Synthesis and Characterization of a New Optical Cd(II) Mixed-Ligand Complex as a Precursor for the Fabrication of Organic Light-Emitting Diodes

Document Type : Research Article

Authors

Department of Chemistry, Payame Noor University (PNU), Tehran, Iran

Abstract

A new optical mixed-ligand complex of cadmium(II), [(C15H9O2)(OMe)2(Me2Sn)4O2] (1), was prepared from the reaction of cadmium nitrate with anthracene-9-carboxylic acid and bipyridine ligands by the branched tube method and the prepared compound was fully characterized  by IR, UV spectroscopies and elemental analysis. The solid state structure of 1 was also investigated via single crystal XRD. The results showed that compound 1 is a mononuclear complex crystallized in triclinic system with space group of. The asymmetric unit of 1 is comprised of one cadmium ion, one anthracene-9-carboxylate anion, two bipyridine ligands and one nitrate anion. The thermal stability of the prepared complex was investigated by thermal gravimetric method (TGA). The prepared complex was used as light emission layers in two different concentrations in the fabrication of organic light-emitting diodes. Examining the results showed that the concentration of the complex has a significant effect on the electrical properties of the prepared diodes.

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References

[1] Darzinezhad K., Amini M. M., Janghouri M., Mohajerani E., Fathollahi M. R., Jamshidi Z., Janiak C.,  Introducing Bluish-Green Light-Emitting Diodes (OLEDs) and Tuning Their Color Intensity by Uranium Complexes: Synthesis, Characterization, and Photoluminescence Studies of 8-Hydroxyquinoline Complexes of Uranium, Inorg. Chem., 59: 17028- 17037 (2020).
[2] Darzinezhad K., Amini M. M., Mohajerani E., Fathollahi M. R., Janghouri M., Notash B., Rostami A., Architecture of New Rare Earth Metal Complexes as Precursors for the Fabrication of a New Class of OLEDs with Blue Shift Fluorescence, Z. Anorg. Allg. Chem., 647: 456-462 (2021). 
[3] Kagatikar S., Sunil D., Schiff  Bases and Their Complexes in Organic Light Emitting Diode Application, J. Electron. Mater., 50: 6708–6723 (2021).
 [4] Miao Y., Tao P., Wang K., Li H., Zhao B., Gao L., Wang H., Xu B., Zhao Q., Highly Efficient Red and White Organic Light-Emitting Diodes with External Quantum Efficiency beyond 20% by Employing Pyridylimidazole-Based Metallophosphors, Appl. Mater. Interfaces., 9: 37873–37882 (2017).
 [5] Tang M.C., Chan M. Y., Yam V. W. W., Molecular Design of Luminescent Gold(III) Emitters as Thermally Evaporable and Solution-Processable Organic Light-Emitting Device (OLED) Materials, Chem. Rev., 121: 7249–7279 (2021).
[6] Panigati M., Mauro M., D’Alfonso G., Luminescent Dinuclear Rhenium(I) Complexes Containing Bridging 1,2-Diazine Ligands: Photophysical Properties and Application, Coord. Chem. Rev., 256: 1621-1643 (2021).
[7] Lee J. H., Chen C. H., Lee P. H., Lin H. Y., Leung M. k., Chiu T. L., Lin C. F., Blue Organic Light-Emitting Diodes: Current Status, Challenges, and Future Outlook, J. Mater. Chem. C., 7: 5874–5888 (2019).
[8] Kim S., Lee J. I., Yang J., Shin I. S., Earmme T., Kang M. S., A Guide for Realizing Efficient Polymer Light-Emitting Electrochemical Cells in a Single Active Layer Device Structure, Chem. Electro. Chem., 7: 260–265 (2020).
