SpringerLink
Log in

Computational analysis of the structural, optoelectronic and photovoltaic properties of triphenylamine-based dyes and their interaction with TiO2 / Iodine

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In this work, six molecules M1-M6, with the donor—π-spacer—acceptor structure, based on triphenylamine have been purposely studied to be applied in π-type dye-sensitized solar cells (DSSCs). We explore the effect of different electron-withdrawing substituents on the optoelectronic, structural, and photovoltaic dye properties. The key parameters of all the dyes affecting the power conversion efficiency (PCE) were theoretically investigated in detail using density functional theory (DFT) and TD-BHandHLYP calculations to reveal structure–property relationships. The calculated results show that the strong electron-withdrawing groups of thienothiadiazole and furano-thiadiazole, reduce energy gaps and provide a red shift of absorption spectra. The dye M1 and M3 have presented interesting optoelectronic properties with interesting charge transfer properties. Meanwhile, the enhanced free energy of charge injection (∆Ginject) and light-harvesting efficiency of the M5 dye revealed that this dye can be used as a potential sensitizer for TiO2-based DSSCs. The DFT method is also used to evaluate the bond interactions between the dye and iodine. The results suggest that dyes containing thienothiadiazole and furano-thiadiazole as π-spacers show more stable interactions with iodine species, thereby increasing the concentration of the redox couple at the surface of the semiconductor. In addition, the process of charge transfer and dye adsorption on (TiO2)9 cluster was investigated. Calculations show that the M3 dye has lower adsorption energy than the corresponding M1 dye. These results suggest that the adsorption of M3 on the TiO2 semiconductor would be more stable. The results indicate that the selected dyes provide promising results and motivate future investigations on these new systems.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (France)

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

Data availability

All data are available and mainly the Cartesian coordinates of all the studied dyes.

References

  1. M.S. Dresselhaus, I.L. Thomas, Nature 414, 332 (2001)

    Article  CAS  PubMed  Google Scholar 

  2. E.W.-G. Diau, ACS Energy Lett. 2, 334 (2017)

    Article  CAS  Google Scholar 

  3. B. O’Regan, M. Grätzel, Nature 353, 737 (1991)

    Article  Google Scholar 

  4. T. Higashino, H. Imahori, Dalton Trans. 44, 448 (2014)

    Article  Google Scholar 

  5. A. Yella, C.-L. Mai, S.M. Zakeeruddin, S.-N. Chang, C.-H. Hsieh, C.-Y. Yeh, M. Grätzel, Angew. Chem. Int. Ed. 53, 2973 (2014)

    Article  CAS  Google Scholar 

  6. M. Urbani, M. Grätzel, M.K. Nazeeruddin, T. Torres, Chem. Rev. 114, 12330 (2014)

    Article  CAS  PubMed  Google Scholar 

  7. W.M. Campbell, K.W. Jolley, P. Wagner, K. Wagner, P.J. Walsh, K.C. Gordon, L. Schmidt-Mende, M.K. Nazeeruddin, Q. Wang, M. Grätzel, D.L. Officer, J. Phys. Chem. C 111, 11760 (2007)

    Article  CAS  Google Scholar 

  8. T. Bessho, S.M. Zakeeruddin, C.-Y. Yeh, E.W.-G. Diau, M. Grätzel, Angew. Chem. Int. Ed. 49, 6646 (2010)

    Article  CAS  Google Scholar 

  9. S. Mathew, A. Yella, P. Gao, R. Humphry-Baker, B.F.E. Curchod, N. Ashari-Astani, I. Tavernelli, U. Rothlisberger, M.K. Nazeeruddin, M. Grätzel, Nat. Chem. 6, 242 (2014)

    Article  CAS  PubMed  Google Scholar 

  10. M.-E. Ragoussi, M. Ince, T. Torres, Eur. J. Org. Chem. 2013, 6475 (2013)

    Article  CAS  Google Scholar 

  11. G.C. Vougioukalakis, A.I. Philippopoulos, T. Stergiopoulos, P. Falaras, Coord. Chem. Rev. 255, 2602 (2011)

    Article  CAS  Google Scholar 

  12. K.-M. Lee, S.-J. Wu, C.-Y. Chen, C.-G. Wu, M. Ikegami, K. Miyoshi, T. Miyasaka, K.-C. Ho, J. Mater. Chem. 19, 5009 (2009)

