Charge–transfer architecture and intermolecular interaction landscape in 1H-benzotriazol-3-ium perchlorate hydrate: structural, optical, surface, and third-order optical response analysis

1. R.W. Boyd, A.L. Gaeta, E. Giese, Nonlinear Optics, in Springer Handbook of Atomic, Molecular, and Optical Physics, Springer Handbooks. ed. by G.W.F. Drake (Springer, Cham, 2023)

2. Y.R. Shen, The Principles of Nonlinear Optics (John Wiley & Sons, New York, 1984)

3. P.A. Franken, A.E. Hill, C.W. Peters, G. Weinreich, Generation of optical harmonics. Phys. Rev. Lett. 7(4), 118 (1961). https://doi.org/10.1103/PhysRevLett.7.11810.1103/PhysRevLett.7.118 ↗

4. J. Zyss, I. Ledoux, Nonlinear optics in multipolar media: theory and experiments. Chem. Rev. 94(1), 77–105 (1994). https://doi.org/10.1021/cr00025a00310.1021/cr00025a003 ↗

5. P.N. Prasad, D.J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, vol. Vol. 1 (John Wiley & Sons, New York, 1991)

6. D.S. Chemla (ed.), Nonlinear Optical Properties of Organic Molecules and Crystals, vol. Vol. 1 (Elsevier, 2012)

7. R. Masse, J.F. Nicoud, R.J. Twieg, Nonlinear optical properties of organic materials and crystals. Chem. Rev. 92, 113–126 (1992). https://doi.org/10.1021/cr00011a00510.1021/cr00011a005 ↗

8. A. Arumugam, M. Sekar, R. Shanmugam, S.K. Lakkaboyana, P. Seepana, M. Iqbal, Exploring crystal structure, spectral, optical, and nonlinear optical properties of hydrazide-type Schiff base through integrated experimental and computational approach. J. Mater. Sci. Mater. Electron. 36, 1237 (2025). https://doi.org/10.1007/s10854-025-15335-410.1007/s10854-025-15335-4 ↗

9. F. Ebenazer, S. Munusamy, S. Sampathkumar, R. Shanmugam, S. Muhammad, A.R. Chaudhry, S.K. Lakkaboyana, H. Trilaksana, R.M.N. Kalla, J. Lee, P. Seepana, Synthesis, spectral, crystal structure, linear and NLO properties of quinoline Schiff base: combined experimental and DFT calculations. J. Mol. Struct. 1324, 140781 (2025). https://doi.org/10.1016/j.molstruc.2024.14078110.1016/j.molstruc.2024.140781 ↗

10. K.S. Ramesh, S. Munusamy, M. Saravanakumar, M. Sekar, K. Muthusamy, M. Kumar, G. Vinitha, Exploring the structural and optical characteristics of the charge transfer complex 2,3-dimethylquinoxaliniumpicrate: a comprehensive investigation through experimental and computational approaches. J. Mater. Sci. Mater. Electron. 35, 1314 (2024). https://doi.org/10.1007/s10854-024-12989-410.1007/s10854-024-12989-4 ↗

11. S. Munusamy, K.R. Aranganayagam, C. Sivasankari, K.S. Ramesh, Exploring the nonlinear optical properties of 6-ethoxy-2-aminobenzothiazolium-4-methoxyphenyl acetate: experimental and computational insights into a monoclinic single crystal. Opt. Mater. 152, 115497 (2024). https://doi.org/10.1016/j.optmat.2024.11549710.1016/j.optmat.2024.115497 ↗

12. M. Fleck, L. Bohatý, Benzotriazole and its protonated forms: structural features and hydrogen bonding. Acta Crystallogr. C 61, o389–o391 (2005). https://doi.org/10.1107/S010827010501718610.1107/S0108270105017186 ↗

13. D. Xu, D. Xue, Chemical bonding and nonlinear optical properties of inorganic crystals. J. Phys. Chem. B 110, 1421–1425 (2006). https://doi.org/10.1021/jp054366u10.1021/jp054366u ↗

14. M.H. Jiang, Q. Fang, Organic and semiorganic nonlinear optical materials. Adv. Mater. 11, 1147–1151 (1999). https://doi.org/10.1002/(SICI)1521-4095(199909)11:13%3c1147::AID-ADMA1147%3e3.0.CO;2-H10.1002/(SICI)1521-4095(199909)11:13<1147::AID-ADMA1147>3.0.CO;2-H ↗

15. K.E. Babu, K. Ramamurthi, G. Bhagavannarayana, Synthesis, growth and properties of a novel organic nonlinear optical material: benzimidazolium perchlorate. Opt. Laser Technol. 45, 527–532 (2013). https://doi.org/10.1016/j.optlastec.2012.06.00210.1016/j.optlastec.2012.06.002 ↗

16. M. Sheik‑Bahae, A.A. Said, T.‑H. Wei, D.J. Hagan, E.W. Van Stryland, Sensitive measurement of optical nonlinearities using a single beam. IEEE J. Quantum Electron. 26, 760–769 (1990). https://doi.org/10.1109/3.5339410.1109/3.53394 ↗

17. S.K. Wolff, D.J. Grimwood, J.J. McKinnon, M.J. Turner, D. Jayatilaka, M.A. Spackman, CrystalExplorer (Version 3.1), University of Western Australia, Crawley, WA, 2012; see also M.A. Spackman, J.J. McKinnon, CrystEngComm 4: 378–384.