 [9] Meier S. B., Tordera D., Pertegas A., Roldan-Carmona C., Orti E., Bolink H. J., Light-Emitting Electrochemical Cells: Recent Progress and Future Prospects, Mater. Today., 17: 217–223 (2014).
[10] Matsuki K., Pu J., Takenobu T., Recent Progress on Light-Emitting Electrochemical Cells with Nonpolymeric Materials, Adv. Funct. Mater., 30: 1908641-1908649 (2020).
 [11] Kwon D.K., Myoung J. M., Ion Gel-Based Flexible Electrochemiluminescence Full-Color Display with Improved Sky-Blue Emission Using a Mixed-Metal Chelate System, Chem. Eng. J., 379: (2020)122347.
[12]  Mohammadnezhad G., Nasimpour F.,Amini M. M.,Najafi E.,Winfrie H.G.,  Sabzaliane M. R., Synthesis, Spectroscopic and X-Ray Structural Characterization of Two Novel Mixed-Ligand Lead(II) Complexes, J. Mol. Struct., 1175: 471-480 (2019).
 [13]  Amani V., Safari N., Khavasi H. R., Mirzaei P., Iron (III) Mixed-Ligand Complexes: Synthesis, Characterization and Crystal Structure Determination of Iron(III) Complexes Containing 4,4′-Dimethyl-2,2′-Bipyridine, Dimethyl Sulfoxide and Chloride, [Fe(Dmbipy)Cl4][dmbipyh] and [Fe(Dmbipy)Cl3(DMSO)], Polyhedron., 26: 4908–4914 (2007).
[14]   Devi R.,  Boddula R.,  Singh K., Kumar S., Vaidyanathan S., New Europium Complexes and Their Use in Red Light-Emitting Diodes and Vapoluminescent Sensors, 22: 137-151 (2021).
 [15]Yin Z., Zhou Y. L., Zeng M. H., Kurmoo M., The Concept of Mixed Organic Ligands in Metal–Organic Frameworks: Design, Tuning and Functions, Dalt. Trans., 44: 5258–5275 (2015).
[16] Du M., Li C. P., Liu C. S., Fang S. M., Design and Construction of Coordination Polymers with Mixed-Ligand Synthetic Strategy, Coord. Chem. Rev., 257: 1282–1305 (2013).
 [17] lmi R., Haque A., Busaidi I. J. A.,  Rasbi N. K. A., Khan M. S., Synthesis and Photophysical Properties of Hetero Trinuclear Complexes of tris β-Diketonate Europium with Organoplatinum Chromophore, Dyes. Pigm., 162: 59-66 (2019).
 [18] Abebe A., Kendie M., Tigineh G. T., Mono-and Binuclear Cobalt(II) Mixed Ligand Complexes of 2,2’-Bipyridine and Ethylenediamine: Synthesis, Characterization and Biological Application, Biointerface. Res. Appl. Chem., 12: 1962–1973 (2022).
[19]  Casado F.J.M., Canadillas-Delgado L., Cucinotta F., Guerrero-Martínez A., Riesco M.R., Marchese L., Cheda J.A.R., Luminescent Lead (II) Complexes: New Three-Dimensional Mixed Ligand MOFs, Cryst. Eng. Comm., 14: 2660–2668 (2012).
 [20] Chen L., Yan C., Pan M., Fan Y. Z., Zhang L. Y., S.-Y. Yin, Hou Y. J., Wu K., Jiang J. J., Su C. Y., Semidirected Versus Holodirected Coordination and Single-Component white Light Luminescence in Pb (II) Complexes, New. J. Chem., 39: 5287–5292 (2015).
[21] Hamada Y., Sano T., Shibata K., Kuroki K., Influence of the Emission Site on the Running Durability of Organic Electroluminescent Devices, Jpn. J. Appl. Phys., 34: L824-828 (1995).
[22] Zeng W. F., Chen Y.S., Chiang M.Y., Chern S.S., Cheng C.P., Preparation and Structures of Complexes of Titanium (IV) and 8-Hydroxyquinoline: TiQ2(Opri)2 and [TiQ2(μ-O)]4· 6H2O, Polyhedron., 21: 1081-1087 (2002).
[23] Qin Y., Pagba C., Piotrowiak P., Jakle F., Luminescent Organoboron Quinolate Polymers, J. Am .Chem. Soc.,126: 7015–7018 (2004).
[24] Brinkmann M., Fite B., Pratontep S., Chaumont C., Structure and Spectroscopic Properties of the Crystalline Structures Containing Meridional and Facial Isomers of Tris(8-hydroxyquinoline) Gallium(III), Chem. Mater., 16: 4627–4633 (2004).
