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Studies on growth and characterization of (E)-N′-[4-(dimethylamino) benzylidene]-4-hydroxybenzohydrazide hemihydrate: a nonlinear optical material

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Abstract

Hydrazone compound (E)-N′-[4-(dimethylamino) benzylidene]-4-hydroxybenzohydrazide hemihydrate (DMABHBH) was synthesized and single crystals of DMABHBH were grown by solvent evaporation method at room temperature. Molecular structure of DMABHBH compound was confirmed by 1H and 13C nuclear magnetic resonance techniques. The presence of functional groups was confirmed by Fourier transform infrared and FT Raman spectral analyses. The X-ray crystal structure was elucidated at 173 K by single crystal X-ray diffraction and the results were compared with the corresponding values obtained at 298 K. The compound crystallizes in the chiral monoclinic space group P21. Mechanical stability of the grown crystals was estimated from the Vicker’s microhardness test. Powder second harmonic generation efficiency of DMABHBH is about 1.1 times that of potassium dihydrogen phosphate. DMABHBH is found to show optical limiting behavior at high input light intensities, the third order nonlinear optical absorption coefficient measured using open aperture Z-scan studies, is 0.95 × 10−11 m/W. Anti-bacterial activity was studied using the well and disc diffusion methods.

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References

  1. Y.P. Kitaev, B.I. Buzykin, T.V. Troepolskaya, Russ. Chem. Rev. 39, 441–456 (1970)

    Article  Google Scholar 

  2. C. Serbutoviez, C. Bosshard, G. Knopfle, P. Wyss, P. Petre, P. Gunter, K. Schenk, E. Solari, G. Chapuis, Chem. Mater. 7, 1198–1206 (1995)

    Article  Google Scholar 

  3. Z.-Y. Zhou, Y. Li, D.-S. Ding, W. Zhang, S. Shi, B.-S. Shi, G.-C. Guo, Opt. Express 22, 23673–23678 (2014)

    Article  Google Scholar 

  4. S. Ast, R.M. Nia, A. Schonbeck, N. Lastzka, J. Steinlechner, T. Eberle, M. Mehmet, S. Steinlechner, R. Schnabel, Opt. Lett. 36, 3467–3469 (2011)

    Article  Google Scholar 

  5. F. Steinlechner, N. Hermosa, V. Pruneri, J.P. Torres, Nat. Sci. Rep. 6, 21390 (2016)

    Article  Google Scholar 

  6. A. Auger, W.J. Blau, P.M. Burnham, I. Chambrier, M.J. Cook, B. Isare, F. Nekelson, S.M.O. Flaherty, J. Mater. Chem. 13, 1042–1047 (2003)

    Article  Google Scholar 

  7. V.M. Naik, M.I. Sambrani, M.B. Mallur, Indian J. Chem. 47, 1793–1797 (2008)

    Google Scholar 

  8. K.K. Narang, V.P. Singh, Synth. React. Inorg. Met. Org. Chem. 27, 721–729 (1997)

    Article  Google Scholar 

  9. C. Loncle, J.M. Brunel, N. Vidal, M. Dherbomez, Y. Letourneux, Eur. J. Med. Chem. 39, 1067–1071 (2004)

    Article  Google Scholar 

  10. R. Todeschini, A.L.P. de Miranda, K.C.M. da Silva, S.C. Parrini, E.J. Barreiro, Eur. J. Med. Chem. 33, 189–199 (1998)

    Article  Google Scholar 

  11. S.G. Kucukguzel, A. Mazi, F. Sahin, S. Ozturk, J.P. Stables, Eur. J. Med. Chem. 38, 1005–1013 (2003)

    Article  Google Scholar 

  12. P. Melnyk, V. Leroux, C. Sergheraert, P. Grellier, C. Sergheraert, Bioorg. Med. Chem. Lett. 16, 31–35 (2006)

    Article  Google Scholar 

  13. P.C. Lima, L.M. Lima, K.C.M. da Silva, P.H.O. Le da, A.L.P. de Miranda, C.A.M. Fraga, E.J. Barreiro, Eur. J. Med. Chem. 35, 187–203 (2000)

