Skip to main content
SpringerLink
Log in

Theoretical Investigation of Jack-in-the-Box Electro-Optical Compounds: In-Silico Design of Mixed-Argon Benzonitriles Towards the Template of Clusters

  • Original Paper
  • Published:
Journal of Cluster Science Aims and scope Submit manuscript

Abstract

This work was inspired by a previous report (Janjua et al. J. Phys. Chem. A 113, 3576–3587, 2009) in which the nonlinear-optical (NLO) response strikingly improved with an increase in the conjugation path. Herein, the effect of donor and acceptor substitutions on the geometrical parameters, electronic, optical and reactivity of argon in organic matrices has been computed by computational methods. The 6–311 ++ g(2d,2p) basis set and second order Moller–Plesset perturbation theory are used to explore mixed-argon benzonitrile compounds (1–7) namely; hydrogen argon cyanide, methyl argon cyanide, phenyl argon cyanide, cyano-phenyl argon cyanide, hydroxy-phenyl argon cyanide, nitro-phenyl argon cyanide and methoxy-phenyl argon cyanide respectively. Mullikan population analysis, natural bonding orbital (NBO) analysis, frontier molecular orbital analysis, molecular electrostatic potential surface analysis, polarizability and hyperpolarizability of noble gases in organic matrices have been studied. The results indicate that the electron donating groups (hydroxy, methoxy, phenyl and methyl) and electron withdrawing groups (nitro and cyano) fine tune the HOMO–LUMO orbitals and nonlinear optical properties. NBO analysis confirmed that these donor–acceptor groups support the charge transfer in our investigated jack-in-the-box compounds. The linear polarizability and first hyperpolarizability results suggest that all the studied compounds are good candidates for NLO response and associated applications.

Graphic Abstract

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. K. Ariga, J. P. Hill, M. V. Lee, A. Vinu, R. Charvet, and S. Acharya (2008). Sci Technol Adv Mater. https://doi.org/10.1088/1468-6996/9/1/014109.

    Article  PubMed  PubMed Central  Google Scholar 

  2. G. V. Oshovsky, D. N. Reinhoudt, and W. Verboom (2007). Angew. Chem. Int. Ed. 46 (14), 2366–2393.

    Article  CAS  Google Scholar 

  3. E. Fischer (1894). Ber. Dtsch. Chem. Grs. 27 (3), 3479–3483.

    Article  CAS  Google Scholar 

  4. L. Khriachtchev, M. Räsänen, and R. B. Gerber (2009). Acc. Chem. Res. 42 (1), 183–191.

    Article  CAS  Google Scholar 

  5. J. Kalinowski, R. B. Gerber, M. Räsänen, A. Lignell, and L. Khriachtchev (2014). J. Chem. Phys. 140 (9), 094303.

    Article  Google Scholar 

  6. J.-M. Lehn (1993). Science 260 (5115), 1762–1764.

    Article  CAS  Google Scholar 

  7. W. Luck and O. Schrems (1980). Spectrosc. Lett. 13 (10), 719–728.

    Article  CAS  Google Scholar 

  8. A. Lignell, L. Khriachtchev, M. Pettersson, and M. Räsänen (2003). J. Chem. Phys. 118 (24), 11120–11128.

    Article  CAS  Google Scholar 

  9. A. Lignell, L. Khriachtchev, H. Lignell, and M. Räsänen (2006). Phys. Chem. Chem. Phys. 8 (21), 2457–2463.

    Article  CAS  Google Scholar 

  10. 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, 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, 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, and D. J. Fox, D. 0109, Revision D. 01 (Gaussian Inc, Wallingford, 2009).

    Google Scholar 

  11. R. Dennington, T. Keith, and J. Millam, GaussView, version 5 (Semichem Inc., Shawnee Mission, 2009).

    Google Scholar 

  12. Ghiasuddin, 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, 129–141.

    Article  CAS  Google Scholar 

  13. M. S. Ahmad, M. Khalid, M. A. Shaheen, M. N. Tahir, M. U. Khan, A. A. C. Braga, and H. A. Shad (2018). J. Phys. Chem. Solids 115, 265–276.

