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Vol. 36 No. 9 (2024): Vol 36 Issue 9, 2024

Copyright (c) 2024 Dr Brahamdutt Arya, Manisha, Vijay Dangi

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Theoretical Studies on Reactivity Indices, Electronic, Optical and Thermodynamics Properties of Pentacene-Tetrapyrrole Derivatives using DFT Method

https://doi.org/10.14233/ajchem.2024.31686
Manisha
Department of Chemistry, Baba Mastnath University, Asthal Bohar, Rohtak-124021, India
https://orcid.org/0009-0008-6292-4782
Vijay Dangi
Department of Chemistry, Baba Mastnath University, Asthal Bohar, Rohtak-124021, India
https://orcid.org/0000-0002-1343-6845
Brahamdutt Arya
Y & Y Nanotech Solutions Pvt. Ltd., Rohtak-124001, India; Department of Higher Education, Sector-5, Shiksha Sadan, Panchkula-134114, India
https://orcid.org/0000-0002-8264-690X

Corresponding Author(s) : Brahamdutt Arya

brahmdattarya@gmail.com

Asian Journal of Chemistry, Vol. 36 No. 9 (2024): Vol 36 Issue 9, 2024

Abstract

A detailed theoretical analysis of the electronic properties, reactivity indices, optical and thermodynamic properties of pentacene-tetrapyrrole (PTP) molecules utilizing the DFT and TD-DFT methods at 6-311(d,p) basis set is conducted. The thermodynamic properties and molecule electrostatic potential were computed using the DFT/B3LYP/6-311(d,p) technique. The electronic properties, reactivity indices and optical properties were determined using the TD-DFT/6-311(d,p) at several functionals: B3LYP, CAM-B3LYP, B3PW91, PBEPBE and WB97XD. The change in electronic properties, reactivity indices, optical and thermodynamic properties were also investigated with variation in the position of the –NH group at the pentacene’s periphery from inward to outward and central benzene ring of pentacene with nitrogen containing cyclic rings such as pyrrole in pentacene-tetrapyrrole derivatives.

