Skip to main content
SpringerLink
Log in

Synthesis, crystal structure, spectroscopic, hirshfeld surface, DFT and Z-Scan studies of NLO active 2-methylimidazolium 3-nitrophthalate (2MI3NP) single crystal

  • Published:
Journal of Materials Science: Materials in Electronics Aims and scope Submit manuscript

Abstract

The transparent organic crystal of 2-methylimidazolium 3-nitrophthalate (2MI3NP) was grown by the slow-evaporation solution technique. The formation of the title compound was confirmed by NMR, FTIR and Raman studies. The X-ray diffraction studies confirmed that the 2MI3NP crystal belongs to noncentrosymmetric monoclinic space group P21. The density functional theory (DFT/B3LYP 6–311 +  + G(d,p)) approach has been used to do theoretical computations in the ground state. With a successful optimization, theoretical analysis of MEP, NBO, HOMO–LUMO and hyperpolarizability was performed. The grown crystal was thermally stable up to 200 °C after that decomposition point was observed. The UV–Vis-NIR spectrum shows that 2MI3NP has a large transparency (90%) in the entire visible region. Using Tauc's plot, the optical band gap of the crystal was calculated to be 3.35 eV. The temperature-dependent dielectric loss and dielectric constant were determined in the frequency range from 1 to 1 MHz. The Z-scan approach was used to analyse the NLO parameters such as the absorption coefficient (β), nonlinear refractive index (n2) and 3rd order nonlinear susceptibility (χ(3)).

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
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15
Fig. 16
Fig. 17

Similar content being viewed by others

Data availability

This manuscript contains no additional associated data.

References

  1. S. Saha, M.K. Mishra, C.M. Reddy, G.R. Desiraju, Acc. Chem. Res. 51(11), 2957–2967 (2018)

    Article  CAS  Google Scholar 

  2. N.N. Golovnev, M.S. Molokeev, M.K. Lesnikov, I.V. Sterkhova, V.V. Atuchin, J. Mol. Struct. 1149, 367–372 (2017)

    Article  CAS  Google Scholar 

  3. E.R.T. Tiekink, J. Vittal, M. Zaworotko, Organic Crystal Engineering: Frontiers in Crystal Engineering. John Wiley & Sons Ltd (2010). https://doi.org/10.1002/9780470681794

    Article  Google Scholar 

  4. D.M. Turgunalieva, A.L. Stalinskaya, I.I. Kulakov, G.P. Sagitullina, V.V. Atuchin, A.V. Elyshev, I.V. Kulakov, Processes 11(2), 576 (2023)

    Article  CAS  Google Scholar 

  5. G.R. Desiraju, Angew. Chem., Int. Ed. Engl. 34(21), 2311–2327 (1995)

    Article  CAS  Google Scholar 

  6. D.J. Williams, presented at the ACS symposium series 233, Washington, D.C, 1983.

  7. H.S. Nalwa, S. Miyata, Nonlinear optics of organic molecules and polymers. Opt. Eng 36(9), 2622 (1996)

    Article  Google Scholar 

  8. N.N. Golovnev, M.S. Molokeev, M.K. Lesnikov, V.V. Atuchin, J. Phys. Org. Chem. 31(3), e3773 (2018)

    Article  Google Scholar 

  9. A. Ueda, Bull. Chem. Soc. Jpn. 90(11), 1181–1188 (2017)

    Article  CAS  Google Scholar 

  10. C. Lambert, W. Gaschler, G. Nöll, M. Weber, E. Schmälzlin, C. Bräuchle, K. Meerholz, J. Chem. Soc. Perkin Trans. 2(6), 964–974 (2001)

    Article  Google Scholar 

  11. M.H. Shin, S.H. Lee, B.J. Kang, M. Jazbinšek, W. Yoon, H. Yun, F. Rotermund, O.P. Kwon, Adv. Func. Mater. 28(48), 1805257 (2018)

