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Synthesis, crystal growth, spectral, optical, thermal studies on nonlinear optical activity of organic crystal-((E)-(4-fluorophenylimino)methyl)naphthalen-2-ol (E4FMN)

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Abstract

Organic single crystal of ((E)-(4-fluorophenylimino)methyl)naphthalen-2-ol (E4FMN) as efficient NLO material for frequency conversion, optical limiting and optoelectronic applications has been grown within 5 days by using conventional method. From the single crystal X-ray diffraction E4FMN crystallizes in Monoclinic system. FT-IR and NMR data were highly correlated with the single crystal X-ray diffraction structure. Information regarding the thermal stability and melting point were rendered from the TG–DTA thermal studies. The optical analysis (UV–visible) verified that that crystal has very low absorption and cut-off wavelength at 390 nm. The material exhibits green emission in emission spectrum and is suitable for the device fabrication. Z-scan explains the two-photon absorption, reverse saturation absorption of E4FMN is 4.25 × 10−10 m/W and has lower onset limiting threshold value which indicates that it can be used in making laser protection gadgets. The Z-scan method was used to explain the optical limiting qualities of the E4FMN crystal, which had strong third-order non-linear optical properties. The optical behavior of E4FMN is confirmed to be second-order nonlinear using the Kurtz Perry powder approach.

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The datasets generated during the current study are available from the corresponding author on reasonable request.

References

  1. K. Kumar, K. SenthilKannan, R. Hariharasuthan, M. Jothibas, M. Vimalan, P. Baskaran, M. Iyanar, M. Kolanjinathan, Growth of diethyl 3,3′-[(2,4-dichlorophenyl) methylidene]bis(1H-indole-2-carboxylate)-(D32DMBC) organic NLO single crystal and its optical, thermal, mechanical, dielectric and computational studies. J. Mater. Sci.: Mater. Electron. 31, 20816–20823 (2019). https://doi.org/10.1007/s10854-020-04594-y

    Article  CAS  Google Scholar 

  2. C. Vidya, I. Ragavan, A. Arunkumar, P.M. Anbarasan, M. Shkir, Synthesis, crystal structures, spectroscopy, and quantum chemical studies on the 4-dimethylaminopyridinium-2,4-dinitrophenolate: an organic NLO material for optoelectronics. J. Mol. Model. 29(12), 1–16 (2023). https://doi.org/10.1007/s00894-023-05785-0

    Article  CAS  Google Scholar 

  3. K. Xu, Q. Cui, D. Zhong, Z. Yu, T. Wang, L. Cao, Q. Wang, X. Yu, B. Teng, Crystal growth and characterization of 2-(4-(dimethylamino) styryl)-benzothiazole: a potential organic nonlinear optical crystal. Opt. Mater. 111, 110655 (2021). https://doi.org/10.1016/j.optmat.2020.110655

    Article  CAS  Google Scholar 

  4. T. Zhao, C. Wang, S. Hu, S. Ji, C. Hu, K. Xu, B. Teng, Structural design and characterization of a chalcone derivative crystal DAMO with strong SHG efficiency for NLO applications. Opt. Mater. 112, 110765 (2021). https://doi.org/10.1016/j.optmat.2020.110765

    Article  CAS  Google Scholar 

  5. M.L.L. Rose, T. Suthan, S. Goma, Growth and characterization of organic 2,4-dihydroxybenzophenone single crystals for nonlinear optical applications. J. Mater. Sci.: Mater. Electron. 34, 1604 (2023). https://doi.org/10.1007/s10854-023-10933-6

    Article  CAS  Google Scholar 

  6. B. Mohan, M. Choudhary, S. Bharti, A. Jana, N. Das, S. Muhammad, A.G. Al-Sehemi, S. Kumar, Syntheses, characterizations, crystal structures and efficient NLO applications of new organic compounds bearing 2-methoxy-4-nitrobenzeneamine moiety and copper(II) complex of (E)-N′-(3,5-dichloro-2-hydroxybenzylidene) benzohydrazide. J. Mol. Struct. 1190, 54–67 (2019). https://doi.org/10.1016/j.molstruc.2019.04.059