[25] Burrows P. E., Sapochak L. S., McCarty D. M., Forrest S. R., Thompson M. E., Metal Ion Dependent Luminescence Effects in Metal Tris-Quinolate Organic Heterojunction Light Emitting Devices, Appl. Phys. Lett., 64: 2718- 2720 (1994).
[26]  Burrows P. E., Shen Z., Bulovic V., McCarty D. M., Forrest S. R., Cronin J. A., Thompson M. E., Relationship Between Electroluminescence and Current Transport in Organic Heterojunction Light-Emitting Devices, J. Appl. Phys., 79: 7991-7999 (1996).
[27] Sapochak L. S., Benincasa F. E., Schofield R. S., Baker J. L., Riccio K. K., Fogarty D., Kohlmann H., Ferris K. F., Burrows P. E., Electroluminescent Zinc(II) Bis(8-Hydroxyquinoline): Structural Effects on Electronic States and Device Performance, J. Am. Chem. Soc.,124: 6119-6125 (2002).
[28] Shavaleev N. M., Adams H., Best J., Edge R., Navaratnam S., Weinstein J. A., Deep-Red Luminescence and Efficient Singlet Oxygen Generation by Cyclometalated Platinum(II) Complexes with 8-Hydroxyquinolines and Quinoline-8-thiol, Inorg. Chem., 45: 9410-9415 (2006).
[29] Kolb A., Bissinger P., Schmidbaur H., Synthesis of Aryl Bis[(Triorganophosphine) Gold(I)]Oxonium Tetrafluoroborates [RO(AuPR'3)2]+BF4-. CRYSTAL Structure of (8-Quinolinyl)Bis[(Triphenylphosphine)Gold(I)]Oxonium Tetrafluoroborate, Inorg. Chem., 32: 5132-5135 (1993).
[30]  Helfrich W., Schneider W.G., Recombination Radiation in Anthracene Crystals, Phys. Rev. Lett., 14: 229-234 (1965).
[31] Helfrich W., Schneider W.G., Transients of Volume-Controlled Current and of Recombination Radiation in Anthracene, J. Chem. Phys., 44: 2902-2906 (1966).
 [32] Momiji I., Yoza C., Matsui K., Fluorescence Spectra of 9-Anthracenecarboxylic Acid in Heterogeneous Environments, J. Phys. Chem. B., 104: 1552-1555 (2000).
[33] Suzuki S., Fujii T., Yoshiike N., Komatsu S., Iida T., Absorption and Fluorescence Spectra of Anthracenecarboxylic Acids and 9-Anthroic Acid and Formation of Excimer, Bull. Chem. Soc. Jpn., 51: 2460-2466 (1978).
[34] Ghoneim N., Scherrer D., Suppan P.J., Dual Luminescence, Structure and Excimers of 9-Anthracene Carboxylic Acid,  Luminescence., 55: 271-275 (1993).
[35] Froemmel J., Wolff T., Influence of Ionene Polyelectrolytes on Rheology and Photorheology of Aqueous Micellar Cetyltrimethylammonium Bromide Containing 9-Anthracene Carboxylic Acid, J. Colloid.  Interface Sci., 201: 86-92 (1998).
[36] Cohen M. D., Ludmer Z., Yakhot V., The Fluorescence Properties of Crystalline Anthracenes and Their Dependence on the Crystal Structures, Phys. Status. Solidi.B., 67: 51-61 (1975).
[37] Chena C.L., Linb M.H., Hongb J.L., Hydrogen-bond Interactions and Photoluminescence Properties of the Miscible Blends of 9-Anthracenecarboxylic Acid and Polycyanate Crosslinked Resin, Synth. Met., 148: 61-64 (2005).
[38] Najafi E., Amini M. M., Vessally E., Gholami M., Ng S. W., Tuning Of Optical Properties Of A New Class Of Tin Coordination Compounds By Changing In The Π-Conjugation Length Of Ancillary Ligands, Inorg. Chim.Acta., 463: 61–69 (2017).
[39] Amini M. M., Najafi E., Saeidian H., Mohammadi E., Shahabi S. M., Ng S. W., Effect of Pseudohalogen Groups on the Optical Properties and the Structures of Diorganotin Coordination Compounds Based on the Flexible Ligand 1,2,3,4-Tetra-(4-Pyridyl)-Butane, Appl. Organomet. Chem., 31: e3884-3888 (2017).
