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Prediction of Second-Order Nonlinear Optical Properties of D–π–A Compounds Containing Novel Fluorene Derivatives: A Promising Route to Giant Hyperpolarizabilities

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Abstract

Herein, first attempt has been made to utilize fluorene-based dye-sensitized solar cell (DSSCs) dye JK-201 as potential nonlinear optical (NLO) material and for the theoretical designing of novel NLO chromophores JK-D1–JK-D12. DFT/TDDFT calculations were performed to compute the effect of π-linkers and acceptors-steered modulation on electronic, photophysical and NLO properties of JK-201 and JK-D1–JK-D12. Results illustrate that computed λmax (484.74 nm) and experimentally calculated λmax (481 nm) of JK-201 was found in good agreement. Maximum red shifted absorption spectrum was observed in JK-D12 with 599.38 nm. JK-D1–JK-D12 showed narrow energy gap and broader absorption spectrum as compared to JK-201. NBO analysis confirmed the formation of charge separation state due to robust range of electrons/charge transfer from donor to acceptor via π-bridge. Giant NLO response was observed in all compounds. Particularly, JK-D12 displayed surprisingly large 〈α〉 and βtot computed 1376.74 (a.u.) and 405,731.84 (a.u.) respectively. Although literature is flooded with D–π–A compounds investigated for their DSSCs properties, but research reports on their NLO properties and utilization as NLO materials are completely deserted. Our research will open new horizons to explore DSSCs materials for NLO applications. This theoretical framework also exposed that fluorene-substituted chromophores are excellent NLO candidates for modern hi-tech applications.

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References

  1. M. G. Papadopoulos, A. J. Sadlej, and J. Leszczynski, Non-linear optical properties of matter (Springer, New York, 2006).

    Book  Google Scholar 

  2. M. Akram, M. Adeel, M. Khalid, M. N. Tahir, M. U. Khan, M. A. Asghar, M. A. Ullah, and M. Iqbal (2018). J. Mol. Struct. 1160, 129.

    Article  CAS  Google Scholar 

  3. M. S. Ahmad, M. Khalid, M. A. Shaheen, M. N. Tahir, M. U. Khan, A. A. C. Braga, and H. A. Shad (2017). J. Phys. Chem. Solids 115, 265.

    Article  CAS  Google Scholar 

  4. M. Shahid, M. Salim, M. Khalid, M. N. Tahir, M. U. Khan, and A. A. C. Braga (2018). J. Mol. Struct. 1161, 66.

    Article  CAS  Google Scholar 

  5. Z. Peng and L. Yu (1994). Macromolecules 27, (9), 2638.

    Article  CAS  Google Scholar 

  6. N. Tsutsumi, M. Morishima, and W. Sakai (1998). Macromolecules 31, 7764.

    Article  CAS  Google Scholar 

  7. E. M. Breitung, C.-F. Shu, and R. J. McMahon (2000). J. Am. Chem. Soc. 122, (6), 1154.

    Article  CAS  Google Scholar 

  8. P. S. Halasyamani and W. Zhang, Inorganic Materials for UV and Deep-UV Nonlinear-Optical Applications (ACS Publications, Washington, 2017).

    Book  Google Scholar 

  9. B. Zhang, G. Shi, Z. Yang, F. Zhang, and S. Pan (2017). Angew. Chem. Int. Ed. 56, (14), 3916.

    Article  CAS  Google Scholar 

  10. S. Yamashita (2012). J. Lightwave Technol. 30, (4), 427.

    Article  CAS  Google Scholar 

  11. L. Guo, Z. Guo, and X. Li (2018). J. Mater. Sci.: Mater. Electron. 29, (3), 2577.

    CAS  Google Scholar 

  12. R. D. Fonseca, M. G. Vivas, D. L. Silva, G. Eucat, Y. Bretonnière, C. Andraud, L. De Boni, and C. R. Mendonça (2018). J. Phys. Chem. C 122, (3), 1770.

    Article  CAS  Google Scholar 

  13. P.-H. Sung and T.-F. Hsu (1998). Polymer 39, (6–7), 1453.

    Article  CAS  Google Scholar 

  14. M. Hochberg, T. Baehr-Jones, G. Wang, M. Shearn, K. Harvard, J. Luo, B. Chen, Z. Shi, R. Lawson, and P. Sullivan (2006). Nat. Mater. 5, (9), 703.

    Article  CAS  PubMed  Google Scholar 

  15. P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers (Wiley, New York, 1991).

    Google Scholar 

  16. D. S. Chemla Nonlinear Optical Properties of Organic Molecules and Crystals (Elsevier, Amsterdam, 2012).

    Google Scholar 

  17. B. Nagarajan, S. Kushwaha, R. Elumalai, S. Mandal, K. Ramanujam, and D. Raghavachari (2017). J. Mater. Chem. A 5, (21), 10289.

