Bazı Organik Elektrolüminesans 2-[3-(Metil/Etil/p-Metilbenzil)-5-okso-1H-1,2,4-triazol-4(5H)-yl]-izoindolin-1,3-dionlar'ın Yoğunluk Fonksiyon Teorisi ile Elektronik Özelliklerinin Belirlenmesi

Year 2021, Volume: 8 Issue: 2, 185 - 197, 31.12.2021

Murat Beytur , Zeynep Şilan Turhan , Haydar Yüksek

https://doi.org/10.48138/cjo.1032713

Abstract

Son zamanlarda bilim adamlarının ilgisini çeken 4,5-dihidro-1H-1,2,4-triazol-5-on türevlerinin potansiyel organik elektrominesans özellikleri tartışılmaktadır. Bu heterosiklik organik bileşiklerin elektronik özellikleri hesaplama yöntemleriyle incelenmiştir. Hesaplama işlemleri Windows işletim sistemlerinde çalışan yüksek performanslı sunucu sistemleri ile yapılmıştır. . 2-[3-(metil/etil/p-metilbenzil)-5-okso-1H-1,2,4-triazol-4(5H)-il]-izoindolin-1,3-dionların geometrileri GaussView 5.0 bilgisayar programı kullanılarak çizilmiştir. Teorik hesaplamalar Gaussian09W programı kullanılarak yapılmıştır. Daha sonra teorik hesaplamalarla optimize edilen moleküllerin HOMO-LUMO şekilleri elde edilmiştir. Her molekülün HOMO-LUMO enerji farkı (ΔE) eV cinsinden hesaplanmıştır. Sonuçlar ilgili literatürden elde edilen değerlerle karşılaştırılmıştır. Bu çalışmada kullanılan DFT (Yoğunluk Fonksiyonu Teorisi) yönteminin B3LYP 6-311G++(d,p) ve CAMB3LYP 6-311G++(d,p) temel set hesaplamalarından elde edilen teorik ve simülasyon sonuçlarına göre; HOMO-LUMO enerji farklılıkları incelendiğinde, çalışılan ilgili moleküller arasından optoelektronik özelliklere sahip olabilecek potansiyel moleküllerin olduğu belirlenmiştir. Bu yüzden, çalışmanın optoelektronik malzemelerin elde edilmesi açısından sentetik organik kimya prosedürlerine ışık tutması beklenmektedir. Organik elektronik cihazlar, optoelektronik özellikleri nedeniyle oldukça dikkat çekicidir. Bu cihazlar üç ana başlık altında incelenebilir. Bunlar organik ışık yayan diyot (OLED), organik ince film transistörler (OTFT) ve organik güneş pilleridir. Bu cihazlar genellikle birbiri üzerine yerleştirilmiş anot-organik malzeme-katot tabakaları şeklinde yapılandırılmıştır.

Keywords

1.2.4-Triazol-5-on, Organik Işık Yayan Diyot, Elektrolüminesan Moleküller

Determination of The Electronic Properties of Some Organic Electroluminescent 2-[3-(Methyl/Ethyl/p-Methylbenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl]-isoindoline-1,3-diones with Density Function Theory

Abstract

The potential organic electroluminescent properties of 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives that have recently attracted much of the scientists' interest is discussed. The electronic features of these heterocyclic organic compounds are examined with computational methods. The calculation operations were conducted with the high-performance server systems running on Windows operating systems. The geometries of the studied molecules were plotted using the GaussView 5.0 computer program. Theoretical calculations were conducted using the Gaussian09W program. Then, the HOMO-LUMO shapes of the molecules that were optimized with theoretical calculations were obtained. The HOMO-LUMO energy difference (ΔE) of each molecule was calculated in terms of eV. The results were compared with the values obtained from relevant literature. According to the theoretical and simulation results obtained from the B3LYP 6-311G++(d,p) and CAMB3LYP 6-311G++(d,p) basic set calculations of the DFT (Density Functional Theory) method used in this study; when the HOMO-LUMO energy differences were examined, it was determined that from among the studied candidate molecules, there were potential molecules that have/could have optoelectronic features. Therefore, it is expected that the study will shed light on synthetic organic chemistry procedures in terms obtaining optoelectronic materials. Organic electronic devices are quite remarkable due to their optoelectronic features. These devices can be examined under three main headings. These are organic light emitting diode (OLED), organic thin-film transistors (OTFT) and organic solar cells. These devices are usually structured in the form of anode-organic material-cathode layers placed on top of each other.

