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Crystal structure and third-order nonlinear optical properties of supramolecular cocrystals of 18-crown-6 with 5-aminoisophthalic acid

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Abstract

Self-assembled supramolecular cocrystals of 18-crown-6.2(5-aminoisophthalic acid) have been synthesized from 18-crown-6 (18C6) and 5-aminoisophthalic acid (5AIPA) (stoichiometric ratio 1:2). The single-crystal X-ray analysis revealed the crystal structure, indicating a monoclinic system with the centrosymmetric space group C2/m. The assembly of the supramolecular structure primarily relies on N–H···O and O–H···O interactions. Characteristic functional groups were identified using FT-IR and micro-Raman spectral analyses. Additionally, the diffuse reflectance spectrum estimated a direct bandgap energy of 2.84 eV. The cocrystal exhibited fluorescent emission in the solid state at room temperature as observed in photoluminescence studies. Analysis utilizing Hirshfeld surface and fingerprint plots unveiled close contacts resulting from robust interactions in the crystal packing. The third-order nonlinear optical properties of the crystal grown were determined using a single-beam Z-scan technique.

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All data generated or analyzed during this study are included in this published article (and its supplementary information files).

References

  1. S. Basu, Ind. Eng. Chem. Prod. Res. Dev. 23(2), 183–186 (1984)

    Article  CAS  Google Scholar 

  2. O. Ostroverkhova, Chem. Rev. 116(22), 13279–13412 (2016)

    Article  CAS  PubMed  Google Scholar 

  3. C.Y. Liu, A.J. Bard, Acc. Chem. Res. 32(3), 235–245 (1999)

    Article  CAS  Google Scholar 

  4. S. Kar, R. Bhatt, V. Shukla, R.K. Choubey, P. Sen, K.S. Bartwal, Solid State Commun. 137(6), 283–287 (2006)

    Article  CAS  Google Scholar 

  5. P.S. Patil, M. Shkir, S.R. Maidur, S. AlFaify, M. Arora, S.V. Rao, H. Abbas, V Ganesh Opt. Mater. 72, 427–435 (2017)

    Article  CAS  Google Scholar 

  6. B. Riscob, M. Shakir, J. Kalyana Sundar, S. Natarajan, M.A. Wahab, G. Bhagavannarayana, Spectrochim Acta Part. A 78(1), 543–548 (2011)

    Article  CAS  Google Scholar 

  7. H. Huang, G. Deng, J. Liu, J. Wu, P. Si, H. Xu, S. Bo, L. Qiu, Z. Zhen, X. Liu, Dyes Pigm. 99(3), 753–758 (2013)

    Article  CAS  Google Scholar 

  8. S. Omar, M. Shkir, S. AlFaify, V. Ganesh, H. Algarni, P.S. Nayab, M. Arora, Opt. Quantum Electron. 50, 1–16 (2018)

    Article  CAS  Google Scholar 

  9. M. Manonmani, C. Balakrishnan, S. Rafi Ahamed, G. Vinitha, S.P. Meenakshisundaram, R.M. Sockalingam, J. Mol. Struct. 1190, 1–10 (2019)

    Article  CAS  Google Scholar 

  10. C.R. Wie, Mater. Sci. Eng. R. 13(1), 1–56 (1994)

    Article  Google Scholar 

  11. R.K. Choubey, P. Sen, S. Kar, G. Bhagavannarayana, K.S. Bartwal, Solid State Commun. 140(3–4), 120–124 (2006)

    Article  CAS  Google Scholar 

  12. S. Kar, R.K. Choubey, P. Sen, G. Bhagavannarayana, K.S. Bartwal, Condens. Matter. 393(1–2), 37–42 (2007)

    CAS  Google Scholar 

  13. J.Z. Ge, X.Q. Fu, T. Hang, Q. Ye, R.G. Xiong, Cryst. Growth Des. 10(8), 3632–3637 (2010)

    Article  CAS  Google Scholar 

  14. C. Ji, Z. Sun, S. Zhang, S. Zhao, T. Chen, Y. Tang, J. Luo, Chem. Comm. 51(12), 2298–2300 (2015)

    Article  CAS  PubMed  Google Scholar 

  15. Y. Zhang, H.Y. Ye, D.W. Fu, R.G. Xiong, Angew Chem. Int. Ed. 126(8), 2146–2150 (2014)

    Article  Google Scholar 

  16. Y.Z. Tang, Y.M. Yu, J.B. Xiong, Y.H. Tan, H.R. Wen, J. Am. Chem. Soc. 137(41), 13345–13351 (2015)

    Article  CAS  PubMed  Google Scholar 

  17. M.E. Lines, A.M. Glass, Principles and Application of Ferroelectrics and Related Materials (Oxford University Press, 1977)