    Article  CAS  ADS  Google Scholar 

  7. E. Priyadharshini, P. Vinothkumar, P. Jayaprakash, Crystal growth and physico-chemical characterization of an organic 2-amino-6-methyl pyridinium L-tartrate single crystal for optoelectronic device applications. J. Mater. Sci.: Mater. Electron. 34, 245 (2023). https://doi.org/10.1007/s10854-022-09750-0

    Article  CAS  Google Scholar 

  8. P. Karuppasamy, T. Kamalesh, K. Anitha, M.S. Pandian, P. Ramasamy, S. Verma, Design and growth of novel organic molecular quinoline 4-nitrophenol (QNP) single crystals: for nonlinear optical (NLO) applications. J. Mol. Struct. 1210, 128036 (2020). https://doi.org/10.1016/j.molstruc.2020.128036

    Article  CAS  Google Scholar 

  9. T. Pei, L. Zhou, Q. Zhang, D. Ma, Y. Bai, Q. Yin, C. Xie, Studies on structure, NLO properties of a new organic NLO crystal: guanidinium 3,5-dihydroxybenzoate. J. Mater. Sci.: Mater. Electron. 30, 2994–3003 (2019). https://doi.org/10.1007/s10854-018-00578-1

    Article  CAS  Google Scholar 

  10. S. Ramkumar, R. Rajalakshmi, Synthesis, spectral, single crystal XRD structure, Hirshfeld surface, molecular docking and in silico ADMET studies of symmetrical azine: 1,2-bis(4(methylthio)benzylidene)hydrazine. Mater. Today Proc. (2023). https://doi.org/10.1016/j.matpr.2023.05.63

    Article  Google Scholar 

  11. S. Boomadevi, M. Venkatesh, P. Gayathri, S.P. Anthony, A.K. Chaudhary, K. Pandiyan, D. Sastikumar, Growth and THz generation in organic nonlinear optical crystal: N,N′ bis(4-nitrophenyl)(1R,2R)-diaminocyclohexane (BNDC). J. Mater. Sci.: Mater. Electron. 31, 13628–13635 (2020). https://doi.org/10.1007/s10854-020-03919-1

    Article  CAS  Google Scholar 

  12. S. Mugeshini, R. Santhakumari, N. Rajeswari, G. Amudha, D. Chandrika, S. Sagadevan, Growth and computational studies on vanillin isoniazid single crystals. Chin. J. Phys. 72, 229–239 (2021). https://doi.org/10.1016/j.cjph.2021.04.025

    Article  CAS  Google Scholar 

  13. R. Subramaniyan, R. Ramarajan, A. Ramalingam, S. Sambandam, A. Petersamy, A.R. Guerroudj, N. Boukabcha, A. Chouaih, Microwave assisted synthesis, vibrational spectra, Hirshfeld surface and interaction energy, DFT, topology, in silico ADMET and molecular docking studies of 1,2-bis(4-methoxybenzylidene)hydrazine. J. Mol. Struct. 1278, 134946 (2023). https://doi.org/10.1016/j.molstruc.2023.134946

    Article  CAS  Google Scholar 

  14. S. Ramkumar, R. Ramarajan, Green synthesis, single-crystal X-RD, Hirshfeld analysis and anti-covid-19 molecular docking investigation of symmetrical azines. ChemistrySelect (2023). https://doi.org/10.1002/slct.202204494

    Article  Google Scholar 

  15. M. Rajkumar, J. Maalmarugan, G. Flora, S. Surendarnath, S. Christy, P. Periyathambi, S. Kumar, Growth, characterizations, and the structural elucidation of diethyl-2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene) malonate crystalline specimen for dielectric and electronic filters, thermal, optical, mechanical, and biomedical applications using conventional experimental and theoretical practices. J. Mater. Sci.: Mater. Electron. 32(18), 22822–22839 (2021). https://doi.org/10.1007/s10854-021-06761-1

