Second Harmonic Generation in Some Donor-Acceptor Substituted Chalcone Derivatives
Affiliation(s)
Department of Physics, K.L.E. Institute of Technology, Hubli, India. Department of Physics, K.L.S. Vishwanathrao Deshpande Rural Institute of Technology, Hliyal, India. Department of Physics, S.T.J. Institute of Technology, Ranebennur, India. Materials Characterization Division, National Physical Laboratory, New Delhi, India..
Department of Physics, K.L.E. Institute of Technology, Hubli, India. Department of Physics, K.L.S. Vishwanathrao Deshpande Rural Institute of Technology, Hliyal, India. Department of Physics, S.T.J. Institute of Technology, Ranebennur, India. Materials Characterization Division, National Physical Laboratory, New Delhi, India..
ABSTRACT
A series of five chalcone derivatives with different substituents in para and meta posions have been synthesized, and single crystals were successfully grown in aceton solution by slow evaporation solution growth technique (SESGT). Single crystal X-ray studies revealed that all the crystals crystallized in noncentrosymmetric space group with their molecular dipoles perfectly aligned in a direction-favorable for large nonlinear optical effects. Kurtz powder tests revealed that all five materials have second-harmonic-generating properties with maximum efficiencies of approximately 14 times that of urea standard. UV-vis-NIR spectroscopy and thermogravimetric analyses are also presented for all of the reported materials. Among the five chalcones, high quality single crystals of 4-Methoxy-4'-chlorochalcone were grown by SESGT, and its crystalline perection were studied by using a high resolution X-ray diffractometry (HRXRD).
A series of five chalcone derivatives with different substituents in para and meta posions have been synthesized, and single crystals were successfully grown in aceton solution by slow evaporation solution growth technique (SESGT). Single crystal X-ray studies revealed that all the crystals crystallized in noncentrosymmetric space group with their molecular dipoles perfectly aligned in a direction-favorable for large nonlinear optical effects. Kurtz powder tests revealed that all five materials have second-harmonic-generating properties with maximum efficiencies of approximately 14 times that of urea standard. UV-vis-NIR spectroscopy and thermogravimetric analyses are also presented for all of the reported materials. Among the five chalcones, high quality single crystals of 4-Methoxy-4'-chlorochalcone were grown by SESGT, and its crystalline perection were studied by using a high resolution X-ray diffractometry (HRXRD).
KEYWORDS
Nonlinear Optical Materials; Organic Compounds; Crystal Growth; Second Harmonic Generation; TGA/DTA
Nonlinear Optical Materials; Organic Compounds; Crystal Growth; Second Harmonic Generation; TGA/DTA
Cite this paper
P. Patil, V. Bhumannavar, M. Bannur, H. Kulkarni and G. Bhagavannarayana, "Second Harmonic Generation in Some Donor-Acceptor Substituted Chalcone Derivatives," Journal of Crystallization Process and Technology, Vol. 3 No. 3, 2013, pp. 108-117. doi: 10.4236/jcpt.2013.33018.
P. Patil, V. Bhumannavar, M. Bannur, H. Kulkarni and G. Bhagavannarayana, "Second Harmonic Generation in Some Donor-Acceptor Substituted Chalcone Derivatives," Journal of Crystallization Process and Technology, Vol. 3 No. 3, 2013, pp. 108-117. doi: 10.4236/jcpt.2013.33018.
References
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Dharmaprakash, “(E)-1-(3-Bromophenyl)-3-(4-ethoxyph- enyl)prop-2-en-1-one,” Acta Crystallographica Section E, Vol. E64, No. 7, 2008, pp. o1356-o1357. doi:10.1107/S1600536808018850 [17] G. R. Desiraju and T. Steiner, “The Weak Hydrogen Band in Structural Chemistry and Biology,” Oxford University Press, Oxford, 1999. [18] K. M. Sureshan, T. Uchimaru, Y. Yao, Y. Watanabe, “Strength from Weakness: CH…π Stabilized Conformational Tuning of Benzyl Ethers and a Consequent Co- Operative Edge-to-Face CH Network,” CrystEngComm, Vol. 10, No, 5, 2008, pp. 493-496. doi:10.1039/b718099c [19] R. W. Munn and C. N. Ioronside, “Principles and Applications