  18. M. Lallart (ed.), Ferroelectrics: Applications (BoD–Books on Demand, 2011)

  19. H.Y. Ye, S.H. Li, Y. Zhang, L. Zhou, F. Deng, R.G. Xiong, J. Am. Chem. Soc. 136(28), 10033–10040 (2014)

    Article  CAS  PubMed  Google Scholar 

  20. D.W. Fu, W. Zhang, H.L. Cai, Y. Zhang, J.Z. Ge, R.G. Xiong, S.D. Huang, J. Am. Chem. Soc. 133(32), 12780–12786 (2011)

    Article  CAS  PubMed  Google Scholar 

  21. N.D. Boardman, T. Munshi, I.J. Scowena, C.C. Seaton, Acta Crystallogr. Sect. B Struct. Sci. 70, 132–140 (2014)

    Article  CAS  Google Scholar 

  22. Y.A. Simonov, M.S. Fonar’, V.C. Kravtsov, J. Lipkowski, E.V. Ganin, A.A. Yavolovskii, Crystallogr. Rep. 47, 86–93 (2002)

    Article  CAS  Google Scholar 

  23. B.R. Bhogala, A. Nangia, Cryst. Growth Des. 6, 32–35 (2006)

    Article  CAS  Google Scholar 

  24. C. Balakrishnan, M. Manonmani, S. Sivaraman, R. Markkandan, S.R. Ahamed, G. Vinitha, S.P. Meenakshisundaram, R.M. Sockalingam, J. Mol. Struct. 1201, 127158 (2020)

    Article  CAS  Google Scholar 

  25. C. Balakrishnan, M. Manonmani, S.R. Ahamed, G. Vinitha, S.P. Meenakshisundaram, J. Mol. Struct. 1277, 134853 (2023)

    Article  CAS  Google Scholar 

  26. C. Balakrishnan, M. Manonmani, S. Rafi Ahamed, G. Vinitha, S. Meenakshisundaram, R. Sockalingam, Acta Cryst. B 76, 241–251 (2020)

    Article  CAS  Google Scholar 

  27. C. Balakrishnan, M. Manonmani, M. Santhamoorthy, G. Vinitha, S.P. Meenakshisundaram, J. Mater. Sci: Mater. Electron. 34, 2202 (2023)

    CAS  Google Scholar 

  28. C. Balakrishnan, G. Vinitha, S.P. Meenakshisundaram, J. Mol. Struct. 1253, 132310 (2022)

    Article  CAS  Google Scholar 

  29. C. Balakrishnan, M. Manonmani, S.R. Ahamed, G. Vinitha, S.P. Meenakshisundaram, J. Mol. Struct. 1275, 134569 (2023)

    Article  CAS  Google Scholar 

  30. S. Medhekar, R. Kumar, S. Mukherjee, R.K. Choubey, AIP Conf. Proc. 1512(1), 470–471 (2013)

    Article  CAS  Google Scholar 

  31. S.K. Wolff, D.J. Grim wood, J.J. McKinnon, M.J. Turner, D. Jayatilaka, M.A. Spackman, CrystalExplorer (University of Western Australia, Perth, 2012)