Keywords

1.2.4-Triazol-5-one, Organic Light Emitting Diode, Electroluminescent Molecules, Density Functional Theory.

References

• Arivazhagan, M., & Subhasini, V. P. (2012). Quantum chemical studies on structure of 2-amino-5-nitropyrimidine. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 91, 402–410. https://doi.org/10.1016/j.saa.2012.02.018
• Arun, V., Mathew, S., Robinson, P. P., Jose, M., Nampoori, V. P. N., & Yusuff, K. K. M. (2010). The tautomerism, solvatochromism and non-linear optical properties of fluorescent 3-hydroxyquinoxaline-2-carboxalidine-4-aminoantipyrine. Dyes and Pigments, 87(2), 149–157. https://doi.org/https://doi.org/10.1016/j.dyepig.2010.03.012
• Bahçeci, Yıldırım, N., Gürsoy-Kol, Manap, S., Beytur, M., & Yüksek, H. (2016). Synthesis, characterization and antioxidant properties of new 3-alkyl (Aryl)-4-(3-hydroxy-4-methoxy-benzylidenamino)-4,5-dihydro-1h-1,2,4-triazol-5-ones. Rasayan Journal of Chemistry, 9(3), 494–501.
• Becke, A. D. (1996). Density-functional thermochemistry. IV. A new dynamical correlation functional and implications for exact-exchange mixing. Journal of Chemical Physics, 104(3), 1040–1046. https://doi.org/10.1063/1.470829
• Beytur, M. (2020). Fabrication of Platinum Nanoparticle/Boron Nitride Quantum Dots/6-Methyl-2-(3-hydroxy-4-methoxybenzylİdenamİno)-benzothİazole (ILS) Nanocomposite For Electrocatalytic Oxidation of Methanol. Journal of the Chilean Chemical Society, 65(3), 4929–4933. https://doi.org/10.4067/s0717-97072020000204929
• Beytur, M., & Avinca, I. (2021). Molecular, Electronic, Nonlinear Optical and Spectroscopic Analysis of Heterocyclic 3-Substituted-4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones: Experiment and DFT Calculations. Heterocyclic Communications, 27(1), 1–16. https://doi.org/doi:10.1515/hc-2020-0118
• Beytur, M., Turhan Irak, Z., Manap, S., & Yüksek, H. (2019). Synthesis, characterization and theoretical determination of corrosion inhibitor activities of some new 4,5-dihydro-1H-1,2,4-Triazol-5-one derivatives. Heliyon, 5(6). https://doi.org/10.1016/j.heliyon.2019.e01809
• Boy, S., Türkan, F., Beytur, M., Aras, A., Akyıldırım, O., Karaman, H. S., & Yüksek, H. (2021). Synthesis, design, and assessment of novel morpholine-derived Mannich bases as multifunctional agents for the potential enzyme inhibitory properties including docking study. Bioorganic Chemistry, 107, 104524. https://doi.org/https://doi.org/10.1016/j.bioorg.2020.104524
• Çiftçi, E., Beytur, M., Calapoğlu, M., Gürsoy-Kol, Ö., Alkan, M., Toğay, A., Manap, S., & Yüksek, H. (2018). Synthesis, Characterization, Antioxidant and Antimicrobial Activities and DNA Damage of Some Novel 2-[3-alkyl (aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-phenoxyacetic acids in Human Lymphocytes. Research Journal of Pharmaceutical, Biological and Chemical Sciences, 9, 1760–1771.
• Danel, A., Chacaga, Ł., Uchacz, T., Pokladko-Kowar, M., Gondek, E., Karasiński, P., & Sahraoui, B. (2015). Solution processable double layer organic light emitting diodes (OLEDs) based on 6- N , N -arylsubstituted-1 H -pyrazolo[3,4- b ]quinolines . Advanced Device Materials, 1(1), 17–22. https://doi.org/10.1179/2055031614y.0000000004 Dennington, R., Keith, T., & Millam, J. (2009). GaussView, Version 5, (Version 5).
• Foresman, J. B., & Frisch, A. (1996). Exploring Chemistry with Electronic Structure Methods Gaussian (2nd editio).
• Forrest, S. R. (2004). The path to ubiquitous and low-cost organic electronic appliances on plastic. Nature, 428(6986), 911–918. https://doi.org/10.1038/nature02498
• Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., & Sonnenbe, D. J. (2009). Gaussian 09 (Revision E).
• Gallardo, H., Conte, G., Bortoluzzi, A. J., Bechtold, I. H., Pereira, A., Quirino, W. G., Legnani, C., & Cremona, M. (2011). Synthesis, structural characterization, and photo and electroluminescence of a novel terbium(III) complex: {Tris(acetylacetonate) [1,2,5]thiadiazolo[3,4-f][1,10]phenanthroline}terbium(III). Inorganica Chimica Acta, 365(1), 152–158. https://doi.org/https://doi.org/10.1016/j.ica.2010.09.003
• Gökce, H., & Bahçeli, S. (2011). A study on quantum chemical calculations of 3-, 4-nitrobenzaldehyde oximes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 79(5), 1783–1793. https://doi.org/https://doi.org/10.1016/j.saa.2011.05.057
• Guezguez, I., Ayadi, A., Ordon, K., Iliopoulos, K., Branzea, D. G., Migalska-Zalas, A., Makowska-Janusik, M., El-Ghayoury, A., & Sahraoui, B. (2014). Zinc Induced a Dramatic Enhancement of the Nonlinear Optical Properties of an Azo-Based Iminopyridine Ligand. The Journal of Physical Chemistry C, 118(14), 7545–7553. https://doi.org/10.1021/jp412204f
• Gupta, K. C., & Sutar, A. (2008). Catalytic Activities of Schiff Base Transition Metal Complexes. Coordination Chemistry Reviews, 252, 1420–1450. https://doi.org/10.1016/j.ccr.2007.09.005
• Ikizler, A., & Un, R. (1996). Reactions of ester ethoxycarbonylhydrazones with some amine type compounds. Revue Roumaine de Chimie, 41(7), 585–590.
• Jesudason, E. P., Sridhar, S. K., Malar, E. J. P., Shanmugapandiyan, P., Inayathullah, M., Arul, V., Selvaraj, D., & Jayakumar, R. (2009). Synthesis, pharmacological screening, quantum chemical and in vitro permeability studies of N-Mannich bases of benzimidazoles through bovine cornea. European Journal of Medicinal Chemistry, 44(5), 2307–2312. https://doi.org/10.1016/j.ejmech.2008.03.043
• Kardas, F., Manap, S., Gürsoy-Kol, Ö., Beytur, M., & Yüksek, H. (2016). Synthesis and antioxidant properties of some 3-Alkyl(Aryl)-4-[3-ethoxy-2-(4- toluenesulfonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones. Der Pharma Chemica, 8(18), 274–281.
• Karelson, M., Lobanov, V. S., & Katritzky, A. R. (1996). Quantum-Chemical Descriptors in QSAR/QSPR Studies. Chemical Reviews, 96(3), 1027–1044. https://doi.org/10.1021/cr950202r
• Kiyooka, S., Kaneno, D., & Fujiyama, R. (2013). Parr’s index to describe both electrophilicity and nucleophilicity. Tetrahedron Letters, 54, 339–342. https://doi.org/10.1016/j.tetlet.2012.11.039
• Koç, E., Yüksek, H., Beytur, M., Akyildirim, O., Akçay, M., Beytur, C., Üniversitesi, K., Fakültesi, M. M., & Bölümü, B. (2020). Araştırma Makalesi / Research Article Heterosiklik 4 , 5-dihidro-1 H -1 , 2 , 4-triazol-5- on Türevinin Antioksidan Özelliğinin Erkek Ratlarda ( Wistar albino ) İn vivo Olarak Belirlenmesi In vivo Determination of Antioxidant Properties of Heterocyclic 4 , 5- dihydro-1 H -1 , 2 , 4-triazole-5-one Derivative in Male Rats ( Wistar albino ). 9(2), 542–548.
• Kohn, W., & Sham, L. J. (1965). Self-Consistent Equations Including Exchange and Correlation Effects. Phys. Rev., 140(4A), A1133--A1138. https://doi.org/10.1103/PhysRev.140.A1133 Koopmans, T. (1934). Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms. Physica, 1(1), 104–113. https://doi.org/https://doi.org/10.1016/S0031-8914(34)90011-2
