Molecular structure, frontier molecular orbitals, NBO, MESP and thermodynamic properties of 5,12-dibromo perylene with DFT calculation methods

Murat Akman; Ahmet Çağrı Ata; Ümit Yildiko; İsmail Cakmak

doi:10.32571/ijct.695754

Research Article

5,12-Dibromo Perilenin DFT Hesaplama Yöntemleri ile Moleküler Yapısı, Sınır Moleküler Orbitalleri, NBO, MESP ve Termodinamik Özellikleri

Year 2020, Volume: 4 Issue: 1, 49 - 59, 30.06.2020

Murat Akman Ahmet Çağrı Ata , Ümit Yildiko , İsmail Cakmak

https://doi.org/10.32571/ijct.695754

Cited By: 5

Abstract

Perilen-3,4,9,10-tetrakarboksilik dianhidrit (PTCDA) uzun yıllardır endüstriyel pigmentler olarak kullanılmaktadır. Bu Perspektif, PTCDA türevlerinin sentez ve fiziksel özelliklerinin ve bunların organik elektronikteki uygulamalarının belirlenmesini önemli kılmaktadır. Gaz fazında, 5,12-Dibromoperyilen bileşiğinin kuantum kimyasal çalışması, yoğunluk fonksiyonu teorisi (DFT) -B3LYP yönteminin temel LanL2DZ ve 6-311G seti kullanılarak gerçekleştirildi. 1H-NMR, 13C-NMR, HOMO-LUMO analizi, dipol momenti, moleküler elektrostatik yüzey potansiyeli (MESP) ve molekülün doğal orbital bağı (NBO) analizi yapıldı. Sonuçlar grafikler, tablolar ve şekillerle gösterilmiştir. 1H-NMR, 13C-NMR sonuçlarının deneysel değerlerle karşılaştırılmasında B3LYP 6-311G daha başarılı sonuçlar verdi. Bileşiğin doğrusal olmayan özellikleri belirlendi.

Keywords

PTCDA Türevleri, DBP, DFT, LanL2DZ

References

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Molecular structure, frontier molecular orbitals, NBO, MESP and thermodynamic properties of 5,12-dibromo perylene with DFT calculation methods

Year 2020, Volume: 4 Issue: 1, 49 - 59, 30.06.2020

Murat Akman Ahmet Çağrı Ata , Ümit Yildiko , İsmail Cakmak

https://doi.org/10.32571/ijct.695754

Cited By: 5

Abstract

Perylene-3,4,9,10-tetracarboxylic dianhydride (PTCDA) has been used as industrial pigments for many years. This perspective makes it important to determine the synthesis and physical properties of PTCDA derivatives and their functional properties for application as electron acceptors in organic transistors. In the gas phase, the quantum chemical study of the 5,12-dibromoperylene compound was performed using the basic set of LanL2DZ and 6-311G of the density function theory (DFT)-B3LYP method. Because basic set of LanL2DZ and 6-311G of the density function theory (DFT)-B3LYP method are predicted to yield more efficient and verifiable results than others. 1H-NMR, 13C-NMR, HOMO-LUMO analysis, dipole moment, molecular electrostatic surface potential (MESP) and natural orbital bond (NBO) analysis of the molecule were carried out. The results were shown with graphs, tables and figures. In the comparison of 1H-NMR, 13C-NMR results with the experimental values, B3LYP 6-311G gave more successful results. The nonlinear optical properties of the compound were determined.