    Article  Google Scholar 

  12. J. Liang, Y. Yan, Y.S. Zhao, Account Mater Res 2(5), 340–351 (2021)

    Article  CAS  Google Scholar 

  13. I.C. Khoo, J. Ding, A. Diaz, Y. Zhang, K. Chen, Mol. Cryst. Liq. Cryst. 375(1), 33–44 (2002)

    Article  CAS  Google Scholar 

  14. Y. Zang, D. Huang, Ca.. Di, D. Zhu, Adv. Mater. 28(22), 4549–4555 (2016)

    Article  CAS  Google Scholar 

  15. S. Taleghani, M. Mirzaei, H. Eshtiagh-Hosseini, A. Frontera, Coord. Chem. Rev. 309, 84–106 (2016)

    Article  CAS  Google Scholar 

  16. B. Hachuła, M. Nowak, J. Kusz, J. Chem. Crystallogr. 40, 201–206 (2010)

    Article  Google Scholar 

  17. T.P. Srinivasan, S. Anandhi, R. Gopalakrishnan, J. Cryst. Growth 318(1), 768–773 (2011)

    Article  CAS  Google Scholar 

  18. C. Glidewell, J.N. Low, J.M. Skakle, J.L. Wardell, Acta Crystallogr. C 59(3), o144–o146 (2003)

    Article  Google Scholar 

  19. S. Chinnasami, R. Paulraj, R. Bhatt, I. Bhaumik, P. Ramasamy, A. Karnal, Opt. Mater. 108, 110380 (2020)

    Article  CAS  Google Scholar 

  20. J. Fuller, R. Carlin, L. Simpson, T. Furtak, Chem. Mater. 7(5), 909–919 (1995)

    Article  CAS  Google Scholar 

  21. S. Chinnasami, P. Rajesh, R. Bhatt, I. Bhaumik, P. Ramasamy, A. Karnal, Optik 243, 167021 (2021)

    Article  CAS  Google Scholar 

  22. C. Sudhakar, M. Saravanabhavan, M. Rajkumar, S. Muhammad, M. Sekar, Chem Sci J 9(190), 2 (2018)

    Google Scholar 

  23. S. Chinnasami, S. Chandran, R. Paulraj, P. Ramasamy, J. Mol. Struct. 1179, 506–513 (2019)

    Article  CAS  Google Scholar 

  24. B. Babu, J. Chandrasekaran, R. Thirumurugan, V. Jayaramakrishnan, K. Anitha, J. Mater. Sci.: Mater. Electron. 28, 1124–1135 (2017)

    CAS  Google Scholar 

  25. R. Mekala, R. Mani, I.B. Rietveld, P. Jagdish, R. Mathammal, H. Jiang, CrystEngComm 18(42), 8194–8206 (2016)

    Article  CAS  Google Scholar 

  26. A. Steephenraj, C. Sidden, R. Paulraj, J. Mater. Sci.: Mater. Electron. 33(29), 22999–23015 (2022)

    CAS  Google Scholar 

  27. T.D. Rani, M. Rajkumar, A. Chandramohan, Opt. Mater. 100, 109614 (2020)

    Article  Google Scholar 

  28. M.D. Bharathi, R. Bhuvaneswari, J. Srividya, G. Vinitha, R. Prithiviraajan, G. Anbalagan, J. Phys. Chem. Solids 113, 50–60 (2018)

    Article  CAS  Google Scholar 

  29. J. Srividya, V. Sivamadhavi, G. Vinitha, G. Anbalagan, Chin. J. Phys. 78, 409–434 (2022)

    Article  CAS  Google Scholar 

  30. https://www.bruker.com/en/products-and-solutions/diffractometers-and-scattering-systems/single-crystal-x-ray-diffractometers/sc-xrd-software/apex.html.

  31. S.R. Yousefi, A. Sobhani, M. Salavati-Niasari, Adv. Powder Technol. 28(4), 1258–1262 (2017)

    Article  CAS  Google Scholar 

  32. C. Dong, J. Appl. Crystallogr. 32(4), 838–838 (1999)

    Article  CAS  Google Scholar 

  33. M.A. Mahdi, S.R. Yousefi, L.S. Jasim, M. Salavati-Niasari, Int. J. Hydrogen Energy 47(31), 14319–14330 (2022)

    Article  CAS  Google Scholar 

  34. John Wiley & Sons, Inc. SpectraBase; SpectraBase Compound ID=26myuuvTxNF https://spectrabase.com/compound/26myuuvTxNF.

  35. John Wiley & Sons, Inc. SpectraBase; SpectraBase Compound ID=7bu5sjHsA21 https://spectrabase.com/compound/7bu5sjHsA21.

