Metal Complexes of π-expanded Ligand (5): Synthesis, Structural, and Photophysical Characterizations of Green-Red Luminescent Pyrene-based Salicylaldiminato-type Zinc Complexes
Main Article Content
Abstract
A series of pyrene-based salicylaldimine-type ligands containing n-octyl or cyclohexyl or phenyl groups at imine nitrogen group, 1-hydroxy-2-[(N-substituted-imino)methyl]-pyrenes (octyl 1, cyclohexyl 1b and phenyl 1c), were synthesized and characterized. The ligands reacting with zinc acetate in the presence of sodium acetate gave the bis(salicylaldiminato)-type Zn(II) complexes, [bis[2-[(N-substituted-imino)methyl]-1-pyrenolato-N,O] zinc(II)] (octyl 1(Zn), cyclohexyl 1b(Zn), phenyl 1c(Zn)). The new ligands and complexes were characterized by 1H NMR, IR spectroscopy, mass spectroscopy, elemental analysis, UV-vis spectroscopy, fluorescence spectroscopy, and X-ray diffraction. The influence of the π-extended conjugation of the pyrene-based salicylaldiminato-type ligands coordinated to Zn2+ greatly induces red-shift of the complexes 1(Zn), 1b(Zn) and 1c(Zn) in absorption and emission spectra. These results were confirmed by density-functional theory (DFT) and time-dependent DFT (TDDFT) molecular orbital calculations. Moreover, single crystal structure of simple salicylaldiminato Zn(II) complex 1’b(Zn) was compared to that of the corresponding pyrene-type salicylaldiminato complex 1b(Zn).
Keywords:
Coordination chemistry, Zinc complex, Pyrene, π-Expanded ligand, Salicylaldimine
References
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[3] S. D. Bella, I. P. Oliveri, A. Colombo, C. Dragonetti, S. Righetto, D. Roberto, An Unprecedented Switching of the Second-Order Nonlinear Optical Response in Aggregate Bis(Salicylaldiminato)Zinc(Ii) Schiff-Base Complexes, Dalton Trans., Vol. 41, 2012, pp. 7013-7016. https://doi.org/10.1039/C2DT30702B.
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[5] C. S. B. Gomes, P. T. Gomes, M. T. Duarte, R. E. D. Paolo, A. L. Macanita, M. J. Calhorda, Synthesis, Structure, and Photophysical Characterization of Blue-Green Luminescent Zinc Complexes Containing 2-Iminophenanthropyrrolyl Ligands, Inorg. Chem., Vol. 48, 2009, pp. 11176-11186. https://doi.org/-10.1021/ic9015-19s.
[6] L. Shi, R. Q. Fang, J. Y. Xue, Z. P. Xiao, S.-H. Tan, H. L. Zhu, Synthesis, Characterization, and Antibacterial and Cytotoxic Study of Metal Complexes with Schiff Base Ligands, Australian Journal of Chemistry, Vol. 61, No. 4, 2008, pp. 288-296. https://doi.org/10.1071/-CH07408.
[7] L. Li, C. S. B. Gomes, P. T. Gomes, M. T. Duarte, Z. Fan, New Tetradentate N,N,N,N-Chelating Α-Diimine Ligands and Their Corresponding Zinc and Nickel Complexes: Synthesis, Characterisation and Testing as Olefin Polymerisation Catalysts, Dalton Trans., Vol. 40, 2001, pp. 3365-3380.
https://doi.org/10.1039/C0DT01308K.
[8] L. Chen, J. Qiao, J. Xie, L. Duan, D. Zhang, L. Wang, Y. Qiu, Substituted azomethine–zinc complexes: Thermal Stability, Photophysical, Electrochemical and Electron Transport Properties, Inorganica Chimica Acta, Vol. 362, 2009, pp. 2327-2333.
https://doi.org/10.1016/j.ica.2008.10.016.
[9] M. G. Kaplunov, I. K. Yakushchenko, S. S. Krasnikova, S. N. Shamaev, A. P. Pivovarov, O. N. Efimov, New Electroluminescent Materials Based on Chelate Zinc Complexes, Russian Chemical Bulletin, Vol. 53, 2004, pp. 2148-2151. https://doi.org/10.1007/s11172-005-0088-8.
[10] M. E. Germain, T. R. Vargo, P. G. Khalifah, M. J. Knapp, Fluorescent Detection of Nitroaromatics and 2,3-Dimethyl- 2,3-dinitrobutane (DMNB) by a Zinc Complex: (salophen)Zn, Inorg. Chem., Vol. 46, 2007, pp. 4422-4429. https://doi.org/10.1021/ic062012c.
[11] M. A. Torzilli, S. Colquhoun, D. Doucet, R. H. Beer, The Interconversion of Dichlorobis(N-n-propylsalicylaldimine)zinc(II) and Bis(N-n-propylsalicylaldiminato)zinc(II) Polyhedron, Vol. 21, 2002, pp. 697-704.
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[13] I. P. Oliveri, S. Failla, A. Colombo, C. Dragonetti, S. Righetto, S. D. Bella, Synthesis, Characterization, Optical Absorption/ Fluorescence Spectroscopy, and Second-Order Nonlinear Optical Properties of Aggregate Molecular Architectures of Unsymmetrical Schiff-Base Zinc(Ii) Complexes Dalton Trans., Vol. 43, 2014, pp. 2168-2175.
https://doi.org/10.1039/C3DT53072H.