Keywords

PTCDA Derivatives, DBP, DFT, LanL2DZ

References

1. Paredes-Gil, K.; Mendizabal, F.; Páez-Hernández, D.; Arratia-Pérez, R. Comput. Mater. Sci. 2017, 126, 514-527.
2. Kolcu, F.; Çulhaoğlu, S.; Kaya, İ. Prog. Org. Coat. 2019, 137, 105284.
3. Kucinska, M.; Frac, I.; Ulanski, J.; Makowski, T.; Nosal, A.; Gazicki-Lipman, M. Synth. Met. 2019, 250, 12-19.
4. Dong, D.; Li, Q.; Hou, W.; Zhang, H. J. Mol. Struct. 2020, 1199, 127002.
5. Cao, L.; Xu, L.; Zhang, D.; Zhou, Y.; Zheng, Y.; Fu, Q.; Jiang, X.-F.; Lu, F. Chem. Phys. Lett. 2017, 682, 133-139.
6. Otero, R.; Vázquez De Parga, A. L.; Gallego, J. M. Surf. Sci. Rep. 2017, 72 (3), 105-145.
7. Dere, A. Physica B Condens. Matter. 2018, 547, 127-133.
8. Veerababu, M.; Kothandaraman, R. Electrochim. Acta. 2017, 232, 244-253.
9. Djurišić, A. B.; Fritz, T.; Leo, K. Opt. Commun. 2000, 183 (1), 123-132.
10. Farag, A. A. M.; Osiris, W. G.; Yahia, I. S. Synth. Met. 2011, 161 (17), 1805-1812.
11. Büyükekşi, S. I; Orman, E. B.; Acar, N.; Altındal, A.; Özkaya, A. R.; Şengül, A. Dyes Pigments 2019, 161, 66-78.
12. Ozser, M. E.; Mohiuddin, O. J. Mol. Struct. 2018, 1158, 145-155.
13. Lathiotakis, N. N.; Kerkines, I. S. K.; Theodorakopoulos, G.; Petsalakis, I. D. Chem. Phys. Lett. 2018, 691, 388-393.
14. Cabir, B.; Yildiko, U.; Ağirtaş, M. S. J. Coord. Chem. 2019, 72 (17), 2997-3011.
15. Basma, A.-K.; Dinleyici, M.; Abourajab, A.; Kök, C.; Bodapati, J. B.; Uzun, D.; Koyuncu, S.; Icil, H. J Photoch Photobio A. 2020, 393, 112432..
16. Solğun, D. G.; Keskin, M. S.; Yıldıko, Ü.; Ağırtaş, M. S. Chem .Pap. 2020, 74, 2389-2401.
17. M. J. Frisch, G. W. T., H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, And D. J. Fox, Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford Ct, 2016.
18. Khajehzadeh, M.; Moghadam, M. Spectrochim. Acta A: 2017, 180, 51-66.
19. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157 (3), 200-206.
20. Hertwig, R. H.; Koch, W. Chem. Phys. Lett. 1997, 268 (5-6), 345-351.
21. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82 (1), 270-283.
22. Ülküseven, B.; Bal-Demirci, T.; Akkurt, M.; Yalçın, Ş. P.; Büyükgüngör, O. Polyhedron 2008, 27 (18), 3646-3652.
23. Akkurt, M.; Yalçın, Ş.; Gürsoy, E.; Ulusoy Güzeldemirci, N.; Büyükgüngör, O. Acta Crystallogr. E. 2007, 63, O3103.
24. Matussek, M.; Filapek, M.; Gancarz, P.; Krompiec, S.; Grzegorz Małecki, J.; Kotowicz, S.; Siwy, M.; Maćkowski, S.; Chrobok, A.; Schab-Balcerzak, E.; Słodek, A. Dyes Pigments 2018, 159, 590-599.
25. Li, H.; Meng, J.; Sun, X. Inorg. Chem. Commun. 2019, 105, 194-198.
26. Huang, C.; Barlow, S.; Marder, S. R. J. Org. Chem. 2011, 76 (8), 2386-2407.
27. Pakseresht, M.; Bodapati, J. B.; Icil, H. J. Photochem. Photobiol. A. 2018, 360, 270-277.
28. Wu, S.; Cheng, C.; Hou, W.; Li, Q.; Dong, D.; Gao, Y.; Liu, L.; Liang, B.; Zhang, H. Tetrahedron 2019, 75 (41), 130577.
29. Yuen, J. D.; Pozdin, V. A.; Young, A. T.; Turner, B. L.; Giles, I. D.; Naciri, J.; Trammell, S. A.; Charles, P. T.; Stenger, D. A.; Daniele, M. A. Dyes Pigments 2019, 108014.
30. Piosik, E.; Synak, A.; Martyński, T. Spectrochim. Acta A: Mol. Biomol. Spectrosc. 2018, 189, 374-380.
31. Pekdemir, F.; Orman, E. B.; Selçuki, N. A.; Özkaya, A. R.; Salih, B.; Şengül, A. J. Photochem. Photobiol. A 2019, 379, 54-6.