  36. S.R. Yousefi, D. Ghanbari, M. Salavati-Niasari, M. Hassanpour, J. Mater. Sci.: Mater. Electron. 27, 1244–1253 (2016)

    CAS  Google Scholar 

  37. P. Mehdizadeh, M. Jamdar, M.A. Mahdi, W.K. Abdulsahib, L.S. Jasim, S.R. Yousefi, M. Salavati-Niasari, Arabian J. Chem. 16(4), 104579 (2023)

    Article  CAS  Google Scholar 

  38. K.R. Santhy, M.D. Sweetlin, S. Muthu, C.S. Abraham, M. Raja, Chem. Data Collect. 24, 100291 (2019)

    Article  CAS  Google Scholar 

  39. N.N. Golovnev, M.S. Molokeev, S.N. Vereshchagin, V.V. Atuchin, M.Y. Sidorenko, M.S. Dmitrushkov, Polyhedron 70, 71–76 (2014)

    Article  CAS  Google Scholar 

  40. N.N. Golovnev, L.A. Solovyov, M.K. Lesnikov, S.N. Vereshchagin, V.V. Atuchin, Inorg. Chim. Acta 467, 39–45 (2017)

    Article  CAS  Google Scholar 

  41. A.S. Raj, S. Chinnasami, R. Paulraj, Chem. Pap. 76(9), 5429–5446 (2022)

    Article  CAS  Google Scholar 

  42. P. Govindasamy, S. Gunasekaran, S. Srinivasan, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 130, 329–336 (2014)

    Article  CAS  Google Scholar 

  43. P. Jena, A. Castleman Jr., Proc. Natl. Acad. Sci. 103(28), 10560–10569 (2006)

    Article  CAS  Google Scholar 

  44. G.L. Eakins, J.S. Alford, B.J. Tiegs, B.E. Breyfogle, C.J. Stearman, J. Phys. Org. Chem. 24(11), 1119–1128 (2011)

    Article  CAS  Google Scholar 

  45. F. De Proft, N. Sablon, D.J. Tozer, P. Geerlings, Faraday Discuss. 135, 151–159 (2007)

    Article  Google Scholar 

  46. D.M. Gil, M.E. Tuttolomondo, A.B. Altabef, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 149, 408–418 (2015)

    Article  CAS  Google Scholar 

  47. C. Sidden, R. Paulraj, P. Parvonraja, M. Murugesan, J. Mol. Struct. 1271, 134047 (2023)

    Article  CAS  Google Scholar 

  48. S. Muthu, J.U. Maheswari, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 92, 154–163 (2012)

    Article  CAS  Google Scholar 

  49. A.E. Reed, F. Weinhold, J. Chem. Phys. 83(4), 1736–1740 (1985)

    Article  CAS  Google Scholar 

  50. S. Chinnasami, R. Paulraj, P. Ramasamy, J. Mol. Struct. 1238, 130448 (2021)

    Article  CAS  Google Scholar 

  51. S. Chinnasami, M. Manikandan, S. Chandran, R. Paulraj, P. Ramasamy, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 206, 340–349 (2019)

    Article  CAS  Google Scholar 

  52. K. Govindarasu, E. Kavitha, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 122, 130–141 (2014)

    Article  CAS  Google Scholar 

  53. M.A. Spackman, D. Jayatilaka, CrystEngComm 11(1), 19–32 (2009)

    Article  CAS  Google Scholar 

  54. M. Wolff, D.J. Grimwood, J.J. McKinnon, M.J. Turner, D. Jayatilaka, M.A. Spackman, Cryst Explor 17, 5 (2012)

    Google Scholar 

  55. M. Ashfaq, K.S. Munawar, M.N. Tahir, N. Dege, M. Yaman, S. Muhammad, S.S. Alarfaji, H. Kargar, M.U. Arshad, ACS Omega 6(34), 22357–22366 (2021)

    Article  CAS  Google Scholar 

  56. K. Boopathi, S.M. Babu, R. Jagan, S. Athimoolam, P. Ramasamy, New J. Chem. 42(21), 17464–17477 (2018)

    Article  CAS  Google Scholar 

  57. N.N. Golovnev, M. Molokeev, S. Vereshchagin, V. Atuchin, J. Coord. Chem. 68(11), 1865–1877 (2015)

    Article  CAS  Google Scholar 

  58. Y.G. Denisenko, M.S. Molokeev, A.S. Oreshonkov, A.S. Krylov, A.S. Aleksandrovsky, N.O. Azarapin, O.V. Andreev, I.A. Razumkova, V.V. Atuchin, Crystals 11(9), 1027 (2021)