    Article  CAS  Google Scholar 

  13. S.-Q. Fan, C. Kim, B. Fang, K.-X. Liao, G.-J. Yang, C.-J. Li, J.-J. Kim, J. Ko, J. Phys. Chem. C 115, 7747 (2011)

    Article  CAS  Google Scholar 

  14. K. Hara, T. Sato, R. Katoh, A. Furube, T. Yoshihara, M. Murai, M. Kurashige, S. Ito, A. Shinpo, S. Suga, H. Arakawa, Adv. Funct. Mater. 15, 246 (2005)

    Article  CAS  Google Scholar 

  15. L. Kloo, Chem. Commun. 49, 6580 (2013)

    Article  CAS  Google Scholar 

  16. H. Spanggaard, F.C. Krebs, Sol. Energy Mater. Sol. Cells 83, 125 (2004)

    Article  CAS  Google Scholar 

  17. H. Chen, H. Huang, X. Huang, J.N. Clifford, A. Forneli, E. Palomares, X. Zheng, L. Zheng, X. Wang, P. Shen, B. Zhao, S. Tan, J. Phys. Chem. C 114, 3280 (2010)

    Article  CAS  Google Scholar 

  18. H. Choi, I. Raabe, D. Kim, F. Teocoli, C. Kim, K. Song, J.-H. Yum, J. Ko, M.K. Nazeeruddin, M. Grätzel, Chem. Eur. J. 16, 1193 (2010)

    Article  CAS  PubMed  Google Scholar 

  19. S. Namuangruk, R. Fukuda, M. Ehara, J. Meeprasert, T. Khanasa, S. Morada, T. Kaewin, S. Jungsuttiwong, T. Sudyoadsuk, V. Promarak, J. Phys. Chem. C 116, 25653 (2012)

    Article  CAS  Google Scholar 

  20. C. Li, J.-H. Yum, S.-J. Moon, A. Herrmann, F. Eickemeyer, N.G. Pschirer, P. Erk, J. Schöneboom, K. Müllen, M. Grätzel, M.K. Nazeeruddin, Chemsuschem 1, 615 (2008)

    Article  CAS  PubMed  Google Scholar 

  21. Y. Shibano, T. Umeyama, Y. Matano, H. Imahori, Org. Lett. 9, 1971 (2007)

    Article  CAS  PubMed  Google Scholar 

  22. F. De Angelis, Chem. Phys. Lett. 493, 323 (2010)

    Article  Google Scholar 

  23. K. Hara, K. Sayama, Y. Ohga, A. Shinpo, S. Suga, and H. Arakawa, Chem. Commun. 569 (2001).

  24. Z.-S. Wang, Y. Cui, K. Hara, Y. Dan-oh, C. Kasada, A. Shinpo, Adv. Mater. 19, 1138 (2007)

    Article  CAS  Google Scholar 

  25. K. Hara, T. Sato, R. Katoh, A. Furube, Y. Ohga, A. Shinpo, S. Suga, K. Sayama, H. Sugihara, H. Arakawa, J. Phys. Chem. B 107, 597 (2003)

    Article  CAS  Google Scholar 

  26. Z.-S. Wang, Y. Cui, Y. Dan-oh, C. Kasada, A. Shinpo, K. Hara, J. Phys. Chem. C 112, 17011 (2008)

    Article  CAS  Google Scholar 

  27. K. Hara, M. Kurashige, Y. Dan-oh, C. Kasada, A. Shinpo, S. Suga, K. Sayama, H. Arakawa, New J. Chem. 27, 783 (2003)

    Article  CAS  Google Scholar 

  28. K. Hara, Y. Tachibana, Y. Ohga, A. Shinpo, S. Suga, K. Sayama, H. Sugihara, H. Arakawa, Sol. Energy Mater. Sol. Cells 77, 89 (2003)

    Article  CAS  Google Scholar 

  29. A. Abbotto, L. Beverina, R. Bozio, S. Bradamante, C. Ferrante, G.A. Pagani, R. Signorini, Adv. Mater. 12, 1963 (2000)

    Article  CAS  Google Scholar 

  30. L.L. Estrella, S.H. Lee, D.H. Kim, Dyes Pigments 165, 1 (2019)

    Article  CAS  Google Scholar 

  31. Z.M.E. Fahim, S.M. Bouzzine, Y. Ait Aicha, M. Bouachrine, M. Hamidi, Res. Chem. Intermed. 44, 2009 (2018)

    Article  CAS  Google Scholar 

  32. B. Xu, E. Sheibani, P. Liu, J. Zhang, H. Tian, N. Vlachopoulos, G. Boschloo, L. Kloo, A. Hagfeldt, L. Sun, Adv. Mater. 26, 6629 (2014)