    Article  CAS  Google Scholar 

  18. X. Dai, B. Dong, M. Ren, and W. Lin (2018). J. Mater. Chem. B 6, 381.

  19. P. Ferdowsi, Y. Saygili, W. Zhang, T. Edvinson, L. Kavan, J. Mokhtari, S. M. Zakeeruddin, M. Grätzel, and A. Hagfeldt (2018). ChemSusChem 11, (2), 494.

    Article  CAS  PubMed  Google Scholar 

  20. S. Yamada, J. Bessho, H. Nakasato, and O. Tsutsumi (2018). Dyes Pigments 150, 89.

    Article  CAS  Google Scholar 

  21. V. Srinivasan, M. Panneerselvam, N. Pavithra, S. Anandan, K. Sundaravel, M. Jaccob, and A. Kathiravan (2017). J. Photochem. Photobiol., A 332, 453.

    Article  CAS  Google Scholar 

  22. S. Haid, M. Marszalek, A. Mishra, M. Wielopolski, J. Teuscher, J. E. Moser, R. Humphry-Baker, S. M. Zakeeruddin, M. Grätzel, and P. Bäuerle (2012). Adv. Funct. Mater. 22, (6), 1291.

    Article  CAS  Google Scholar 

  23. M. R. S. A. Janjua, M. U. Khan, B. Bashir, M. A. Iqbal, Y. Song, S. A. R. Naqvi, and Z. A. Khan (2012). Comput. Theor. Chem. 994, 34.

    Article  CAS  Google Scholar 

  24. M. R. S. A. Janjua, M. Amin, M. Ali, B. Bashir, M. U. Khan, M. A. Iqbal, W. Guan, L. Yan, and Z. M. Su (2012). Eur. J. Inorg. Chem. 2012, (4), 705.

    Article  CAS  Google Scholar 

  25. M. R. S. A. Janjua, Z.-M. Su, W. Guan, C.-G. Liu, L.-K. Yan, P. Song, and G. Maheen (2010). Aust. J. Chem. 63, (5), 836.

    Article  CAS  Google Scholar 

  26. M. R. S. A. Janjua, S. Jamil, A. Mahmood, A. Zafar, M. Haroon, and H. N. Bhatti (2015). Aust. J. Chem. 68, (10), 1502.

    Article  CAS  Google Scholar 

  27. M. R. S. A. Janjua (2012). Inorg. Chem. 51, (21), 11306.

    Article  CAS  PubMed  Google Scholar 

  28. M. R. S. A. Janjua, S. Jamil, T. Ahmad, Z. Yang, A. Mahmood, and S. Pan (2014). Comput. Theor. Chem. 1033, 6.

    Article  CAS  Google Scholar 

  29. M. Haroon, R. Mahmood, and M. R. S. A. Janjua (2017). J. Cluster Sci. 28, (5), 2693.

    Article  CAS  Google Scholar 

  30. M. R. S. A. Janjua, Z. H. Yamani, S. Jamil, A. Mahmood, I. Ahmad, M. Haroon, M. H. Tahir, Z. Yang, and S. Pan (2016). Aust. J. Chem. 69, (4), 467.

    Article  CAS  Google Scholar 

  31. R. Mahmood, M. R. S. A. Janjua, and S. Jamil (2017). J. Cluster Sci. 28, (6), 3175.

    Article  CAS  Google Scholar 

  32. R. N. Almogati, S. G. Aziz, and R. Hilal (2017). J. Theor. Comput. Chem. 16, 1750018.

    Article  CAS  Google Scholar 

  33. R. Hilal, S. G. Aziz, O. I. Osman, and J.-L. Bredas (2017). Mol. Simul. 43, (18), 1523.

    Article  CAS  Google Scholar 

  34. M. U. Khan, M. Khalid, M. Ibrahim, A. A. C. Braga, M. Safdar, A. A. Al-Saadi, and M. R. S. A. Janjua (2018). J. Phys. Chem. C 122, (7), 4009.

    Article  CAS  Google Scholar 

  35. M. U. Khan, M. Ibrahim, M. Khalid, M. S. Qureshi, T. Gulzar, K. M. Zia, A. A. Al-Saadi, and M. R. S. A. Janjua (2018). Chem. Phys. Lett. 715, 222.

  36. S. Paek, H. Choi, H. Choi, C.-W. Lee, M.-S. Kang, K. Song, M. K. Nazeeruddin, and J. Ko (2010). J. Phys. Chem. C 114, (34), 14646.

    Article  CAS  Google Scholar 

  37. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. 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, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, B. E., 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, J. M. 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. J. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, D. 0109, Revision D. 01 (Gaussian, Inc., Wallingford, CT 2009).