    Article  CAS  Google Scholar 

  14. M. Shahid, M. Salim, M. Khalid, M. N. Tahir, M. U. Khan, and A. A. C. Braga (2018). J. Mol. Struct. 1161, 66–75.

    Article  CAS  Google Scholar 

  15. R. Jawaria, M. Hussain, M. Khalid, M. U. Khan, M. N. Tahir, M. M. Naseer, A. A. C. Braga, and Z. Shafiq (2019). Synthesis. Inorg. Chim. Acta 486, 162–171.

    Article  CAS  Google Scholar 

  16. M. Khalid, M. A. Ullah, M. Adeel, M. U. Khan, M. N. Tahir, and A. A. C. Braga (2019). J. Saudi Chem. Soc. 23 (5), 546–560.

    Article  CAS  Google Scholar 

  17. M. N. Tahir, S. H. Mirza, M. Khalid, A. Ali, M. U. Khan, and A. A. C. Braga (2019). J. Mol. Struct. 1180, 119–126.

    Article  CAS  Google Scholar 

  18. M. Haroon, M. Khalid, T. Akhtar, M. N. Tahir, M. U. Khan, M. Saleem, and R. Jawaria (2019). J. Mol. Struct. 1187, 164–171.

    Article  CAS  Google Scholar 

  19. M. Rafiq, M. Khalid, M. N. Tahir, M. U. Ahmad, M. U. Khan, M. M. Naseer, A. A. C. Braga, and Z. Shafiq (2019). Appl. Organomet. Chem. 33, e5182.

    Article  CAS  Google Scholar 

  20. B. Khan, M. Khalid, M. R. Shah, M. N. Tahir, M. U. Khan, A. Ali, and S. Muhammad (2019). Efficient Synthesis by Mono-Carboxy Methylation of 4, 4′-Biphenol. ChemistrySelect 4 (32), 9274–9284.

    Article  CAS  Google Scholar 

  21. A. Hussain, M. U. Khan, M. Ibrahim, M. Khalid, A. Ali, S. Hussain, M. Saleem, N. Ahmad, S. Muhammad, and A. G. Al-Sehemi (2020). J. Mol. Struct. 1201, 127183.

    Article  Google Scholar 

  22. M. Srnec and E. I. Solomon (2017). J. Am. Chem. Soc. 139 (6), 2396–2407.

    Article  CAS  Google Scholar 

  23. R. Hussain, M. U. Khan, M. Y. Mehboob, M. Khalid, J. Iqbal, K. Ayub, M. Adnan, M. Ahmed, K. Atiq, and K. Mahmood (2020). ChemistrySelect 5 (17), 5022–5034.

    Article  CAS  Google Scholar 

  24. R. A. Shehzad, J. Iqbal, M. U. Khan, R. Hussain, H. M. A. Javed, A. U. Rehman, M. U. Alvi, and M. Khalid (2020). Comp. Theor. Chem. 1181, 112833.

    Article  CAS  Google Scholar 

  25. M. Y. Mehboob, R. Hussain, M. U. Khan, M. Adnan, A. Umar, M. U. Alvi, M. Ahmed, M. Khalid, J. Iqbal, and M. N. Akhtar (2020). Theor. Chem. 1186, 112908.

    Article  CAS  Google Scholar 

  26. Z. Afzal, R. Hussain, M. U. Khan, M. Khalid, J. Iqbal, M. U. Alvi, M. Adnan, M. Ahmed, M. Y. Mehboob, and M. Hussain (2020). J. Mol. Model. 26 (6), 137–137.