    Article  CAS  Google Scholar 

  16. S. Surya, B. Gunasekaran, T.S. Girisun, Synthesis, growth, crystal structure, thermal, optical, electrical and third-order nonlinear optical properties of creatininium phthalate as a new nonlinear optical single crystal. J. Mater. Sci.: Mater. Electron. 33(11), 8683–8701 (2022). https://doi.org/10.1007/s10854-021-06771-z

    Article  CAS  Google Scholar 

  17. P. Justin, K. Anitha, M.B. Ahamed, Enhanced piezoelectric, optical, mechanical, and laser damage threshold studies on creatinine doped glycine single crystals. J. Mater. Sci.: Mater. Electron. 30, 9735–9741 (2019). https://doi.org/10.1007/s10854-019-01308-x

    Article  CAS  Google Scholar 

  18. V. Crasta, V. Ravindrachary, R.F. Bhajantri, R. Gonsalves, Growth and characterization of an organic NLO crystal: 1-(4-methylphenyl)-3-(4-methoxyphenyl)-2-propen-1-one. J. Cryst. Growth 267(1–2), 129–133 (2004). https://doi.org/10.1016/j.jcrysgro.2004.03.037

    Article  CAS  ADS  Google Scholar 

  19. T. Murugan, S. Suresh, B.M. Boaz, Studies on the growth and characterization of a new organic nonlinear optical single crystal: 2-amino 5-methyl-pyridinium 4-methoxybenzoate for optoelectronic and photonic devices. Opt. Mater. 136, 113379 (2023). https://doi.org/10.1016/j.optmat.2022.113379

    Article  CAS  Google Scholar 

  20. K. Ramachandran, A. Raja, V. Mohankumar, M.S. Pandian, P. Ramasamy, Experimental and theoretical approach of organic 4,4′-dimethylbenzophenone (DMBP) single crystal for NLO application. Opt. Laser Technol. 119, 105640 (2019). https://doi.org/10.1016/j.optlastec.2019.105640

    Article  CAS  Google Scholar 

  21. L.R. Keerthi, S. Anand, S. Kalainathan, D. Jaikumar, Investigation on the growth, optical, electrical, thermal and third order NLO properties of 2-(4-methlybenzylidene) malononitrile (MBM) single crystal. Opt. Mater. 109, 110216 (2020). https://doi.org/10.1016/j.optmat.2020.110216

    Article  CAS  Google Scholar 

  22. R.P. Jebin, T. Suthan, T.R. Anitha, N.P. Rajesh, G. Vinitha, Growth and characterization of organic material 3,4-dimethoxybenzaldehyde-2,4-dinitroaniline single crystal. J. Mater. Sci.: Mater. Electron. 32, 3232–3246 (2021). https://doi.org/10.1007/s10854-020-05072-1

    Article  CAS  Google Scholar 

  23. R. Kaliammal, S. Sudhahar, G. Parvathy, K. Velsankar, K. Sankaranarayanan, Physicochemical and DFT studies on new organic bis-(2-amino-6-methylpyridinium) succinate monohydrate good quality single crystal for nonlinear optical applications. J. Mol. Struct. 1212, 128069 (2020). https://doi.org/10.1016/j.molstruc.2020.128069

    Article  CAS  Google Scholar 

  24. S. Prince, T. Suthan, C. Gnanasambandam, N.P. Rajesh, G. Vinitha, Growth and characterization of organic 4-methyl-2-nitroaniline single crystals for nonlinear optical applications. J. Mater. Sci.: Mater. Electron. 33(8), 5909–5923 (2022). https://doi.org/10.1007/s10854-022-07772-2