There are 31 citations in total.

Details

Primary Language	English
Subjects	Chemical Engineering
Journal Section	Research Articles
Authors	Murat Akman This is me 0000-0003-3345-6445 Ahmet Çağrı Ata 0000-0002-2296-2265 Ümit Yildiko İsmail Cakmak This is me
Publication Date	June 30, 2020
Published in Issue	Year 2020 Volume: 4 Issue: 1

Cite

APA	Akman, M., Ata, A. Ç., Yildiko, Ü., Cakmak, İ. (2020). Molecular structure, frontier molecular orbitals, NBO, MESP and thermodynamic properties of 5,12-dibromo perylene with DFT calculation methods. International Journal of Chemistry and Technology, 4(1), 49-59. https://doi.org/10.32571/ijct.695754
AMA	Akman M, Ata AÇ, Yildiko Ü, Cakmak İ. Molecular structure, frontier molecular orbitals, NBO, MESP and thermodynamic properties of 5,12-dibromo perylene with DFT calculation methods. Int. J. Chem. Technol. June 2020;4(1):49-59. doi:10.32571/ijct.695754
Chicago	Akman, Murat, Ahmet Çağrı Ata, Ümit Yildiko, and İsmail Cakmak. “Molecular Structure, Frontier Molecular Orbitals, NBO, MESP and Thermodynamic Properties of 5,12-Dibromo Perylene With DFT Calculation Methods”. International Journal of Chemistry and Technology 4, no. 1 (June 2020): 49-59. https://doi.org/10.32571/ijct.695754.
EndNote	Akman M, Ata AÇ, Yildiko Ü, Cakmak İ (June 1, 2020) Molecular structure, frontier molecular orbitals, NBO, MESP and thermodynamic properties of 5,12-dibromo perylene with DFT calculation methods. International Journal of Chemistry and Technology 4 1 49–59.
IEEE	M. Akman, A. Ç. Ata, Ü. Yildiko, and İ. Cakmak, “Molecular structure, frontier molecular orbitals, NBO, MESP and thermodynamic properties of 5,12-dibromo perylene with DFT calculation methods”, Int. J. Chem. Technol., vol. 4, no. 1, pp. 49–59, 2020, doi: 10.32571/ijct.695754.
ISNAD	Akman, Murat et al. “Molecular Structure, Frontier Molecular Orbitals, NBO, MESP and Thermodynamic Properties of 5,12-Dibromo Perylene With DFT Calculation Methods”. International Journal of Chemistry and Technology 4/1 (June 2020), 49-59. https://doi.org/10.32571/ijct.695754.
JAMA	Akman M, Ata AÇ, Yildiko Ü, Cakmak İ. Molecular structure, frontier molecular orbitals, NBO, MESP and thermodynamic properties of 5,12-dibromo perylene with DFT calculation methods. Int. J. Chem. Technol. 2020;4:49–59.
MLA	Akman, Murat et al. “Molecular Structure, Frontier Molecular Orbitals, NBO, MESP and Thermodynamic Properties of 5,12-Dibromo Perylene With DFT Calculation Methods”. International Journal of Chemistry and Technology, vol. 4, no. 1, 2020, pp. 49-59, doi:10.32571/ijct.695754.
Vancouver	Akman M, Ata AÇ, Yildiko Ü, Cakmak İ. Molecular structure, frontier molecular orbitals, NBO, MESP and thermodynamic properties of 5,12-dibromo perylene with DFT calculation methods. Int. J. Chem. Technol. 2020;4(1):49-5.