  38. Z. Yang, C. Liu, C. Shao, X. Zeng, and D. Cao (2016). Nanotechnology 27, (26), 265701.

    Article  PubMed  CAS  Google Scholar 

  39. Z. Yang, C. Shao, and D. Cao (2015). RSC Adv. 5, (29), 22892.

    Article  CAS  Google Scholar 

  40. J. Autschbach (2009). ChemPhysChem 10, (11), 1757.

    Article  CAS  PubMed  Google Scholar 

  41. A. Dreuw and M. Head-Gordon (2005). Chem. Rev. 105, (11), 4009.

    Article  CAS  PubMed  Google Scholar 

  42. T. Yanai, D. P. Tew, and N. C. Handy (2004). Chem. Phys. Lett. 393, (1), 51.

    Article  CAS  Google Scholar 

  43. V. Barone and M. Cossi (1998). J. Phys. Chem. A 102, (11), 1995.

    Article  CAS  Google Scholar 

  44. A. Karakas, A. Elmali, and H. Unver (2007). Spectrochim. Acta. A Mol. Biomol. Spectrosc. 68, (3), 567.

    Article  PubMed  CAS  Google Scholar 

  45. Z. Yang, C. Liu, C. Shao, C. Lin, and Y. Liu (2015). J. Phys. Chem. C 119, (38), 21852.

    Article  CAS  Google Scholar 

  46. S. Gunasekaran, R. A. Balaji, S. Kumeresan, G. Anand, and S. Srinivasan (2008). Can. J. Anal. Sci. Spectrosc. 53, 149.

    CAS  Google Scholar 

  47. M. Adeel, A. A. Braga, M. N. Tahir, F. Haq, M. Khalid, and M. A. Halim (2017). J. Mol. Struct. 1131, 136.

    Article  CAS  Google Scholar 

  48. M. N. Arshad, A.-A. M. Al-Dies, A. M. Asiri, M. Khalid, A. S. Birinji, K. A. Al-Amry, and A. A. Braga (2017). J. Mol. Struct. 1141, 142.

    Article  CAS  Google Scholar 

  49. M. N. Tahir, M. Khalid, A. Islam, S. M. A. Mashhadi, and A. A. Braga (2017). J. Mol. Struct. 1127, 766.

    Article  CAS  Google Scholar 

  50. S. S. Amiri, S. Makarem, H. Ahmar, and S. Ashenagar (2016). J. Mol. Struct. 1119, 18.

    Article  CAS  Google Scholar 

  51. R. G. Parr, L. V. Szentpaly, and S. Liu (1999). Electrophilicity index. J. Am. Chem. Soc. 121, (9), 1922.

    Article  CAS  Google Scholar 

  52. P. K. Chattaraj, U. Sarkar, and D. R. Roy (2006). Chem. Rev. 106, (6), 2065.

    Article  CAS  PubMed  Google Scholar 

  53. M. Szafran, A. Komasa, and E. Bartoszak-Adamska (2007). J. Mol. Struct. 827, (1), 101.

    Article  CAS  Google Scholar 

  54. C. James, A. A. Raj, R. Reghunathan, V. Jayakumar, and I. H. Joe (2006). J. Raman Spectrosc. 37, (12), 1381.

    Article  CAS  Google Scholar 

  55. C. Qin and A. E. Clark (2007). Chem. Phys. Lett. 438, (1), 26.

    Article  CAS  Google Scholar 

  56. B. S. Mendis and K. N. de Silva (2004). J. Mol. Struct: Theochem. 678, (1), 31.

    Article  CAS  Google Scholar 

  57. D. R. Kanis, M. A. Ratner, and T. J. Marks (1994). Chem. Rev. 94, (1), 195.

    Article  CAS  Google Scholar 

  58. H. S. Nalwa, Handbook of Advanced Electronic and Photonic Materials and Devices: Semiconductors, vol. 1 (Academic Press, Cambridge, 2001).

    Google Scholar 

  59. J.-L. Oudar and D. Chemla (1977). J. Chem. Phys. 66, (6), 2664.

    Article  CAS  Google Scholar 

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Acknowledgments

Ataualpa A. C. Braga, (Grants # 2011/07895-8, 2015/01491-3 and 2014/25770-6) is thankful to Fundação de Amparo à Pesquisa do Estado de São Paulo for financial support. AACB (Grant 309715/2017-2) also thanks the Brazilian National Research Council (CNPq) for financial support and fellowships. This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior—Brasil (CAPES)—Finance Code 001.

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Authors and Affiliations

  1. Department of Applied Chemistry, Government College University, Faisalabad, 38000, Pakistan

    Muhammad Usman Khan & Muhammad Ibrahim

  2. Department of Chemistry, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, 64200, Pakistan

    Muhammad Khalid & Sarfraz Ahmed

  3. Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, Avenida Professor Lineu Prestes, 748, São Paulo, 05508-000, Brazil

    Ataualpa Albert Carmo Braga

  4. Department of Chemistry, University of Education Lahore, Faisalabad Campus, Faisalabad, 38000, Pakistan

    Ayesha Sultan

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  1. Muhammad Usman Khan
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Khan, M.U., Ibrahim, M., Khalid, M. et al. Prediction of Second-Order Nonlinear Optical Properties of D–π–A Compounds Containing Novel Fluorene Derivatives: A Promising Route to Giant Hyperpolarizabilities. J Clust Sci 30, 415–430 (2019). https://doi.org/10.1007/s10876-018-01489-1

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