Keywords

Pentacene-Tetrapyrrole molecules DFT TD-DFT Optoelectronic Thermodynamic Pentacene
Manisha, Dangi, V., & Arya, B. (2024). Theoretical Studies on Reactivity Indices, Electronic, Optical and Thermodynamics Properties of Pentacene-Tetrapyrrole Derivatives using DFT Method. Asian Journal of Chemistry, 36(9), 1988–2000. https://doi.org/10.14233/ajchem.2024.31686
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References
  1. C. Sutton, J.S. Sears, V. Coropceanu and J.-L. Brédas, J. Phys. Chem. Lett., 4, 919 (2013); https://doi.org/10.1021/jz3021292
  2. K. Bouchouit, Z. Sofiani, B. Derkowska, S. Abed, N. Benali-Cherif, M. Bakasse and B. Sahraoui, Opt. Commun., 278, 180 (2007); https://doi.org/10.1016/j.optcom.2007.05.068
  3. K. Bouchouit, Z. Essaidi, S. Abed, A. Migalska-Zalas, B. Derkowska, N. Benali-cherif, M. Mihaly, A. Meghea and B. Sahraoui, Chem. Phys. Lett., 455, 270 (2008); https://doi.org/10.1016/j.cplett.2008.02.101
  4. K. Bouchouit, H. Bougharraf, B. Derkowska-Zielinska, N. Benali-cherif and B. Sahraoui, Opt. Mater., 48, 215 (2015); https://doi.org/10.1016/j.optmat.2015.07.035
  5. F. Aziz, M. Hassan Sayyad, K. Sulaiman, B.H. Majlis, K.S. Karimov, Z. Ahmad and G. Sugandi, Meas. Sci. Technol., 23, 014001 (2012); https://doi.org/10.1088/0957-0233/23/1/014001
  6. M. Murugavelu, P.K.M. Imran, K.R. Sankaran and S. Nagarajan, Mater. Sci. Semicond. Process., 16, 461 (2013); https://doi.org/10.1016/j.mssp.2012.08.001
  7. Y. Che, X. Yang, G. Liu, C. Yu, H. Ji, J. Zuo, J. Zhao and L. Zang, J. Am. Chem. Soc., 132, 5743 (2010); https://doi.org/10.1021/ja909797q
  8. M. Guan, L. Li, G. Cao, Y. Zhang, B. Wang, X. Chu, Z. Zhu and Y. Zeng, Org. Electron., 12, 2090 (2011); https://doi.org/10.1016/j.orgel.2011.09.003
  9. H.-R. Tseng, H. Phan, C. Luo, M. Wang, L.A. Perez, S.N. Patel, L. Ying, E.J. Kramer, T.-Q. Nguyen, G.C. Bazan and A.J. Heeger, Adv. Mater., 26, 2993 (2014); https://doi.org/10.1002/adma.201305084
  10. L. Xiao-Hong, C. Hong-Ling, Z. Rui-Zhou and Z. Xian-Zhou, Spectrochim. Acta A Mol. Biomol. Spectrosc., 137, 321 (2015); https://doi.org/10.1016/j.saa.2014.08.036
  11. M. Yoosuf Ameen, T. Abhijith, S. De, S.K. Ray and V.S. Reddy, Org. Electron., 14, 554 (2013); https://doi.org/10.1016/j.orgel.2012.12.012
  12. Z. Liu, M. Kobayashi, B.C. Paul, Z. Bao and Y. Nishi, Phys. Rev. B Condens. Matter Mater. Phys., 82, 035311 (2010); https://doi.org/10.1103/PhysRevB.82.035311
  13. M. Ball, Y. Zhong, Y. Wu, C. Schenck, F. Ng, M. Steigerwald, S. Xiao and C. Nuckolls, Acc. Chem. Res., 48, 267 (2015); https://doi.org/10.1021/ar500355d
  14. W. Pisula, X. Feng and K. Müllen, Chem. Mater., 23, 554 (2011); https://doi.org/10.1021/cm102252w
  15. Z. Sun, Q. Ye, C. Chi and J. Wu, Chem. Soc. Rev., 41, 7857 (2012); https://doi.org/10.1039/c2cs35211g
  16. W. Chen, X. Li, G. Long, Y. Li, R. Ganguly, M. Zhang, N. Aratani, H. Yamada, M. Liu and Q. Zhang, Angew. Chem., 130, 13743 (2018); https://doi.org/10.1002/ange.201808779
  17. J. Li, S. Chen, Z. Wang and Q. Zhang, Chem. Rec., 16, 1518 (2016); https://doi.org/10.1002/tcr.201600015
  18. R. Rieger and K. Müllen, J. Phys. Org. Chem., 23, 315 (2010); https://doi.org/10.1002/poc.1644
  19. A. Narita, X.-Y. Wang, X. Feng and K. Müllen, Chem. Soc. Rev., 44, 6616 (2015); https://doi.org/10.1039/C5CS00183H
  20. Z. Sun and J. Wu, J. Mater. Chem., 22, 4151 (2012); https://doi.org/10.1039/C1JM14786B
  21. P.-Y. Gu, Y. Zhao, J.-H. He, J. Zhang, C. Wang, Q.-F. Xu, J.-M. Lu, X.W. Sun and Q. Zhang, J. Org. Chem., 80, 3030 (2015); https://doi.org/10.1021/jo5027707