• Kotan, G., Gökce, H., Akyıldırım, O., Yüksek, H., Beytur, M., Manap, S., & Medetalibeyoğlu, H. (2020). Synthesis, Spectroscopic and Computational Analysis of 2-[(2-Sulfanyl-1H-benzo[d]imidazol-5-yl)iminomethyl]phenyl Naphthalene-2-sulfonate. Russian Journal of Organic Chemistry, 56(11), 1982–1994. https://doi.org/10.1134/S1070428020110135 Li, X., Deng, S., & Fu, H. (2011). Three pyrazine derivatives as corrosion inhibitors for steel in 1.0M H2SO4 solution. Corrosion Science, 53, 3241–3247. https://doi.org/10.1016/j.corsci.2011.05.068
• Malenfant, P. R. L., Dimitrakopoulos, C. D., Gelorme, J. D., Kosbar, L. L., Graham, T. O., Curioni, A., & Andreoni, W. (2002). N-type organic thin-film transistor with high field-effect mobility based on a N,N′-dialkyl-3,4,9,10-perylene tetracarboxylic diimide derivative. Applied Physics Letters, 80(14), 2517–2519. https://doi.org/10.1063/1.1467706
• Masoud, M. S., Ali, A. E., Shaker, M. A., & Elasala, G. S. (2012). Synthesis, computational, spectroscopic, thermal and antimicrobial activity studies on some metal-urate complexes. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 90, 93–108. https://doi.org/10.1016/j.saa.2012.01.028
• Murthy, Y. L. N., Karthikeyan, N., Boddeti, G., Diwakar, B. S., & Singh, E. R. (2011). Design, synthesis and in vitro antibacterial activities of methyl-4-((substituted phenyl) [6H-indolo (2,3-b)quinoxalin-6-yl]methyl-amino) benzoate derivatives. Chinese Chemical Letters, 22(5), 567–570. https://doi.org/10.1016/j.cclet.2010.10.055
• Özbek, F. E., Sertçelik, M., Yüksek, M., Uğurlu, G., Tonbul, A. M., Necefoğlu, H., & Hökelek, T. (2019). Synthesis and Crystallographic, Absorption and Emission Studies of 4-Pyridine Carboxamide of Zn(II) 4-Chlorophenylacetate. Journal of Fluorescence, 29(5), 1265–1275. https://doi.org/10.1007/s10895-019-02440-x
• Öztürkkan, F. E., Sertçelik, M., Yüksek, M., Necefoğlu, H., & Hökelek, T. (2021). Hirshfeld surface analysis, interaction energy calculations of metal (II)4-cyanobenzoate with nicotinamide/N,N’-diethylnicotinamide complexes. Journal of the Turkish Chemical Society, Section A: Chemistry, 8(1), 125–136. https://doi.org/10.18596/jotcsa.824551
• Öztürkkan Özbek, F. E., Sertçelik, M., Yüksek, M., Elmalı, A., & Şahin, E. (2020). The superiority of the classical synthesis compared to the hydrothermal synthesis upon the structural, optical absorption and fluorescent properties of new Cd(II) 3-fluorobenzoate complexes with Pyridine-3-carboxamide/Pyridine-3-carboxylate. Inorganica Chimica Acta, 509, 119694. https://doi.org/https://doi.org/10.1016/j.ica.2020.119694
• Pearson, R. G. (1988). Absolute electronegativity and hardness: application to inorganic chemistry. Inorganic Chemistry, 27(4), 734–740. https://doi.org/10.1021/ic00277a030
• Sabbatini, N., Guardigli, M., & Lehn, J.-M. (1993). Luminescent lanthanide complexes as photochemical supramolecular devices. Coordination Chemistry Reviews, 123(1), 201–228. https://doi.org/https://doi.org/10.1016/0010-8545(93)85056-A
• Sastri, V. S., & Perumareddi, J. R. (1997). Molecular Orbital Theoretical Studies of Some Organic Corrosion Inhibitors. Corrosion (Houston), 53(8), 617–622. https://doi.org/10.5006/1.3290294
• Sertçelik, M., Akbaba, G. B., & Öztürkkan, F. E. (2021). Kobalt ( II ) ve Çinko ( II ) 4- Florobenzoatın 3 -Hidroksipiridin Komplekslerinin Sentezi , Spektroskopik ve Sitotoksik Özellikleri. Ii, 0–2.
• Sertçelik, M., Öztürkkan Özbek, F. E., Taslimi, P., Necefoglu, H., & Hökelek, T. (2021). Supramolecular complexes of Ni (II) and Co (II) 4-aminobenzoate with 3-cyanopyridine: Synthesis, spectroscopic characterization, crystal structure, and enzyme inhibitory properties. Applied Organometallic Chemistry, 35(5), 1–10. https://doi.org/10.1002/aoc.6182