    Article  CAS  PubMed  Google Scholar 

  33. N. Blouin, A. Michaud, M. Leclerc, Adv. Mater. 19, 2295 (2007)

    Article  CAS  Google Scholar 

  34. J. Li, F. Dierschke, J. Wu, A.C. Grimsdale, K. Müllen, J. Mater. Chem. 16, 96 (2006)

    Article  CAS  Google Scholar 

  35. Q. Li, L. Lu, C. Zhong, J. Shi, Q. Huang, X. **, T. Peng, J. Qin, Z. Li, J. Phys. Chem. B 113, 14588 (2009)

    Article  CAS  PubMed  Google Scholar 

  36. D. Kim, M.-S. Kang, K. Song, S.O. Kang, J. Ko, Tetrahedron 64, 10417 (2008)

    Article  CAS  Google Scholar 

  37. T. Horiuchi, H. Miura, K. Sumioka, S. Uchida, J. Am. Chem. Soc. 126, 12218 (2004)

    Article  CAS  PubMed  Google Scholar 

  38. S. Ito, H. Miura, S. Uchida, M. Takata, K. Sumioka, P. Liska, P. Comte, P. Péchy, and M. Grätzel, Chem. Commun. 5194 (2008).

  39. D. Kuang, S. Uchida, R. Humphry-Baker, S.M. Zakeeruddin, M. Grätzel, Angew. Chem. Int. Ed. 47, 1923 (2008)

    Article  CAS  Google Scholar 

  40. A. Hagfeldt, G. Boschloo, L. Sun, L. Kloo, H. Pettersson, Chem. Rev. 110, 6595 (2010)

    Article  CAS  PubMed  Google Scholar 

  41. K. Srinivas, K. Yesudas, K. Bhanuprakash, V.J. Rao, L. Giribabu, J. Phys. Chem. C 113, 20117 (2009)

    Article  CAS  Google Scholar 

  42. G. Wang, S. Miao, Q. Zhang, H. Liu, H. Li, N. Li, Q. Xu, J. Lu, L. Wang, Chem. Commun. 49, 9470 (2013)

    Article  CAS  Google Scholar 

  43. M. Guo, M. Li, Y. Dai, W. Shen, J. Peng, C. Zhu, S.H. Lin, R. He, RSC Adv. 3, 17515 (2013)

    Article  CAS  Google Scholar 

  44. L. Malak, H. Toufik, S.M. Bouzzine, H. Bih, F. Lamchouri 02, 23 (2018)

    Google Scholar 

  45. Y.S. Yang, H.D. Kim, J.-H. Ryu, K.K. Kim, S.S. Park, K.-S. Ahn, J.H. Kim, Synth. Met. 161, 850 (2011)

    Article  CAS  Google Scholar 

  46. P. Shen, X. Liu, S. Jiang, L. Wang, L. Yi, D. Ye, B. Zhao, S. Tan, Dyes Pigments 92, 1042 (2012)

    Article  CAS  Google Scholar 

  47. W. Wu, J. Zhang, H. Yang, B. **, Y. Hu, J. Hua, C. **g, Y. Long, H. Tian, J. Mater. Chem. 22, 5382 (2012)

    Article  CAS  Google Scholar 

  48. M. Lazrak, H. Toufik, S.M. Bouzzine, H. Bih, F. Lamchouri, I.O.P. Conf, Ser. Earth Environ. Sci. 161, 012021 (2018)

    Google Scholar 

  49. S.P. Singh, M.S. Roy, A. Thomas, K. Bhanuprakash, G.D. Sharma, Org. Electron. 13, 3108 (2012)

    Article  CAS  Google Scholar 

  50. H. Jia, X. Ju, M. Zhang, Z. Ju, H. Zheng, Phys. Chem. Chem. Phys. 17, 16334 (2015)

    Article  CAS  PubMed  Google Scholar 

  51. W. Lee, J. Choi, J.W. Namgoong, S.H. Kim, K.C. Sun, S.H. Jeong, K. Yoo, M.J. Ko, J.P. Kim, Dyes Pigments 104, 185 (2014)