[14] I. P. Oliveri, S. Failla, G. Malandrino, S. D. Bella, New Molecular Architectures by Aggregation of Tailored Zinc(Ii) Schiff-Base Complexes, New. J. Chem., Vol. 35, 2011, pp. 2826-2831. https://doi.org/10.1039/C1NJ20618D.
[15] I. P. Oliveri, S. Failla, G. Malandrino, S. D. Bella, Controlling the Molecular Self-Assembly into Nanofibers of Amphiphilic Zinc(II) Salophen Complexes, J. Phys. Chem. C, Vol. 117, 2013, pp. 15335-15341.
https://doi.org/10.1021/jp4038182.
[16] I. P. Oliveri, G. Maccarrone, S. D. Bella, A Lewis Basicity Scale in Dichloromethane for Amines and Common Nonprotogenic Solvents Using a Zinc(II) Schiff-Base Complex as Reference Lewis Acid, J. Org. Chem., Vol. 76, 2011, pp. 8879-8884. https://doi.org/-10.1021/jo2016218.
[17] I. P. Oliveri, G. Malandrino, S. D. Bella, Self-Assembled Nanostructures of Amphiphilic Zinc(Ii) Salophen Complexes: Role of the Solvent on Their Structure and Morphology, Dalton Trans., Vol. 43, 2014, pp. 10208-10214.
https://doi.org/10.1039/C4DT00973H.
[18] I. P. Oliveri, G. Malandrino, S. D. Bella, Supramolecular Aggregation/Deaggregation in Amphiphilic Dipolar Schiff-Base Zinc(II) Complexes, Inorg. Chem., Vol. 53, 2014, pp. 9771-9777. https://doi.org/-10.1021/ic5013632.
[19] P. Wang, Z. Hong, Z. Xie, S. Tong, O. Wong, C.-S. Lee, N. Wong, L. Hung, S. Lee, A Bis-Salicylaldiminato Schiff Base and Its Zinc Complex as New Highly Fluorescent Red Dopants for High Performance Organic Electroluminescence Devices, Chem. Commun., 2003, pp.1664-1665.
https://doi.org/10.1039/B303591C.
[20] T. Yu, W. Su, W. Li, Z. Hong, R. Hua, B. Li, A Schiff Base Zinc Complex and its Electroluminescent Properties, Thin Solid Films, Vol. 515, 2007, 4080.
https://doi.org/10.1016/j.tsf.2006.11.001.
[21] L. X. Dien, K. Yamashita, M. S. Asano, K. Sugiura, Syntheses of A Pyrene-Based Π-Expanded Ligand and the Corresponding Platinum(II) Complex, Bis[2-[(Octylimino)Methyl]-1-Pyrenolato-N,O] Platinum(II), Inorg. Chim. Acta, Vol. 432, 2015, pp. 103-108.
https://doi.org/10.1016/j.ica.2015.03.038.
[22] T. Ohno, S. Kato, A. Takeuchi, S. Yamada, Excited States of N-Salicylidenealkylamines Chelating to Zinc(II), Bull. Chem. Soc. Jpn., Vol 50, 1977, pp. 6-9.
https://doi.org/-10.1246/bcsj.50.6.
[23] G. E Batley, D. P Graddon, Studies in the Stereochemistry Of Zinc(II). V. Zinc Complexes With N-Alkylsalicylaldimines, Australian Journal of Chemistry, Vol. 20, 1967, pp. 877-883. https://doi.org/-10.1071/CH9670877.
[24] H. N. Hou, Acta Cryst. Bis[2-(cyclohexyliminomethyl)phenolato]zinc(II), E61, 2005, pp. m1197-m1198.
https://doi.org/10.1107/S1600536805015990.
[25] Z. L. You, Bis[2-(cyclohexyliminomethyl)-4-nitrophenolato]zinc(II), Acta Cryst., E61, 2005, pp. m2495-m2496.
https://doi.org/10.1107/S1600536805035531.
[26] Z. X. Li, X. L. Zhang, Bis[4-chloro-2-(cyclohexyliminomethyl)phenolato]zinc(II), Acta Cryst., E61, 2005, pp. m1755-m1756. https://doi.org/10.1107/-S1600536805025250.
[27] P. Demerseman, J. Einhorn, R. Royer, J. F. Gourvest, Synthèse D'analogues Furanniques du Benzo[a]pyrene, J. Heterocycl. Chem., Vol. 22, 1985, pp. 39-43.
https://doi.org/10.1002/jhet.5570220110.
[28] L. X. Dien, K. Yamashita, K. Sugiura, Metal Complexes of π-expanded Ligands (2): Synthesis and Characterizations of bis[2-[(octylimino)methyl]-1-pyrenolato-N,O] palladium(II) and the Stabilized Vacant dx2 - y2 orbital, Polyhedron, Vol. 102, 2015, pp. 69-74. https://doi.org/10.1016/-j.poly.2015.07.043.
[29] L. X. Dien, N. X. Truong, N. D. Quan, K. Yamashita, K. Sugiura, Synthesizing and Studying the Structure of Ni(II) Complexes Containing 2-alkyliminomethyl Pyrene Ligands, VNU Journal of Science, Vol. 34, No. 4, 2018, pp. 16-20.
https://doi.org/-10.25073/2588-1140/vnunst.4809.
[30] L. X. Dien, N. K. Nga, N. X. Truong, K. Yamashita, K. Sugiura, Metal Complexes of π-Expanded Ligands (4): Synthesis and Characterizations of Copper(II) Complexes with a Schiff Base Ligand Derived from Pyrene, VNU Journal of Science, Vol. 35, No. 2, 2019, pp. 98-105.
https://doi.org/10.25073/25881140/-vnunst.4898.