Abstract
This study includes the synthesis, characterization, electrochemical analysis and photoluminescence properties of a Schiff base ligand bearing a pyrimidine ring and its Co(II), Ni(II), Cu(II) and Pd(II) metal complexes. The Schiff base ligand was derived from the condensation reaction of a pyrimidine amine with 2-hydroxy-1-naphthaldehyde. The structures were characterized using FT-IR, UV–Vis, elemental analysis, magnetic susceptibility and electrolytic conductivity. The ligand and its metal complexes displayed strong violet emissions upon UV exposure. The photoluminescence quantum yield and excited-state decay were measured for the ligand and its complexes. The excited-state lifetime for the ligand was 3.70 ns and its quantum yield of luminescence was found to be 0.40. A reduction in photoluminescence intensity and quantum yield was observed upon metal ion complexation. The compounds synthesized were studied by cyclic voltammetry to probe the existence of electrochemical reduction and oxidation processes.
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R. Hernández-Molina, A. Mederos, in Comprehensive Coordination Chemistry II, vol. 1, ed. by J.A. McCleverty, T.J. Meyer (Elsevier, Amsterdam, 2004), p. 411
M. Andruh, F. Tuna, in Focus on Organometallic Chemistry Research, ed. by M.A. Cato (Nova Publishers, Hauppauge, 2005), p. 144
A.J. Atkins, D. Black, A.J. Blake, A. Marin-Bocerra, S. Parsons, L. Ruiz-Ramirez, M. Schröder, Chem. Commun. 4, 457 (1996)
P.A. Vigato, S. Tamburini, Coord. Chem. Rev. 248, 1717 (2004)
P.A. Vigato, S. Tamburini, L. Bertolo, Coord. Chem. Rev. 251, 1311 (2007)
M. Sakamoto, K. Maneski, H. Okawa, Coord. Chem. Rev. 219–221, 379 (2001)
G. Ceyhan, C. Celik, S. Urus, I. Demirtas, M. Elmastas, M. Tümer, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 81(1), 184 (2011)
R. Herchel, I. Nemec, M. Machata, Z. Trávníček, Inorg. Chem. 54(17), 8625 (2015)
N.S. Youssef, E.A. El-Zahany, M.A. El-Seidy, J. Phosphorus Sulfur Silicon Relat. Elem. 185(4), 785 (2010)
N.K. Chaudhary, P. Mishra, Bioinorg. Chem. Appl. 2017, 1 (2017)
R. Herchel, I. Nemec, M. Machata, Z. Trávníček, J. Sep. Sci. Technol. 52(6), 1052 (2017)
A.D. Garnovskii, A.L. Nivorozhkin, V.I. Minkin, Coord. Chem. Rev. 126, 1 (1993)
M. Valcarcel, M.D. Laque de Castro, Flow-Throgh Biochemical Sensors (Elsevier, Amsterdam, 1994)
U. Spichiger-Kelle, Chemical Sensors and Biosensors for Medical and Biological Applications (Wiley, Weinheim, 1998)
J.F. Lawrence, R.W. Frei, Chemical Derivatization in Chromatography (Elsevier, Amsterdam, 1976)
M. Sönmez, M. Çelebi, I. Berber, Eur. J. Med. Chem. 45, 1935 (2010)
J.I. Pyo, E.J. Hwang, C.S. Cheong, S.H. Lee, S.W. Lee, I.T. Kim, S.H. Lee, Synth. Met. 155, 461 (2005)
H. Lee, J. Oh, H.Y. Chu, J.-I. Lee, S.H. Kim, Y.S. Yang, G.H. Kim, L.M. Do, T. Zyung, J. Lee, Y. Park, Tetrahedron 59, 2773 (2003)
K.W. Xue, B.Y. Chen, G.G. Han, Y. Duan, P. Chen, Y.Q. Yang, Y.H. Duan, X. Wang, Y. Zhao, Org. Electron. 22, 122 (2015)
J.Y. Song, S.N. Park, S.J. Lee, Y.K. Kim, S.S. Yoon, Dyes Pigment 114, 40 (2015)
T. Yu, W. Su, W. Li, Z. Hong, R. Hua, M. Li, B. Chu, B. Li, Z. Zhang, Z.Z. Hu, Inorg. Chim. Acta 359, 2246 (2006)