    Article  CAS  Google Scholar 

  25. S. Sathiya, M. Senthilkumar, P. Umarani, Synthesis, structural, spectroscopical and DFT studies on third order NLO crystal: ethyl-5-hydroxy-4-(2-hydroxyphenyl)-2-oxo-6-(trifluoromethyl) hexahydropyrimidine5-carboxylate (EHOTHPC). J. Mol. Struct. 1224, 129017 (2021). https://doi.org/10.1016/j.molstruc.2020.129017

    Article  CAS  Google Scholar 

  26. S. Nandhini, P. Murugakoothan, Synthesis, growth, optical, thermal, electrical and third-order nonlinear properties of an organic single crystal guanidinium 3,5 dinitrosalicylate: a promising candidate for nonlinear optical applications. Opt. Mater. 113, 110714 (2021). https://doi.org/10.1016/j.optmat.2020.110714

    Article  CAS  Google Scholar 

  27. J. Maalmarugan, V. Yokeswaran, R. Divya, H. Ganesan, R.P. Patel, G. Flora, K. SenthilKannan, Synthesis, growth, XRD, NLO, CHNSO, structure by theoretical approach, dielectric, absorbance, photoconductivity and bio studies of 4-(4-acetyl-5-methyl-1h-1,2,3-triazol-1-yl) benzonitrile crystals for optical, opto-electronic, and photonics utilities. J. Mater. Sci.: Mater. Electron. 32, 13850–13858 (2021). https://doi.org/10.1007/s10854-021-05960-0

    Article  CAS  Google Scholar 

  28. K.S. Ramesh, M. Saravanabhavan, M. Rajkumar, D. Edison, M. Sekar, S. Muhammad, A.G. Al-Sehemi, Synthesis, growth, structural, thermal, third order nonlinear and computational studies of organic single crystal: 2-amino-4-picolinium 2-chloro-4-nitrobenzoate. Opt. Mater. 96, 109341 (2019). https://doi.org/10.1016/j.optmat.2019.109341

    Article  CAS  Google Scholar 

  29. S. Vediyappan, A. Raja, R.M. Jauhar, R. Kasthuri, V. Vijayan, M.S. Pandian, R. Perumalsamy, V. Gandhiraj, Synthesis, crystal growth, structure, crystalline perfection, thermal, linear, and nonlinear optical investigations on 2-amino-5-nitropyridine 4-chlorobenzoic acid (1:1): a novel organic single crystal for NLO and optical limiting applications. J. Mater. Sci.: Mater. Electron. 32(11), 15026–15045 (2021). https://doi.org/10.1007/s10854-021-06056-5

    Article  CAS  Google Scholar 

  30. S. Nandhini, P. Murugakoothan, Growth and characterization of a novel organic nonlinear optical crystal guanidinium 4-hydroxybenzoate: potential candidate for opto-electronic applications. Mater. Lett. 241, 152–155 (2019). https://doi.org/10.1016/j.matlet.2019.01.067

    Article  CAS  Google Scholar 

  31. K. Nivetha, K. Aravinth, K. Senthil, S. Kalainathan, Evaluation of structural, spectral, thermal and optical properties of an efficient centrosymmetric organic single crystal 2-[2-(4-diethylamino-phenyl)-vinyl]-1-methyl pyridinium tetrafluoroborate for nonlinear optical applications. J. Mol. Struct. 1225, 129082 (2021). https://doi.org/10.1016/j.molstruc.2020.129082

    Article  CAS  Google Scholar 

  32. V. Siva, S.A. Bahadur, A. Shameem, S. Athimoolam, K.U. Lakshmi, G. Vinitha, Synthesis, structural, vibrational, thermal, dielectric and optical properties of third order nonlinear optical single crystal for optical power limiting applications. J. Mol. Struct. 1191, 110–117 (2019). https://doi.org/10.1016/j.molstruc.2019.04.091

