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

TR EN

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

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

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.

Details

Primary Language

English

Subjects

Chemical Engineering

Journal Section

Research Article

Authors

Murat Akman This is me
0000-0003-3345-6445
Türkiye

Ahmet Çağrı Ata ^*
0000-0002-2296-2265
Türkiye

Ümit Yildiko
Türkiye

İsmail Cakmak This is me
Türkiye

Publication Date

June 30, 2020

Submission Date

February 27, 2020

Acceptance Date

May 5, 2020

Published in Issue

Year 2020 Volume: 4 Number: 1

DOI

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

IZ

https://izlik.org/JA58EH86GA

Cite

RIS / Bibtex

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.Murat Akman, Ahmet Çağrı Ata, Ümit Yildiko, İsmail Cakmak. Molecular structure, frontier molecular orbitals, NBO, MESP and thermodynamic properties of 5,12-dibromo perylene with DFT calculation methods. Int. J. Chem. Technol. 2020 Jun. 1;4(1):49-5. doi:10.32571/ijct.695754

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Abstract

Keywords

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

Abstract

Keywords

References

Details

Primary Language

Subjects

Journal Section

Authors

Publication Date

Submission Date

Acceptance Date

Published in Issue

DOI

IZ

Cite

Cited By

Investigation of novel diethanolamine dithiocarbamate agent for RAFT polymerization: DFT computational study of the oligomer molecules

Computational Investigation of 5.5'',7''-trihydroxy-3,7-dimethoxy-4'-4''-O-biflavone from Flavonoids Using DFT Calculations and Molecular Docking

Dietanol Amin Ditiyokarbamat RAFT Ajanının 1H ve 13C NMR Spektrumlarının Teorik İncelenmesi

DFT CALCULATIONS AND MOLECULAR DOCKING STUDY IN 6-(2”-PYRROLIDINONE-5”-YL)-(-) EPICATECHIN MOLECULE FROM FLAVONOIDS

Synthesis, and characterization of Ni(II), and Cu(II) metal complexes containing new azo dye ligand (N,N,N) and evaluation of their biological activities supported by DFT studies, molecular docking, ADMET profiling, drug-likeness analysis and toxicity prediction

Applying choline chloride-based hydrophilic deep eutectic solvents for separation of acetonitrile-water solutions: effect of hydrogen bond donor contribution in performance