Theoretical investigation on the optoelectronic properties of non-centrosymmetric D–A–D hexaazatriphenylene derivatives for photovoltaic applications

Authors

  • El alamy Aziz LCBAE/CMMBA, Faculty of Science, Moulay Ismail University, Meknes, Morocco
  • Amina Amine LCBAE/ CMMBA, Faculty of Science, Moulay Ismail University, Meknes, Morocco
  • Bouzzine Si Mohamed Centre Régional des Métiers d’Education et de Formation, BP 8, Errachida, Morocco http://orcid.org/0000-0002-8008-0711
  • Hamidi Mohamed Equipe d’Electrochimie et Environnement, Faculté des Sciences et Techniques, Université Moulay Ismaïl, B.P. 509 Boutalamine, Errachidia, Morocco
  • Mohammed Bouachrine ESTM, Moulay Ismail University, Meknes, Morocco

DOI:

https://doi.org/10.13171/mjc44/015020713/bouachrine

Abstract

In this work, we report theoretical analysis on the geometries and optoelectronic properties of a family of ambipolar donor-acceptor-donor (D-A-D) as new conjugated compounds based on hexaazatriphenylene (HAT) derivatives synthesized by Rafael Juarezet al.. The theoretical ground-state geometry and electronic structure of the studied molecules were investigated by the density functional theory DFT-B3LYP/6-31G(d).The highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), gap energies and the open-circuit voltage (Voc) of the studied compounds are calculated and discussed.The obtained results show that these compounds can be used in organic photovoltaic devices as an active layer for organic solar cell.

References

Helga Seyler, BalajiPurushothaman, David J. Jones, Andrew B. Holmes, and Wallace W. H. Wong , Pure Appl. Chem. 2012, Vol. 84, No. 4, pp. 1047–1067.

D. J. Gundlach, J. E. Royer, S. K. Park, S. Subramanian, O. D. Jurchescu, B. H. Hamadani, A. J.Moad, R. J. Kline, L. C. Teague, O. Kirillov, C. A. Richter, J. G. Kushmerick, L. J. Richter, S. R.Parkin, T. N. Jackson, J. E. Anthony. Nat. Mater. 2008,7, 216.

S. K. Park, T. N. Jackson, J. E. Anthony, D. A. Mourey. Appl. Phys. Lett. 2007, 91, 063514.

C. D. Simpson, J. Wu, M. D. Watson, and K. M. llen, 1. Mater.Chern.2004, 14, 494.

(a) S. Kitagawa, S. Masaoka, Chem. Rev. 2003, 246, 73–88;

(b) Z.Y. Xiao, X. Zhao, X.K. Jiang, Z.T. Li, Chem. Mater. 2011, 23, 1505–1511.

(a) T. Ishi-I, K. Yaguna, R. Kuwahara, Y. Taguri, S. Mataka. Org. Lett. 2006, 8, 585;

(b) T. Ishi-i, H. Tashiro, R. Kuwahara, S. Mataka, T. Yoshihara, S. Tobita. Chem. Lett. 2006, 35, 158.

Rafael Juarez, Mari M. Ramosand Jose L. Segura. Tetrahedron Letters 48 (2007) 8829–8833.

J.A. Mikroyannidis, D.V. Tsagkournos, P. Balraju, G.D. Sharma. Journal of Power Sources.2011, 196, 4152.

R. Ditchfield, W.J. Hehre, J.A. Pople, J. Chem. Phys. 1971, 54-76.

W.J. Hehre, R. Ditchfiesld, J.A. Pople, J. Chem. Phys. 1972, 56, 643.

P.C. Hariharan, J.A. Pople, Mol. Phys. 1974, 27, 209.

M.S. Gordon, Chem. Phys. Lett. 1980, 76, 33.

M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, Jr. J. A. Montgomery, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, 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, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. Zakrzewski, G. S.Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K.. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, GAUSSIAN 09, Revision B.04, Gaussian: Pittsburgh, PA, 2009.

J. B. Foresman, M. Head-Gordon, J. A. Pople, M. J. Frisch, J. Chem. Phys. 1992, 96, 135.

M. Bouachrine, A. Echchary, S.M. Bouzzine, M. Amine, M. Hamidi M, A. Amine, T. Zair. Phys. Chem. News. 2011, 58 : 61- 66.

L. Yang, J. Feng, A. Ren. Polymer.2005, 46, 10970.

JB. Asbury, YQ. Wang Y, E. Hao, H. Ghosh, T. Lian. Res. ChemIntermed.2001, 27: 393- 406.

(a) Z. Wu, B. Fan, F. Xue, C. Adachi, J. Ouyang, Energy Mater. Sol. Cells.2010, 94, 2230;

(b) A. Gadisa, M. Svensson, M. R. Andersson, O. Inganas. Appl. Phys. Lett. 2004, 84, 1609.

Downloads

Published

2015-06-29

Issue

Vol. 4 No. 4 (2015)

Section

Computational Chemistry

License

Authors who publish with this journal agree to the following terms:

    1. Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal
    2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal
    3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).