    Article  CAS  ADS  Google Scholar 

  33. K. Kumar, V.C. Vincent, G. Bakiyaraj, K. Kirubavathi, K. Selvaraju, Investigations of solid state, optical, NLO, dielectric and mechanical behavior of methyl para-hydroxybenzoate crystal. Optik 226, 165738 (2021). https://doi.org/10.1016/j.ijleo.2020.165738

    Article  CAS  ADS  Google Scholar 

  34. S. Karthick, K. Thirupugalmani, M. Krishnakumar, V. Kannan, G. Vinitha, S. Brahadeeswaran, Synthesis, structural, dielectric, laser damage threshold, third order nonlinear optical and quantum chemical investigations on a novel organic crystalline material: pyrrolidin-1-ium 2-chloro-4-nitrobenzoate 2-chloro-4-nitrobenzoic acid for opto-electronic applications. Opt. Laser Technol. 122, 105849 (2020). https://doi.org/10.1016/j.optlastec.2019.105849

    Article  CAS  Google Scholar 

  35. A.U. Habeeba, M. Saravanan, T.S. Girisun, S. Anandan, Nonlinear optical studies of conjugated organic dyes for optical limiting applications. J. Mol. Struct. 1240, 130559 (2021). https://doi.org/10.1016/j.molstruc.2021.130559

    Article  CAS  Google Scholar 

  36. P. Jaikumar, T. Balakrishnan, K. Ramamurthi, M. Saravanan, T.C. Sabari Girisun, Synthesis, growth, and two-photon absorption induced optical limiting action of cytosinium benzoate single crystal. J. Mater.: Sci. Mater. 33(22), 17502–17512 (2022). https://doi.org/10.1007/s10854-022-08607-w

    Article  CAS  Google Scholar 

  37. P. Reena, S.E. Joema, B. Gunasekaran, S. Sindhusha, T.S. Girisun, D.A. Darling, Scrutinizing the optical limiting action of a novel carbonyl guanidinium hippurate for laser safety device applications. Opt. Mater. 132, 112749 (2022). https://doi.org/10.1016/j.optmat.2022.112749

    Article  CAS  Google Scholar 

  38. M. Neela, B. Premalatha, P. Punitha, T.S. Girisun, Synthesis, structural, third-order nonlinear optical properties and hirshfeld surface analysis of 1-((E)-(4-chlorophenylimino) methyl) naphthalen-2-ol. Optik 290, 171302 (2023). https://doi.org/10.1016/j.ijleo.2023.171302

    Article  CAS  ADS  Google Scholar 

  39. M. Neela, B. Premalatha, P. Punitha, T.C. Sabari Girisun, Crystal growth, spectral, optical, thermal and nonlinear optical activity of organic crystal 1-((E)-(2,5-dichlorophenylimino) methyl) naphthalen-2-ol (E25DCM). J. Mater. Sci.: Mater. Electron. 34(30), 2008 (2023). https://doi.org/10.1007/s10854-023-11383-w

    Article  CAS  Google Scholar 

  40. K. Krishnaraj, P. Praveen Kumar, Crystal growth, optical, thermal, dielectric and mechanical studies on a nonlinear organic optical material: guanidinium fumarate dihydrate (GFDH) single crystal. J. Mater. Sci. Mater. Electron. 31, 22131–22142 (2020). https://doi.org/10.1007/s10854-020-04715-7

    Article  CAS  Google Scholar 

  41. A. Alexandar, I. Johnson, A.M. Dayana, T.S. Girisun, B.S.I. Lasalle, M.S. Pandian, Investigations on growth, XRD, strain, FTIR, UV–Vis NIR, photoluminescence, SHG, and Z-scan analyses of L-cysteine picrate single crystal for NLO and optical limiting applications. Inorg. Chem. Commun. (2023). https://doi.org/10.1016/j.inoche.2023.111751