[40] Najafi E., Amini M. M., Taherbateni S.,  Memarian H., Ng S. W., Synthesis, Characterization, and Photophysical Properties of a New Class of Diorganotin(IV)Cupferronato Complexes with Pyridyl-Based Ancillary Ligands With Different Conjugated π-System, Monatsh. Chem., 149: 1379–1388 (2018).
[41] Najafi E., Amini M. M.,  Yousefi P., Ng S. W., Metal-Ion Type Effect on the Crystal Structure and Optical Properties of 2,2′-bipyridine Complexes of Pb(II) and Cd(II), J. Inorg. Organomet. Polym. Mater., 28:1801–1809 (2018).
[42] Tang C., VanSlyke S., Organic Electroluminescent Diodes, Appl. Phys. Lett., 51: 913-917 (1987).
[43]  Knox J. E., Halls M. D., Hratchian H. P.,  Schlegel H. B., Chemical Failure Modes of AlQ3-Based OLEDs: AlQ3 Hydrolysis,  Phys. Chem. Chem. Phys., 8: 1371-1377 (2006).
[44] Brinkmann M., Gadret G., Muccini M., Taliani C., Masciocchi N., Sironi A., Correlation Between Molecular Packing and Optical Properties in Different Crystalline Polymorphs and Amorphous Thin Films of  Mer-Tris(8-Hydroxyquinoline)Aluminum(III), J. Am. Chem. Soc.,122: 5147-5157 (2000).
[45] Perrin D. D., Armarego W. L. F., Purification of Laboratory Chemicals. 2nd Edition, Pergamon Press, New York, (1980).
[46] Sheldrick G. M., SHELXL2017/1, Program for Crystal Structure Solution & Refinement, University of Göttingen, Germany, (2017).
[47]  Liu C.S., Wang J. J., Chang Z., Yan L. F., Cadmium(II) Complexes with a Bulky Anthracene-Based Carboxylate Ligand: Syntheses, Crystal Structures, and Luminescent Properties, Z. Anorg. Allg. Chem., 636: 1115-1123 (2010).
[48] Najafi E., Kheirkhahi M., Amini M.M., Ng S.W., Preparation of SnO2 Nanoparticles from a New Tin(IV) Complex: Spectroscopic and Photoluminescence Studies, J. Inorg. Organomet.Polym., 23: 1015-1022 (2013).
 [49] Shahroosvand H., Nasouti F.  ,Mohajerani E.,Khabbazi A., Red–Yellow Electroluminescence, Yellow–Green Photoluminescence of Novel N, O Donor Ligands–Chelated Zirconium (IV) Complexes, J. Lumin., 135: 339-344 (2013).
[50] Liu C.S., Wang J.J., Chang Z., Yan L.F., Bu X.H., Cadmium(ii) Coordination Polymers Based on a Bulky Anthracene-Based Dicarboxylate Ligand: Crystal Structures and Luminescent Properties, Cryst. Eng.Comm., 12: 1833-1841 (2010).
[51] Tseng T.W., Yang M.L., Luo T.T., A Key Route to Designing Huge Eight-Fold Interpenetrated Coordination Networks with Ths-Type Topology: Synthesis, Structures, and Topological Characteristics, J. Solid. State. Chem., 221: 345-350 (2015).
[52] Mehrani A., Morsali A., Synthesis and Crystal Structures of Mercury(II) and Cadmium(II) Coordination Compounds using 4′-(4-Pyridyl)-2,2′:6′,2′-Terpyridine Ligand and their Thermolysis to Nanometal Oxides, J. Mol. Struct., 1074: 596-601 (2014).
[53]  Wang J.J., Liu C.S., Hu T.L., Chang Z., Li C.Y., Yan L.F., Chen P.Q., Bu X.H., Wu Q., Zhao L.J., Wang Z., Zhang X. Z., Zinc(II) Coordination Architectures with Two Bulky Anthracene-Based Carboxylic Ligands: Crystal Structures and Luminescent Properties, Cryst. Eng.Comm., 10: 681-692 (2008).
[54] Janghouri M., Mohajerani E., Mostafa M.M., Najafi E., Hosseini H., Yellow–Orange Electroluminescence of  Novel Tin Complexes, J. Electron. Mater., 42: 2915–2925 (2013).
[55] Galanin M.D., Luminescence of Molecules and Crystals. Cambridge International Science, Cambridge, 69 (1996).
Nashrieh Shimi va Mohandesi Shimi Iran
Volume 42, Issue 4 - Serial Number 110
December 2023
Pages 105-119

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