18. A. Frisch, H.P. Hratchian, R.D. Dennington II, T.A. Keith, J. Millam, A.B. Nielsen, A.J. Holder, J. Hiscocks, GaussView 5.0.8, Gaussian Inc., Wallingford CT, 2009.

19. G.M. Sheldrick, Crystal structure refinement with SHELXL. Acta Crystallogr. C Struct. Chem. 71, 3–8 (2015). https://doi.org/10.1107/S205322961402421810.1107/S2053229614024218 ↗

20. D. Lee, H. Bu, D. Kim, J. Hyoung, S.T. Hong, Crystal structure of calcium perchlorate anhydrate, Ca(ClO4)2, from laboratory powder X-ray diffraction data. Acta Crystallogr. Sect. E Crystallogr. Commun. 74, 514–517 (2018). https://doi.org/10.1107/S205698901800732X10.1107/S205698901800732X ↗

21. B. Ravindran Durai Nayagam, S.R. Jebas, C. Daisy, D. Schollmeyer, 1,1′-[2,3,5,6-Tetramethyl-p-phenylenebis(methyleneoxy)]di-1H-benzotriazole. Acta Crystallogr. Sect. E Struct. Rep. Online 65, o918 (2009). https://doi.org/10.1107/S160053680901078210.1107/S1600536809010782 ↗

22. R.K. Belter, F.R. Fronczek, Bis(1,2,3-benzotriazolium) sulfate dihydrate. Acta Crystallogr. Sect. E Struct. Rep. Online 69, o606–o607 (2013). https://doi.org/10.1107/S160053681300747210.1107/S1600536813007472 ↗

23. R.M. Silverstein, G.C. Bassler, T.C. Morrill, Spectrometric Identification of Organic Compounds, 7th ed. (Wiley, 2005)

24. K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry, 6th ed. (John Wiley & Sons, Hoboken, NJ, 2009). https://doi.org/10.1002/978047040588810.1002/9780470405888 ↗

25. H. Zollinger, Color Chemistry: Syntheses, Properties and Applications of Organic Dyes and Pigments, 3rd ed. (Wiley-VCH, Weinheim, 2003). https://doi.org/10.1002/352760201110.1002/3527602011 ↗

26. D.A. Skoog, F.J. Holler, T.A. Nieman, Principles of Instrumental Analysis (Saunders College Publishing, 1980)

27. J.I. Pankove, Optical Processes in Semiconductors (Courier Corporation, 2012)

28. M. Shellaiah, K.W. Sun, Benzotriazole-based π-conjugated systems: synthesis, photophysical and optoelectronic properties. J. Photochem. Photobiol. C 31, 1–20 (2017). https://doi.org/10.1016/j.jphotochemrev.2017.02.00110.1016/j.jphotochemrev.2017.02.001 ↗

29. P. Kubelka, Ein Beitrag zur Optik der Farbanstriche. Z. Tech. Phys. 12, 593–601 (1931)

30. J. Tauc, Optical properties and electronic structure of amorphous Ge and Si. Mater. Res. Bull. 3, 37–46 (1968). https://doi.org/10.1016/0025-5408(68)90023-810.1016/0025-5408(68)90023-8 ↗

31. J. Tauc, R. Grigorovici, A. Vancu, Optical properties and electronic structure of amorphous germanium. Phys. Status Solidi 15, 627–637 (1966). https://doi.org/10.1002/pssb.1966015022410.1002/pssb.19660150224 ↗

32. S. Radhakrishnan, B. Krishnakumar, Growth, structural, optical and luminescence properties of organic benzotriazole single crystals. J. Mol. Struct. 1108, 1–8 (2016). https://doi.org/10.1016/j.molstruc.2015.11.06410.1016/j.molstruc.2015.11.064 ↗

33. A. Arunkumar, P. Ramasamy, Studies on the structure, growth and characterization of morpholinium perchlorate single crystals. J. Cryst. Growth 388, 124–131 (2014). https://doi.org/10.1016/j.jcrysgro.2013.10.00510.1016/j.jcrysgro.2013.10.005 ↗