    Article  CAS  Google Scholar 

  27. G. Mahalakshmi and V. Balachandran (2015). Spectrochim. Acta. A Mol. Biomol. Spectrosc. 135, 321–334.

    Article  CAS  Google Scholar 

  28. M. R. S. A. Janjua (2012). Inorg. Chem. 51 (21), 11306–11314.

    Article  CAS  Google Scholar 

  29. M. Mutailipu, Z. Xie, X. Su, M. Zhang, Y. Wang, Z. Yang, M. R. S. A. Janjua, and S. Pan (2017). J. Am. Chem. Soc. 139 (50), 18397–18405.

    Article  CAS  Google Scholar 

  30. 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), 4009–4018.

    Article  CAS  Google Scholar 

  31. M. R. S. A. Janjua, M. U. Khan, B. Bashir, M. A. Iqbal, Y. Song, S. A. R. Naqvi, and Z. A. Khan (2012). Comp. Theor. Chem. 994, 34–40.

    Article  CAS  Google Scholar 

  32. 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), 705–711.

    Article  CAS  Google Scholar 

  33. 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 (2019). Chem. Phys. Lett. 715, 222–230.

    Article  CAS  Google Scholar 

  34. M. U. Khan, M. Ibrahim, M. Khalid, A. A. C. Braga, S. Ahmed, and A. Sultan (2019). J. Cluster Sci. 30 (2), 415–430.

    Article  CAS  Google Scholar 

  35. M. U. Khan, M. Ibrahim, M. Khalid, S. Jamil, A. A. Al-Saadi, and M. R. S. A. Janjua (2019). Chem. Phys. Lett. 719, 59–66.

    Article  CAS  Google Scholar 

  36. M. R. S. A. Janjua (2021). Inorg. Chem. 60 (4), 2816–2828.

    Article  CAS  Google Scholar 

  37. M. R. S. A. Janjua, R. Mahmood, M. Haroon, F. Anwar, M. U. Khan, and N. Ullah (2021). J Clust Sci. https://doi.org/10.1007/s10876-021-01997-7.

    Article  Google Scholar 

  38. M. R. S. A. Janjua (2020). Chem Eur J. https://doi.org/10.1002/chem.202004299.

    Article  Google Scholar 

  39. M. Haroon and M. R. S. A. Janjua (2020). Mater Today Commun. https://doi.org/10.1016/j.mtcomm.2020.101880.

    Article  Google Scholar 

  40. A. Karakas, A. Elmali, and H. Unver (2007). Spectrochim. Acta. A Mol. Biomol. Spectrosc. 68 (3), 567–572.

    Article  Google Scholar 

Download references

Acknowledgements

The authors are thankful to the University of Sargodha, Pakistan and the Cornell University, USA for providing all the computational resources to complete this research article.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Sargodha, Sargodha, 40100, Pakistan

    Nargis Sultana, Muhammad Ilyas Tariq, Urooj Siddique & Maria Farooq

  2. Department of Chemistry, University of Okara, Okara, 56300, Pakistan

    Muhammad Usman Khan

  3. Department of Materials Science and Engineering, Cornell University, Ithaca, NY, 14853, USA

    Saba Jamil

  4. Super Light Materials and Nanotechnology Laboratory, Department of Chemistry, University of Agriculture, Faisalabad, 38000, Pakistan

    Saba Jamil

  5. Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran, 31261, Kingdom of Saudi Arabia

    Muhammad Ramzan Saeed Ashraf Janjua

Authors
  1. Nargis Sultana
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Muhammad Ilyas Tariq
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Urooj Siddique
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Maria Farooq
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Muhammad Usman Khan
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Saba Jamil
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Muhammad Ramzan Saeed Ashraf Janjua
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Muhammad Ilyas Tariq or Muhammad Ramzan Saeed Ashraf Janjua.

Additional information

Publisher's Note

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

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 1496 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sultana, N., Tariq, M.I., Siddique, U. et al. Theoretical Investigation of Jack-in-the-Box Electro-Optical Compounds: In-Silico Design of Mixed-Argon Benzonitriles Towards the Template of Clusters. J Clust Sci 33, 1185–1192 (2022). https://doi.org/10.1007/s10876-021-02052-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10876-021-02052-1

Keywords

Search

Navigation