• Shirota, Y., & Kageyama, H. (2007). Charge Carrier Transporting Molecular Materials and Their Applications in Devices. Chemical Reviews, 107(4), 953–1010. https://doi.org/10.1021/cr050143+
• Sun, Y., Giebink, N. C., Kanno, H., Ma, B., Thompson, M. E., & Forrest, S. R. (2006). Management of singlet and triplet excitons for efficient white organic light-emitting devices. Nature, 440(7086), 908–912. https://doi.org/10.1038/nature04645
• Turhan Irak, Z., & Beytur, M. (2019). Theoretical Study on The Investigation of Antioxidant Properties of Some 4-Benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives. Journal of the Institute of Science and Technology, 9(1), 512–521. https://doi.org/10.21597/jist.481990
• Turhan Irak, Z., & Gumus, S. (2017). Heterotricyclic Compounds Computational Study Click Reaction : 01(07), 80–89.
• Uğurlu, G., & Beytur, M. (2020). Theoretical studies on the structural, vibrational, conformational analysis and nonlinear optic property of 4-(methoxycarbonyl)-phenylboronic acid. Indian Journal of Chemistry -Section A (IJC-A), 59(10), 1504–1512.
• Ulaş, Y. (2020). Experimental and Theoretical Studies of 2- ( naphthalen-1-yl ( piperidin-1-yl ) methyl ) phenol Compound. Journal of the Chemical Society of Pakistan, 42(06), 818–826.
• Ulaş, Y. (2021). Investigation of the relationship between the substituent and nonlinear optical properties in 2- (Phenyl ((4-Vinylphenyl)Amino) Methyl)phenol derivative compounds by DFT method. Journal of the Chemical Society of Pakistan, 43(3), 271–277.
• Ulla, H., Raveendra Kiran, M., Garudachari, B., Satyanarayan, M. N., Umesh, G., & Isloor, A. M. (2014). Blue emitting halogen–phenoxy substituted 1,8-naphthalimides for potential organic light emitting diode applications. Optical Materials, 37, 311–321. https://doi.org/https://doi.org/10.1016/j.optmat.2014.06.016
• Wang, G., Qin, J., Li, C.-R., & Yang, Z. (2015). A highly selective fluorescent probe for Al3+ based on quinoline derivative. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 150, 21–25. https://doi.org/https://doi.org/10.1016/j.saa.2015.05.041
• Wang, Y., Teng, F., Ma, C., Xu, Z., Hou, Y., Yang, S., Wang, Y., & Xu, X. (2004). Green to white to blue OLEDs by using PBD as a chromaticity-tuning layer. Displays, 25(5), 237–239. https://doi.org/https://doi.org/10.1016/j.displa.2004.09.016
• Wu, C., Djurovich, P., & Thompson, M. (2009). Study of Energy Transfer and Triplet Exciton Diffusion in Hole‐Transporting Host Materials. Advanced Functional Materials, 19, 3157–3164. https://doi.org/10.1002/adfm.200900357
• Zhang, X., Guo, X., Chen, Y., Wang, J., Lei, Z., Lai, W., Fan, Q., & Huang, W. (2015). Highly efficient red phosphorescent organic light-emitting devices based on solution-processed small molecular mixed-host. Journal of Luminescence, 161, 300–305. https://doi.org/https://doi.org/10.1016/j.jlumin.2015.01.035
• Zhao, J., Wang, Z., Wang, R., Chi, Z., & Yu, J. (2017). Hybrid white organic light-emitting devices consisting of a non-doped thermally activated delayed fluorescent emitter and an ultrathin phosphorescent emitter. Journal of Luminescence, 184, 287–292. https://doi.org/https://doi.org/10.1016/j.jlumin.2016.11.067
• Zhou, Y., Li, Z.-X., Zang, S.-Q., Zhu, Y.-Y., Zhang, H.-Y., Hou, H.-W., & Mak, T. C. W. (2012). A novel sensitive turn-on fluorescent Zn2+ chemosensor based on an easy to prepare C3-symmetric Schiff-base derivative in 100% aqueous solution. Organic Letters, 14(5), 1214–1217. https://doi.org/10.1021/ol2034417