    Article  Google Scholar 

  14. C. Cunha, J.M. Figueiredo, J.L.M. Tributino, A.L.P. Miranda, H.C. Castro, R.B. Zingali, C.A.M. Fraga, M.C.B.V. de Souza, V.F. Ferreira, E.J. Barreiro, Bioorg. Med. Chem. 11, 2051–2059 (2003)

    Article  Google Scholar 

  15. K.K. Bedia, O. Elc, U. Seda, K. Fatma, S. Nathaly, R. Sevim, A. Dimoglo, Eur. J. Med. Chem. 41, 1253–1261 (2006)

    Article  Google Scholar 

  16. N. Terzioglu, A. Gursoy, Eur. J. Med. Chem. 38, 781–786 (2003)

    Article  Google Scholar 

  17. M. Katyal, G. Dutt, Talanta, 22 (1975) 151–166

    Article  Google Scholar 

  18. A. Galiano-Roth, D.B. Collum, J. Am. Chem. Soc. 110, 3546–3553 (1988)

    Article  Google Scholar 

  19. Z. Xia, L.W. Hu, X. Wang, Bioorg. Med. Chem. 17, 3374–3377 (2007)

    Google Scholar 

  20. R. Vijaya, B. Narayana, B. Ashalatha, B.K. Sarojani, Eur. J. Med. Chem. 42, 425–429 (2007)

    Article  Google Scholar 

  21. A. Badi, H. Eissa, A.A. Husain, Chem. Pharm. Bull. 51, 833–847 (2003)

    Google Scholar 

  22. B.G. Bonde, N.J. Gaikwad, Biorg Med. Chem. 12, 2151–2161 (2004)

    Article  Google Scholar 

  23. C. Narayana, B.V. Ashalatha, S.N. Kumari, Eur. J. Med. Chem. 42, 425–429 (2007)

    Article  Google Scholar 

  24. S.V. Bhandari, A.A. Patil, A.P. Sarkate, S.G. Gore, K.G. Bothra, Bioorg. Med. Chem. 44, 390–400 (2009)

    Article  Google Scholar 

  25. Y.S. Ke, X. Quin, N. Wang, Q. Yang, Eur. J. Med. Chem. 43, 1–9 (2008)

    Article  Google Scholar 

  26. T.A. Vincent, Int. J. Antimicrob. Agents 16, 317–324 (2003)

    Google Scholar 

  27. D.-H. Shi, Acta Cryst E65, o2107 (2009)

    Google Scholar 

  28. X.-S. Lin, Y.-L. Sang, Acta Cryst E65, o1650 (2009)

    Google Scholar 

  29. Y.-M. Hao, Acta Cryst. E65, o2098 (2009)

    Google Scholar 

  30. X.-Y. Qiu, Acta Cryst. E65, o975 (2009)

    Google Scholar 

  31. H. Liu, Acta Cryst. E66, o1582 (2010)

    Google Scholar 

  32. X.-Y. Wang, G.-B. Cao, T. Yang, Acta Cryst. E64, o2022 (2008)

    Google Scholar 

  33. L.-W. Xue, Y.–J. Han, C.-J. Hao, G.-Q. Zhao, Q.-R. Liu, Acta Cryst. E64, o1938 (2008)

    Google Scholar 

  34. H.-W. Huang, Acta Cryst. E66, o3143 (2010)

    Google Scholar 

  35. H.-K. Fun, J. Horkaew, S. Chantrapromma, C. Karalai, Acta Cryst. E68, o1655 (2012)

    Google Scholar 

  36. J.-L. Hou, Acta Cryst. E68, o1352 (2012)

    Google Scholar 

  37. C.-M. Li, H.-Y. Ban, Acta Cryst. E65, o1465 (2009)

    Google Scholar 

  38. S.M. Saad, I. Fatima, S. Perveen, K.M. Khan, S. Yousuf, Acta Cryst. E68, o3499 (2012)

    Google Scholar 

  39. A. Subashini, K. Ramamurthi, H. Stoeckli-Evans, Acta Cryst. C68, o408–o412 (2012)

    Google Scholar 

  40. K. Naseema, K.V. Vijayalakshmi Rao, S., BalakrishnaKalluraya, Curr. Appl. Phys. 10, 1236–1241 (2010)

    Article  Google Scholar 

  41. K. Naseema, K.V. Sujith, K.B. Manjunatha, B. Kalluraya, G. Umesh, R. Vijayalakshmi, Opt. Laser Technol. 42, 741–748 (2010)