    Article  CAS  Google Scholar 

  59. P. Karuppasamy, D.J. Daniel, H. Kim, M.S. Pandian, P. Ramasamy, J. Cryst. Growth 535, 125528 (2020)

    Article  CAS  Google Scholar 

  60. N. Vijayan, M. Vij, K. Thukral, N. Khan, D. Haranath, M. Jayalakshmy, Chin. J. Chem. Eng. 27(3), 701–708 (2019)

    Article  Google Scholar 

  61. S.R. Yousefi, A. Sobhani, H.A. Alshamsi, M. Salavati-Niasari, RSC Adv. 11(19), 11500–11512 (2021)

    Article  CAS  Google Scholar 

  62. V.V. Atuchin, A. Subanakov, A. Aleksandrovsky, B. Bazarov, J. Bazarova, S. Dorzhieva, T. Gavrilova, A. Krylov, M. Molokeev, A. Oreshonkov, Adv. Powder Technol. 28(5), 1309–1315 (2017)

    Article  CAS  Google Scholar 

  63. I.S. Steinberg, A. Kirpichnikov, V. Atuchin, Opt. Mater. 78, 253–258 (2018)

    Article  CAS  Google Scholar 

  64. A. Manohar, V. Vijayakanth, R. Hong, J. Mater. Sci.: Mater. Electron. 31, 799–806 (2020)

    CAS  Google Scholar 

  65. S.R. Yousefi, O. Amiri, M. Salavati-Niasari, Ultrason. Sonochem. 58, 104619 (2019)

    Article  CAS  Google Scholar 

  66. A. Fahad, Z. Abbas, M.F. Zainuddin, S. Jabbar, A.B. Yakubu, Procedia Environ. Sci. 30, 273–278 (2015)

    Article  CAS  Google Scholar 

  67. C. Sidden, R. Paulraj, R. Bhatt, I. Bhaumik, M. Soharab, R. Perumalsamy, J. Phys. Chem. Solids 172, 111065 (2023)

    Article  CAS  Google Scholar 

  68. C. Ji, T. Chen, Z. Sun, Y. Ge, W. Lin, J. Luo, Q. Shi, M. Hong, CrystEngComm 15(11), 2157–2162 (2013)

    Article  CAS  Google Scholar 

  69. M. Mehkoom, M. Faizan, S. Afzal, S. Ahmad, J. Mater. Sci.: Mater. Electron. 32, 28750–28764 (2021)

    CAS  Google Scholar 

  70. R. Ragu, M. Akilan, J. Angelena, P. Latha Mageshwari, S.J. Das, J. Mater. Sci.: Mater. Electron 30, 6287–6299 (2019)

    CAS  Google Scholar 

Download references

Funding

The authors received no funding for this research.

Author information

Authors and Affiliations

  1. Department of Physics and Research Centre, Nanjil Catholic College of Arts and Science, Kaliyakkavilai, Tamilnadu, 629153, India

    Gino D. J & S. Ajitha

  2. Department of Physics, Government Arts College for Men, Krishnagiri, Tamilnadu, 635 001, India

    Chinnasami Sidden

  3. Centre for Crystal Growth, Department of Physics, SSN College of Engineering, Kalavakkam, Tamilnadu, 603110, India

    Rajesh Paulraj

  4. Affiliated to Manonmaniam Sundaranar University, Abishekapatti, Tirunelveli, Tamilnadu, 627012, India

    Gino D. J & S. Ajitha

Authors
  1. Gino D. J
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chinnasami Sidden
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Rajesh Paulraj
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. Ajitha
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

GDJ: Formal analysis, Investigation, Data curation, Writing—Original draft preparation. CS: Experimental Validation, Theoretical Validation, Writing—Reviewing and Editing. RP: Experimental Validation, Conceptualization, Project administration. SA: Funding acquisition, Supervision, Project administration.

Corresponding author

Correspondence to Gino D. J.

Ethics declarations

Conflict of interest

The authors declared no potential conflicts of interest.

Ethical approval

Not applicable

Research involved in human and animal rights

This work does not involve human participants and/or animal.

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 (RTF 74 KB)

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

J, G.D., Sidden, C., Paulraj, R. et al. Synthesis, crystal structure, spectroscopic, hirshfeld surface, DFT and Z-Scan studies of NLO active 2-methylimidazolium 3-nitrophthalate (2MI3NP) single crystal. J Mater Sci: Mater Electron 34, 964 (2023). https://doi.org/10.1007/s10854-023-10362-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10854-023-10362-5

Search

Navigation