.F. Littke and G.C. Fu, Angew. Chem. Int. Ed., 41, 4176 (2002); doi:10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U.
S. Demir, I. Ozdemir and B. Cetinkaya, Appl. Organomet. Chem., 20, 254 (2006); doi:10.1002/aoc.1039.
G. Altenhoff, R. Goddard, C.W. Lehmann and F. Glorius, J. Am. Chem. Soc., 126, 15195 (2004); doi:10.1021/ja045349r.