    Article  Google Scholar 

  42. S. Vijayakumar, M. Babu, B. Kalluraya, K. Chandrasekharan, Optik 123, 21–25 (2012)

    Article  Google Scholar 

  43. R.B. Moffett, N. Rabjohn, Organic Synthesis, (Wiley, New York, 1963)

    Google Scholar 

  44. R. O’Connor, Ibid. 26, 4375 (1961)

    Google Scholar 

  45. W.O. George, P.S. Mcintyre, Infrared Spectroscopy, Wiley, London, 1987

    Google Scholar 

  46. J. Coates, R.A. Meyers, Interpretation of Infrared Spectra: A Practical Approach (Wiley, Chichester, 2000)

    Google Scholar 

  47. S. Sapna, A. Kumar, P. Tandon, J. Mol. Struct. 981, 1–9 (2010)

    Article  Google Scholar 

  48. V. Krishnakumar, R. John Xavier, Spectrochim. Acta 61A, 253–258 (2005)

    Article  Google Scholar 

  49. A. Altun, K. Golcuk, M. Kumru, J. Mol. Struct. (THEOCHEM) 155, 637–639 (2003)

    Google Scholar 

  50. V. Krishnakumar, N. Prabavathi, Spectrochim. Acta 71A, 449–457 (2008)

    Article  Google Scholar 

  51. Y.-X. Sun, Q.,-L. Hao, Z.,-X. Yu, W.-J. Jiang, L.-D. Lu, X. Wang, Spectrochim. Acta 73A, 892–901 (2009)

    Article  Google Scholar 

  52. V. Krishnakumar, R. John Xavier, Indian J. Pure Appl. Phys. 41, 95–98 (2003)

    Google Scholar 

  53. D.N. Sathyanarayana, Vibrational Spectroscopy Theory and Applications, 2nd edn. (New Age International (P) Limited Publisher, New Delhi, 2004)

    Google Scholar 

  54. N.P. Singh, R.A. Yadav, Indian J. Phys. B 75(4), 347–355 (2001)

    Google Scholar 

  55. C. Stoe, X-Area & X-RED32 Software (Stoe & Cie GmbH, Darmstadt, 2009)

    Google Scholar 

  56. G.M. Sheldrick, Acta Cryst. A64, 112–122 (2008)

    Article  Google Scholar 

  57. S.K. Kurtz, T.T. Perry, J. Appl. Phys. 39, 3798–3813 (1968)

    Article  Google Scholar 

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

    Article  Google Scholar 

  59. A. Subashini, S. Leela, K. Ramamurthi, A. Allakcheeva, H. Stoeckli-Evans, V. Petricek, G. Chapuis, P. Pattison, R. Philip, CrystEngComm 15, 2474–2481 (2013)

    Article  Google Scholar 

  60. R.L. Sutherland, Handbook of Nonlinear Optics (Marcel Dekker Inc., New York, 1996)

    Google Scholar 

  61. A.W. Bauer, W.M.M. Kirby, J.C. Sherris, M. Turck, Am. J. Clin. Pathol. 45, 493–496 (1966)

    Article  Google Scholar 

  62. N.G. Heatley, Biochem. J. 38, 61–65 (1944)

    Article  Google Scholar 

Download references

Acknowledgements

One of the authors (AS) thanks the University Grant Commission, New Delhi for the award of a UGC: Meritorious Fellowship [File No. 4-1/2008 (BSR)]. The author (KR) thanks the Department of Physics and Nanotechnology for extending its facilities created under DST-FIST. Authors thank Central Instrumentation Facility, Pondicherry University, Pondicherry, Department of Visual Communication, Srimad Andavan Arts and Science and College and Advanced Instrumentation Research Facility, Jawaharlal Nehru University, New Delhi for extending the instrumentation facilities.

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Subashini, A., Priyadharsani, P., Thamaraiselvi, K. et al. Studies on growth and characterization of (E)-N′-[4-(dimethylamino) benzylidene]-4-hydroxybenzohydrazide hemihydrate: a nonlinear optical material. J Mater Sci: Mater Electron 30, 2638–2646 (2019). https://doi.org/10.1007/s10854-018-0539-2

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