    Article  Google Scholar 

  42. S. Shalini, S.S. Kirupavathy, E. Jerusha, Growth and characterisation of dimethylamino pyridinium p-bromo-chlorophenolate mixed crystal: a new organic NLO material for terahertz applications. J. Mol. Struct. 1178, 126–134 (2019). https://doi.org/10.1016/j.molstruc.2018.10.020

    Article  CAS  ADS  Google Scholar 

  43. S. Sathiya, M. Senthilkumar, Study on the synthesis, structural, spectroscopic, thermal, DFT and NLO property of ethyl 4-hydroxy-2-oxo-6-(thiophen-3-yl)-4-(trifluoromethyl) hexahydropyrimidine-5-carboxylate (EHTHPC). J. Mol. Struct. 1203, 127213 (2020). https://doi.org/10.1016/j.molstruc.2019.127213

    Article  CAS  Google Scholar 

  44. G. Parvathy, R. Kaliammal, G. Maheshwaran, P. Devendran, M.K. Kumar, S. Sudhahar, Experimental and theoretical studies on 4-hydroxy-3-methoxybenzaldehyde nicotinamide organic co-crystal for third harmonic nonlinear optical applications. J. Mater. Sci.: Mater. Electron. 31, 18937–18953 (2020). https://doi.org/10.1007/s10854-020-04431-2

    Article  CAS  Google Scholar 

  45. R. Chen, K. Xu, G. Wang, Z. Zhang, L. Cao, B. Teng, Theoretical and experimental investigation of a pyridinium-based NLO crystal 4-N,N-dimethylamino-4′-N′-methyl-stilbazolium 3,4-dimethoxysulfonate. Optik 257, 168830 (2022). https://doi.org/10.1016/j.ijleo.2022.168830

    Article  CAS  ADS  Google Scholar 

  46. R. Sathishkumar, K. SenthilKannan, C.J. Magesh, K. Venkatapathy, M. Vimalan, D. Sankar, S. Tamilselvan, Synthesis, growth and characterization of 2,5-dimethyl-N-(3-phenylprop-2-en-1-ylidene) aniline (2,5 DPPA) single crystal: a new second order nonlinear optical material for photonic and optoelectronic applications. Optik 226, 165947 (2021). https://doi.org/10.1016/j.ijleo.2020.165947

    Article  CAS  ADS  Google Scholar 

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Acknowledgements

The authors would like to express their gratitude to the DST PURSE Phase II, Department of Chemistry, Annamalai university for NMR analysis, and convey thanks to Single Crystal XRD Facility- VIT, Vellore. The facilities provided by the BS Abdur Rahman University (BSAU)-Chennai, St. Joseph’s College, Trichy are gratefully acknowledged.

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Authors and Affiliations

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

    M. Neela, B. Premalatha & P. Punitha

  2. PG & Research Department of Chemistry, Government Arts College, Chidambaram, Tamil Nadu, 608 102, India

    B. Premalatha

  3. Department of Chemistry, Srinivasa Subbaraya Polytechnic College, Puthur, Mayiladuthurai, Tamil Nadu, 609 108, India

    P. Punitha

  4. Nano Photonics Laboratory, School of Physics, Bharathidasan University, Tiruchirappalli, Tamil Nadu, 620 024, India

    T. C. Sabari Girisun

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MN: investigation, conceptualization, writing original draft, formal analysis, data curation, software. BP: investigation, conceptualization, resources, supervision, editing, methodology, formal analysis. PP: conceptualization, supervision, methodology, formal analysis. TCSG: formal analysis.

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Neela, M., Premalatha, B., Punitha, P. et al. Synthesis, crystal growth, spectral, optical, thermal studies on nonlinear optical activity of organic crystal-((E)-(4-fluorophenylimino)methyl)naphthalen-2-ol (E4FMN). J Mater Sci: Mater Electron 35, 372 (2024). https://doi.org/10.1007/s10854-024-12119-0

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