    Article  CAS  Google Scholar 

  52. J. He, J. Hua, G. Hu, X.J. Yin, H. Gong, C. Li, Dyes Pigments 104, 75 (2014)

    Article  CAS  Google Scholar 

  53. J.T. Lin, P.-C. Chen, Y.-S. Yen, Y.-C. Hsu, H.-H. Chou, M.-C.P. Yeh, Org. Lett. 11, 97 (2009)

    Article  CAS  PubMed  Google Scholar 

  54. K.D. Seo, I.T. Choi, H.K. Kim, Chem. Eur. J. 21, 14804 (2015)

    Article  CAS  PubMed  Google Scholar 

  55. R. Li, X. Lv, D. Shi, D. Zhou, Y. Cheng, G. Zhang, P. Wang, J. Phys. Chem. C 113, 7469 (2009)

    Article  CAS  Google Scholar 

  56. A. Hagfeldt, M. Grätzel, Acc. Chem. Res. 33, 269 (2000)

    Article  CAS  PubMed  Google Scholar 

  57. M.K. Nazeeruddin, A. Kay, I. Rodicio, R. Humphry-Baker, E. Mueller, P. Liska, N. Vlachopoulos, M. Graetzel, J. Am. Chem. Soc. 115, 6382 (1993)

    Article  CAS  Google Scholar 

  58. J. Preat, D. Jacquemin, E.A. Perpète, Environ. Sci. Technol. 44, 5666 (2010)

    Article  CAS  PubMed  Google Scholar 

  59. R. Katoh, A. Furube, T. Yoshihara, K. Hara, G. Fujihashi, S. Takano, S. Murata, H. Arakawa, M. Tachiya, J. Phys. Chem. B 108, 4818 (2004)

    Article  CAS  Google Scholar 

  60. J.B. Asbury, Y.-Q. Wang, E. Hao, H.N. Ghosh, T. Lian, Res. Chem. Intermed. 27, 393 (2001)

    Article  CAS  Google Scholar 

  61. A. Mahmood, M. H. Tahir, A. Irfan, A. G. Al-Sehemi, and M. S. Al-Assiri, Comput. Theor. Chem. Complete, 94 (2015).

  62. T. Marinado, K. Nonomura, J. Nissfolk, Martin. K. Karlsson, D. P. Hagberg, L. Sun, S. Mori, and A. Hagfeldt, Langmuir 26, 2592 (2010).

  63. S. Rühle, M. Greenshtein, S.-G. Chen, A. Merson, H. Pizem, C.S. Sukenik, D. Cahen, A. Zaban, J. Phys. Chem. B 109, 18907 (2005)

    Article  PubMed  Google Scholar 

  64. W. Sang-aroon, S. Laopha, P. Chaiamornnugool, S. Tontapha, S. Saekow, V. Amornkitbamrung, J. Mol. Model. 19, 1407 (2013)

    Article  CAS  PubMed  Google Scholar 

  65. Gaussian 09, Revision A.02, M. J. Frisch, G. W. Trucks, 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, Inc., Wallingford CT (2016).

  66. J. Preat, C. Michaux, D. Jacquemin, E.A. Perpète, J. Phys. Chem. C 113, 16821 (2009)

    Article  CAS  Google Scholar 

  67. Z. Fahim, S. M. Bouzzine, A. Youssef, M. Bouachrine, and M. Hamidi, Comput. Theor. Chem. 1125, (2018).

  68. R. Tarsang, V. Promarak, T. Sudyoadsuk, S. Namuangruk, S. Jungsuttiwong, J. Photochem. Photobiol. Chem. 273, 8 (2014)