T. Yu, W. Su, W. Li, Z. Hong, R. Hua, B. Li, Thin Solid Films 515, 4080 (2007)
T. Yu, W. Su, W. Li, Z. Hong, R. Hua, M. Li, B. Chu, B. Li, Z. Zhang, Z.Z. Hu, Chem. Soc. Rev. 39, 189 (2010)
V. Nishal, D. Singh, A. Kumar, V. Tanwar, I. Singh, R. Srivastava, P.S. Kadyan, J. Org. Semicond. 2, 15 (2014)
V.B. Nagaveni, K.M. Mahadevan, G.R. Vijayakumar, H. Nagabhushana, S. Naveen, N.K. Lokanath, J. Sci. Adv. Mater. Dev. 3, 51 (2018)
C. Maxim, T.D. Pasatoiu, VCh. Kravtsov, S. Shova, C.A. Muryn, R.E.P. Winpenny, F. Tuna, M. Andruh, Inorg. Chim. Acta 361, 3903 (2008)
M. Köse, G. Ceyhan, M. Tümer, I. Demirtas, I. Gönül, V. McKee, Spectrochim. Acta A 137, 477 (2015)
J. Chakraborty, S. Thakurta, G. Pilet, R.F. Ziessel, L.J. Charbonnière, S. Mitra, Eur. J. Inorg. Chem. 26, 3993 (2009)
L. He, L. Duan, J. Qiao, D. Zhang, G. Dong, L. Wang, Y. Qiu, Org. Electron. 10, 152 (2009)
D. Sek, M. Siwy, K. Bijak, M. Filapek, G. Malecki, E.M. Nowak, J. Electroanal. Chem. 751, 128 (2015)
Y. Niko, Y. Hiroshige, S. Kawauchi, G. Konishi, Tetrahedron 68, 6177 (2012)
A. Gilbert, J. Bagott, Essentials of Molecular Photochemistry (CRC Press Boca Raton Inc., Florida, 1991)
H. Ishida, S. Tobita, Y. Hasegawa, R. Katoh, K. Nozaki, Coord. Chem. Rev. 254, 2449 (2010)
E. Sarıpınar, C. Yılmaz, D. Unal, I.O. Ilhan, N. Yazır, Y. Akcamur, Hetero Cycles 68, 2045 (2006)
Ü. Ceylan, M.E. Hacıyusufoğlu, S.P. Yalçın, M. Sönmez, M. Aygün, J. Mol. Struct. 1109, 209 (2016)
A. Gencer Imer, R.H.B. Syan, M. Gülcan, Y.S. Ocak, A. Tombak, J. Mater. Sci.: Mater. Electron. 29, 898 (2017)
V.P. Singh, S. Singh, D.P. Singh, K. Tiwari, M. Mishra, J. Mol. Struct. 1058, 71 (2014)
M. Gülcan, M. Sönmez, I. Berber, Turk. J. Chem. 36, 189 (2012)
M. Sönmez, M.E. Hacıyusufoğlu, Asian J. Chem. 18, 2032 (2006)
M. Sönmez, M. Çelebi, A. Levent, I. Berber, Z. Şentürk, J. Coord. Chem. 63, 848 (2010)
S. Ilhan, H.M. Baykara, S. Seyitoglu, A. Levent, S. Özdemir, A. Dündar, A. Öztomsuk, M.H. Cornejo, J. Mol. Struct. 1075, 32 (2014)
P. Zanello, Inorganic Electrochemistry; Theory, Practice and Application (The Royal Society of Chemistry, London, 2003)
M. Aguilar-Martinez, R. Saloma-Aguila, N. Macias-Ruvalcaba, R. Cetina-Rosado, A. Navarrete-Vazquez, V. Gomez-Vidales, A. Zantella-Dehesa, R.A. Toscano, S. Hernandez-Ortega, G.J.J. Fernandez, J. Chem. Soc., Dalton Trans. 16, 2327 (2001)
H. Kılıç, M. Berkem, J. Serb. Chem. Soc. 69, 689 (2004)
M. Sönmez, M. Çelebi, A. Levent, I. Berber, Z. Şentürk, J. Coord. Chem. 63, 1986 (2010)
S. Yaqiu, Y. Guangming, L. Daizheng, J. Zonghui, Y. Shiping, C. Peng, J. Mol. Struct. 842, 55 (2007)
H. Liu, F.X. Li, Y. Pi, D.J. Wang, Y.J. Hu, J. Zheng, Spectrochim. Acta A 145, 588 (2015)
M.K. Paul, Y.D. Singh, N.B. Singh, U. Sarkar, J. Mol. Struct. 1081, 316 (2015)
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Sönmez, M., Hacıyusufoğlu, M.E., Levent, A. et al. Synthesis of pyrimidine Schiff base transition metal complexes: characterization, spectral and electrochemical analyses, and photoluminescence properties. Res Chem Intermed 44, 5531–5546 (2018). https://doi.org/10.1007/s11164-018-3438-5
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DOI: https://doi.org/10.1007/s11164-018-3438-5