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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
https://izlik.org/JA58EH86GA

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
https://izlik.org/JA58EH86GA

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 Article
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
DOI https://doi.org/10.32571/ijct.695754
IZ https://izlik.org/JA58EH86GA
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 1.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):49-59. doi:10.32571/ijct.695754
Chicago Akman, Murat, Ahmet Çağrı Ata, Ümit Yildiko, and İsmail Cakmak. 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.
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 [1]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, June 2020, doi: 10.32571/ijct.695754.
ISNAD Akman, Murat - Ata, Ahmet Çağrı - Yildiko, Ümit - Cakmak, İsmail. “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 1, 2020): 49-59. https://doi.org/10.32571/ijct.695754.
JAMA 1.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, June 2020, pp. 49-59, doi:10.32571/ijct.695754.
Vancouver 1.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. [Internet]. 2020 June 1;4(1):49-5. Available from: https://izlik.org/JA58EH86GA

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