  22. P.Y. Gu, Z. Wang, G. Liu, H. Yao, Z. Wang, Y. Li, J. Zhu, S. Li and Q. Zhang, Chem. Mater., 29, 4172 (2017); https://doi.org/10.1021/acs.chemmater.7b01318
  23. L. Ji, A. Friedrich, I. Krummenacher, A. Eichhorn, H. Braunschweig, M. Moos, S. Hahn, F.L. Geyer, O. Tverskoy, J. Han, C. Lambert, A. Dreuw, T.B. Marder and U.H.F. Bunz, J. Am. Chem. Soc., 139, 15968 (2017); https://doi.org/10.1021/jacs.7b09460
  24. M. Richter, K.S. Schellhammer, P. Machata, G. Cuniberti, A. Popov, F. Ortmann, R. Berger, K. Müllen and X. Feng, Org. Chem. Front., 4, 847 (2017); https://doi.org/10.1039/C7QO00180K
  25. Z. Wang, P. Gu, G. Liu, H. Yao, Y. Wu, Y. Li, G. Rakesh, J. Zhu, H. Fu and Q. Zhang, Chem. Commun., 53, 7772 (2017); https://doi.org/10.1039/C7CC03898D
  26. A. Mateo-Alonso, Chem. Soc. Rev., 43, 6311 (2014); https://doi.org/10.1039/C4CS00119B
  27. U.H.F. Bunz, Acc. Chem. Res., 48, 1676 (2015); https://doi.org/10.1021/acs.accounts.5b00118
  28. A. Irfan, A.R. Chaudhary, S. Muhammad, A.G. Al-Sehemi, H. Bo, M.W. Mumtaz and M.A. Qayyum, Results Phys., 11, 599 (2018); https://doi.org/10.1016/j.rinp.2018.09.052
  29. V.M. Vidya and P. Chetti, J. Phys. Org. Chem., 34, e4128 (2021); https://doi.org/10.1002/poc.4128
  30. N.N. Tri, L.V. Duong and M.T. Nguyen, Mater. Today Commun., 24, 101054 (2020); https://doi.org/10.1016/j.mtcomm.2020.101054
  31. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X.Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N.J. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K.Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J. B. Foresman, J.V. Ortiz, J. Cioslowski and D.J. Fox, Gaussian 09, Gaussian, Inc., Wallingford CT (2009).
  32. N.M. O’boyle, A.L. Tenderholt and K.M. Langner, J. Comput. Chem., 29, 839 (2008); https://doi.org/10.1002/jcc.20823
  33. O.E. Oyeneyin, Phys. Sci. Int. J., 16, 1 (2017); https://doi.org/10.9734/PSIJ/2017/36555
  34. M.F. Khan, R.B. Rashid, M.A. Hossain and M.A. Rashid, Dhaka Univ. J. Pharm. Sci., 16, 1 (2017); https://doi.org/10.3329/dujps.v16i1.33376
  35. K.K. Srivastava, S. Srivastava and T. Alam, Pelagia Res. Libr., 5, 288 (2014).
  36. J.L. Gázquez, A. Cedillo and A. Vela, J. Phys. Chem. A, 111, 1966 (2007); https://doi.org/10.1021/jp065459f
  37. P.K. Chattaraj, A. Chakraborty and S. Giri, J. Phys. Chem. A, 113, 10068 (2009); https://doi.org/10.1021/jp904674x
  38. R. Contreras, J. Andres, V.S. Safont, P. Campodonico and J.G. Santos, J. Phys. Chem. A, 107, 5588 (2003); https://doi.org/10.1021/jp0302865
  39. A. Cedillo, R. Contreras, M. Galván, A. Aizman, J. Andrés and V.S. Safont, J. Phys. Chem. A, 111, 2442 (2007); https://doi.org/10.1021/jp068459o
  40. P. Jaramillo, P. Pérez, R. Contreras, W. Tiznado and P. Fuentealba, J. Phys. Chem. A, 110, 8181 (2006); https://doi.org/10.1021/jp057351q
  41. P. Campodonico, J.G. Santos, J. Andres and R. Contreras, J. Phys. Org. Chem., 17, 273 (2004); https://doi.org/10.1002/poc.719
  42. T. Karakurt, M. Dinçer, A. Çetin and M. Sekerci, Spectrochim. Acta A Mol. Biomol. Spectrosc., 77, 189 (2010); https://doi.org/10.1016/j.saa.2010.05.006
  43. J. Zhang, Y.-H. Kan, H.-B. Li, Y. Geng, Y. Wu and Z.-M. Su, Dyes Pigments, 95, 313 (2012); https://doi.org/10.1016/j.dyepig.2012.05.020
  44. R.G. Parr, R.A. Donnelly, M. Levy and W.E. Palke, J. Chem. Phys., 68, 3801 (1978); https://doi.org/10.1063/1.436185
  45. R.G. Pearson, J. Am. Chem. Soc., 85, 3533 (1963); https://doi.org/10.1021/ja00905a001
  46. R.G. Parr and R.G. Pearson, J. Am. Chem. Soc., 105, 7512 (1983); https://doi.org/10.1021/ja00364a005
  47. R.G. Parr, L. Szentpály and S. Liu, J. Am. Chem. Soc., 121, 1922 (1999); https://doi.org/10.1021/ja983494x
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