34. S. Manikandan, P. Krishnan, P. Rajesh, T. Sundareswaran, Synthesis, growth, structural, and optical properties of benzotriazolium oxalate dihydrate (BTO) single crystal. J. Mater. Sci. Mater. Electron. 34, 1855 (2023). https://doi.org/10.1007/s10854-023-11240-w10.1007/s10854-023-11240-w ↗

35. J.J. McKinnon, M.A. Spackman, A.S. Mitchell, Novel tools for visualizing and exploring intermolecular interactions in molecular crystals. Acta Crystallogr. B 60(6), 627–668 (2004). https://doi.org/10.1107/S010876810402030010.1107/S0108768104020300 ↗

36. K. Fukui, Role of frontier orbitals in chemical reactions. Science 218, 747–754 (1982). https://doi.org/10.1126/science.218.4574.747210.1126/science.218.4574.7472 ↗

37. R.G. Parr, R.G. Pearson, Absolute hardness: companion parameter to absolute electronegativity. J. Am. Chem. Soc. 105, 7512–7516 (1983). https://doi.org/10.1021/ja00364a00510.1021/ja00364a005 ↗

38. R.G. Parr, L.V. Szentpály, S. Liu, Electrophilicity index. J. Am. Chem. Soc. 121, 1922–1924 (1999). https://doi.org/10.1021/ja983494x10.1021/ja983494x ↗

39. A. Waheed, S. Muhammad, M.A. Gilani, M. Adnan, Z. Aloui, A systematic and comparative analysis of four major classes of DFT functionals to compute linear and nonlinear optical properties of benchmark molecules. J. Comput. Biophys. Chem. 20(5), 517–528 (2021). https://doi.org/10.1142/S273741652150030710.1142/S2737416521500307 ↗

40. C.H. Suresh, G.S. Remya, P.K. Anjalikrishna, Molecular electrostatic potential analysis: a powerful tool to interpret and predict chemical reactivity. WIREs Comput. Mol. Sci. 12, e1601 (2022). https://doi.org/10.1002/wcms.160110.1002/wcms.1601 ↗

41. R.W. Boyd, Nonlinear Optics, 3rd edn. (Academic Press, Burlington, 2008)

42. D.L.M. Cordova, K. Chua et al., Anisotropy-driven crystallization of dimensionally resolved quasi-1D van der Waals nanostructures. J. Am. Chem. Soc. 145(41), 22413–22424 (2023). https://doi.org/10.1021/jacs.3c0588710.1021/jacs.3c05887 ↗

43. G. New, Introduction to Nonlinear Optics (Cambridge University Press, Cambridge, 2011), pp.76–115. https://doi.org/10.1017/CBO978051197585110.1017/CBO9780511975851 ↗

44. M. Saravanan, T.C. Sabari Girisun, G. Vinitha, S. Venugopal Rao, Improved third-order optical nonlinearity and optical limiting behaviour of (nanospindle and nanosphere) zinc ferrite decorated reduced graphene oxide under continuous and ultrafast laser excitation. RSC Adv. 6, 91083–91092 (2016). https://doi.org/10.1039/C6RA18843A10.1039/C6RA18843A ↗

45. C. Yogeswari, T.C.S. Girisun, R. Nagalakshmi, Electrospun 2-nitroaniline (2NA)–poly(methyl methacrylate) (PMMA) nanofibers for power limiting and Q-switching applications. Chem. Phys. Lett. 786, 139209 (2022). https://doi.org/10.1016/j.cplett.2021.13920910.1016/j.cplett.2021.139209 ↗

46. B. Lasalle, B. Sahaya Infant, M.S. Pandian, K. Anitha, P. Ramasamy, Single crystal growth of 1,2,3-Benzotriazole 3,5-dinitrobenzoic acid (BTNBA) by slow evaporation solution technique (SEST) for nonlinear optical (NLO) applications. Inorg. Chem. Commun. 162, 112190 (2024). https://doi.org/10.1016/j.inoche.2024.11219010.1016/j.inoche.2024.112190 ↗

47. T. Sundareswaran, S. Manikandan, P. Rajesh, B.M. Boaz, Growth, elemental, spectral, linear photoconductivity, dielectric, thermal, and Z-scan analysis of benzotriazolium oxalate dihydrate single crystal for third-order harmonic generation applications. J. Mater. Sci. Mater. Electron. 36(1), 27 (2025). https://doi.org/10.1007/s10854-024-14053-710.1007/s10854-024-14053-7 ↗

48. K.Y. Chen, H.S. Wang, S.P. Su, S.W. Kuo, C.K. Lee, A.F.M. El-Mahdy, Π‐electron‐extended porphyrin‐linked covalent organic framework for a Q‐switched all‐solid‐state laser. Adv. Photonics Res. 4(1), 2200145 (2023). https://doi.org/10.1002/adpr.20220014510.1002/adpr.202200145 ↗