    Article  CAS  Google Scholar 

  69. H. Toufik, S.M. Bouzzine, F. Lamchouri, M. Nawdali, M. Hamidi, M. Bouachrine, J. Mater. Environ. Sci. 3, 286 (2012)

    CAS  Google Scholar 

  70. M. Lazrak, H. Toufik, S.M. Bouzzine, F. Lamchouri, Res. Chem. Intermed. 46, 3961 (2020)

    Article  CAS  Google Scholar 

  71. M. Grätzel, Nature 414, 338 (2001)

    Article  PubMed  Google Scholar 

  72. S.U.-D. Khan, A. Mahmood, U.A. Rana, S. Haider, Theor. Chem. Acc. 134, 1596 (2014)

    Article  Google Scholar 

  73. S. Ennehary, H. Toufik, M. Lazrak, S.M. Bouzzine, F. Lamchouri, J. Mol. Model. 27, 122 (2021)

    Article  CAS  PubMed  Google Scholar 

  74. M.A.M. Rashid, D. Hayati, K. Kwak, J. Hong, Nanomaterials 10, 914 (2020)

    Article  PubMed  PubMed Central  Google Scholar 

  75. G. Deogratias, O.S. Al-Qurashi, N. Wazzan, T. Pogrebnaya, A. Pogrebnoi, J. Mol. Model. 26, 288 (2020)

    Article  CAS  PubMed  Google Scholar 

  76. S. Ennehary, H. Toufik, S.M. Bouzzine, F. Lamchouri, J. Comput. Electron. 19, 840 (2020)

    Article  CAS  Google Scholar 

  77. S. El Mzioui, S. M. Bouzzine, M. Bourass, M. Naciri Bennani, and M. Hamidi, J. Comput. Electron. 18, 951 (2019).

  78. M. **e, J. Wang, F.-Q. Bai, L. Hao, H.-X. Zhang, Dyes Pigments 120, 74 (2015)

    Article  CAS  Google Scholar 

  79. M. **e, F.-Q. Bai, J. Wang, C.-P. Kong, J. Chen, H.-X. Zhang, Comput. Mater. Sci. 111, 239 (2016)

    Article  CAS  Google Scholar 

  80. W. Zierkiewicz, M. Michalczyk, S. Scheiner, Molecules 23, 1416 (2018)

    Article  PubMed  PubMed Central  Google Scholar 

  81. S. Ito, S.M. Zakeeruddin, R. Humphry-Baker, P. Liska, R. Charvet, P. Comte, M.K. Nazeeruddin, P. Péchy, M. Takata, H. Miura, S. Uchida, M. Grätzel, Adv. Mater. 18, 1202 (2006)

    Article  CAS  Google Scholar 

  82. H. Kusama, K. Sayama, Phys. Chem. Chem. Phys. 17, 4379 (2015)

    Article  CAS  PubMed  Google Scholar 

  83. H. Kusama, H. Sugihara, K. Sayama, J. Phys. Chem. C 115, 2544 (2011)

    Article  CAS  Google Scholar 

  84. Z. Liu, K. Duan, H. Guo, Y. Deng, H. Huang, X. Yi, H. Chen, S. Tan, Dyes Pigments 140, 312 (2017)

    Article  CAS  Google Scholar 

  85. H. Chen, Y. Gong, Á. Vázquez-Mayagoitia, J. Zhang, J.M. Cole, A.C.S. Appl, Energy Mater. 3, 423 (2020)

    CAS  Google Scholar 

  86. J.K. Roy, S. Kar, J. Leszczynski, Sci. Rep. 8, 10997 (2018)

    Article  PubMed  PubMed Central  Google Scholar 

  87. R. Sánchez-de-Armas, M.A. San-Miguel, J. Oviedo, J. Fdez, Sanz. J. Chem. Phys. 136, 194702 (2012)

    Article  PubMed  Google Scholar 

Download references

Acknowledgments

Realized with the support of the National Center for Scientific and Technical Research (CNRST—Morocco) as part of the Research Excellence Awards Program (No. 28USMBA2017).

Funding

Polydisciplinary Faculty of Taza, Sidi Mohamed Ben Abdellah University, Taza, Morocco.

Author information

Authors and Affiliations

  1. Laboratory of Natural Substances, Pharmacology, Environment, Modeling, Health and Quality of Life (SNAMOPEQ), Polydisciplinary Faculty of Taza, Sidi Mohamed Ben Abdellah University, Fez, Morocco

    Malak Lazrak, Hamid Toufik, Sliman Ennehary, Si Mohamed Bouzzine & Fatima Lamchouri

  2. Regional Center for Training and Professional Education, BP 8, Errachidia, Morocco

    Si Mohamed Bouzzine

Authors
  1. Malak Lazrak
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hamid Toufik
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sliman Ennehary
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Si Mohamed Bouzzine
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Fatima Lamchouri
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

M.L. did most of the practical work as part of a PhD thesis supervised by H.T. and prepared the manuscript. H.T. designed and coordinated the study, participated in article preparation, corrected the manuscript and edited the final version and submitted it for publication. S.E. contributed to data analysis. F.L. and S.M.B. participated in study design, helped to improve the manuscript and critically revised the manuscript. All authors read and approved the final manuscript.

Corresponding author

Correspondence to Hamid Toufik.

Ethics declarations

Conflict of interest

The authors declare no conflict of interests.

Ethical approval

Not applicable.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lazrak, M., Toufik, H., Ennehary, S. et al. Computational analysis of the structural, optoelectronic and photovoltaic properties of triphenylamine-based dyes and their interaction with TiO2 / Iodine. Res Chem Intermed 49, 1855–1878 (2023). https://doi.org/10.1007/s11164-023-04988-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-023-04988-7

Keywords

Search

Navigation