  32. J.D. Dunitz, P. Seiler, Acta Crystallogr. Sect. B Struct. Sci. 30(11), 2739–2741 (1974)

    Article  Google Scholar 

  33. P. Kubelka, F. Munk, Z. Tech. Phys. 12, 593–601 (1931)

    Google Scholar 

  34. N. Sisodia, R. Trivedi, R.K. Choubey, P. Sen, P.K. Sen, S. Kar, K.S. Bartwal, Appl. Phys. A 84, 291–295 (2006)

    Article  CAS  Google Scholar 

  35. W.T. Hsu, Z.B. Chen, C.C. Wu, R.K. Choubey, C.W. Lan, Mater. 5(2), 227–238 (2012)

    Article  CAS  Google Scholar 

  36. J.C. Wu, Z.B. Chen, R.K. Choubey, C.W. Lan, Mater. Chem. Phys. 133(2–3), 813–817 (2012)

    Article  CAS  Google Scholar 

  37. M. Sheik-Bahae, A.A. Said, E.W. Van Stryland, Opt. Lett. 14, 955–957 (1989)

    Article  CAS  PubMed  Google Scholar 

  38. M. Sheik-Bahae, A.A. Said, T.H. Wei, D.J. Hagan, E.W. Van Stryland, IEEE J. Quantum Electron. 26, 760–769 (1990)

    Article  CAS  Google Scholar 

  39. Y. Zhou, E. Wang, J. Peng, J. Liu, C. Hu, R. Huang, X. You, Polyhedron. 18, 1419–1423 (1999)

    Article  CAS  Google Scholar 

  40. L.W. Tutt, T.F. Boggess, Progr Quantum Electron. Progress. 17(4), 299–338 (1993)

    Article  CAS  Google Scholar 

  41. J.C. Johnson, Z. Li, P.F. Ndione, K. Zhu, J. Mater. Chem. C 4(22), 4847–4852 (2016)

    Article  CAS  Google Scholar 

  42. R.W. Boyd, G.L. Fischer, in Encyclopedia of Materials: Science and Technology (Second Edition), 6237–6244 (2001)

  43. Y.G. Gorbunova, A.D. Grishina, A.G. Martynov, T.V. Krivenko, A.A. Isakova, V.V. Savel’ev, S.E. Nefedov, E.V. Abkhalimov, A.V. Vannikov, A.Y. Tsivadze, J. Mater. Chem. C 3(26), 6692–6700 (2015)

    Article  CAS  Google Scholar 

  44. A.V. Vannikov, A.D. Grishina, Y.G. Gorbunova, T.V. Krivenko, A.S. Laryushkin, L.A. Lapkina, V.V. Savelyev, A.Y. Tsivadze, Polym. Sci. Ser. A 53(11), 1069–1075 (2011)

    Article  CAS  Google Scholar 

  45. A.D. Grishina, Y.G. Gorbunova, T.V. Krivenko, L.A. Lapkina, V.V. Savel’ev, A.V. Vannikov, A.Y. Tsivadze, Prot. Met. Phys. Chem. Surf. 50(4), 472–479 (2014)

    Article  CAS  Google Scholar 

  46. S.K. Patra, B.K. Dadhich, B. Bhushan, R.K. Choubey, A. Priyam, ACS Omega. 6(46), 31375–31383 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  47. B.K. Dadhich, I. Kumar, R.K. Choubey, B. Bhushan, A. Priyam, Photochem. Photobiol Sci. 16, 1556–1562 (2017)

    Article  CAS  PubMed  Google Scholar 

  48. M.A. Spackman, J.J. McKinnon, CrystEngComm. 4(66), 378–392 (2002)

    Article  CAS  Google Scholar 

Download references

Funding

The authors thank the Council of Scientific and Industrial Research, New Delhi, for financial support through research grant No. 21 (1024)/16/EMR-II. CB and MM are grateful to the CSIR Emeritus Scientist Scheme for the award of the RA/SRF-ship.

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Authors and Affiliations

  1. Department of Chemistry, Annamalai University, Annamalainagar, Tamil Nadu, Tamil Nadu, 608 002, India

    C. Balakrishnan, M. Manonmani & SP. Meenakshisundaram

  2. Department of Chemistry, Erode Sengunthar Engineering College, Erode, Tamil Nadu, 638057, India

    C. Balakrishnan & P. Suppuraj

  3. KPR Institute of Engineering and Technology, Arasur, Coimbatore, Tamil Nadu, 641407, India

    S. Bhuvaneshwari

  4. Division of Physics, School of Advanced Science, VIT Chennai, Chennai, Tamil Nadu, 600127, India

    G. Vinitha

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Contributions

CB: Conceptualization, Methodology, Investigation, Writing—original draft. MM: Methodology, Investigation, Formal Analysis. PS: Computational Calculations, Formal analysis. SB: Formal analysis. GV: Formal analysis. SPM: Supervision, Conceptualization, Writing—review & editing. All authors read and approved the final manuscript.

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Correspondence to SP. Meenakshisundaram.

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Balakrishnan, C., Manonmani, M., Suppuraj, P. et al. Crystal structure and third-order nonlinear optical properties of supramolecular cocrystals of 18-crown-6 with 5-aminoisophthalic acid. J Mater Sci: Mater Electron 35, 614 (2024). https://doi.org/10.1007/s10854-024-12368-z

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