of Nonlinear Optical Materials,” Chapman and Hell, London, 1993. doi:10.1007/978-94-011-2158-3 [20] J. M. Cole, J. A. K. Howard and G. J. MCIntyre, “Influence of Hydrogen Bonding on the Second Harmonic Generation Effect: Neutron Diffraction Study of 4-Nitro-4’-Methylbenzylidene Aniline,” Acta Crystallographica Section B, Vol. B57, No. 3, 2001, pp. 410-414. doi:10.1107/S0108768101002154 [21] W. Tam, B. Guerin, J. C. Calabrese and S. H. Stevenson, “3-Methyl-4-methoxy-4’-nitrostilbene (MMONS): Crystal Structure of a Highly Efficient Material for Second- Harmonic Generation,” Chemical Physics Letters, Vol. 154, No. 2, 1989, pp. 93-96. doi:10.1016/S0009-2614(89)87265-3 [22] P. Poornesh, K. Ravi, G. Umesh, P. K. Hegde, M. G. Manjunatha, K. B. Manjunatha and A. V. Adhikari, “3,3’-Benzene1,4-diylbis[1-(substituted)phenylprop-2-en-1-one] Derivatives: A New Class of Materials for Third-Order Nonlinear Optical Applications,” Optics Communications, Vol. 283, No.7, 2010, pp. 1519-1527. doi:10.1016/j.optcom.2009.12.015 [23] G. Bhagavannarayana, R. V. Ananthamurthy, G. C. Budakoti, B. Kumar and K. S. Bartwal, “A Study of the Effect of Annealing on Fe-Doped LiNbO3 by HRXRD, XRT and FT-IR,” Journal of Applied Crystallography, Vol. 38, No. 3, 2005, pp. 768-771. doi:10.1107/S0021889805023745
[1] P. N. Prasad and D. J. Williams, “Introduction to Nonlinear Optical Effects in Organic Molecules and Polymers,” Wiley, New York, 1991. [2] D. S. Chemla and J. Zyss, “Nonlinear Optical Properties of Organic Molecules and Crystals,” Academic Press, Orlando, 1987. [3] R. L. Sutherland, D. G. McLean and S. Kirkpatrick, “Handbook of Nonlinear Optics,” 2nd Edition, Marcel Dekker, New York, 2003. doi:10.1201/9780203912539 [4] P. S. Patil, S. M. Dharmaprakash, H.-K. Fun and M. S. Karthikeyan, “Synthesis, Growth, and Characterization of 4-OCH3-40-Nitrochalcone Single Crystal: A Potential NLO Material,” Journal of Crystal Growth, Vol. 297, No. 1, 2006, pp. 111-116. doi:10.1016/j.jcrysgro.2006.09.017 [5] B. Gu, W. Ji, P. S. Patil and S. M. Dharmaprakash, “Ultrafast Optical Nonlinearities and Figures of Merit in Acceptor-Substituted 3,4,5-Trimethoxy Chalcone Derivatives: Structure-Property Relationships,” Journal of Applied Physics, Vol. 103, No. 10, 2008, Article ID: 103511. doi:10.1063/1.2924419 [6] B. Gu, W. Ji, X.-Q. Huang, P. S. Patil and S. M. Dharmaprakash, “Nonlinear Optical Properties of 2,4,5-Trimethoxy-4’-Nitrochalcone: Observation of Two-Photon-Induced Excited-State Nonlinearities,” Optics Express, Vol. 17, No. 2, 2009, pp. 1126-1135. doi:10.1364/OE.17.001126 [7] J. W. Chen, X. Q. Wang, Q. Ren, P. S. Patil, T. B. Li, H. L. Yang, J. N. Zhang , G. C. Li and L. Y. Zhu, “Investigation of Third-Order Nonlinear Optical Properties of NNDC-Doped PMMA Thin Films by Z-Scan Technique,” Applied Physics A, Vol. 105, No. 3, 2011, pp. 723-731. doi:10.1007/s00339-011-6628-1 [8] E. P. Kohler and H. M. Chadwell, “Organic Syntheses,” Collective, Vol. 5, 1941, p. 78. [9] S. K. Kurtz and T. T. Perry, “A Powder Technique for the Evaluation of Nonlinear Optical Materials,” Journal of Applied Physics, Vol. 39, No. 8, 1968, pp. 3798-3814. doi:10.1063/1.1656857 [10] K. Lal and G. Bhagavannarayana, “A High-Resolution Diffuse X-Ray Scattering Study of Defects in Dislocation-Free Silicon Crystals Grown by the Float-Zone Method and Comparison with Czochralski-Grown Crystals,” Journal of Applied Crystallography, Vol. 22, No. 3, 1989, pp. 209-215. doi:10.1107/S0021889888014062 [11] G. Bhagavannarayana, S. Parthiban and S. Meenakshi-sundaram, “Enhancement of Crystalline Perfection by Organic Dopants in ZTS, ADP and KHP Crystals as Investigated by High-Resolution XRD and SEM,” Journal of Applied Crystallography, Vol. 39, No. 6, 2006, pp. 784-790. doi:10.1107/S0021889806033139 [12] W. T. A. Harrison, H. S. Yathirajan, B. K. Sarojini, B. Narayana and J. Indira, “1-(4-Chlorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one,” Acta Crystallographica Section E, Vol. E62, No. 4, 2006, pp. o1647-o1649. doi:10.1107/S1600536806010865 [13] P. S. Patil, J. B. J., Teh, H.-K. Fun, H. B. R. Babu, I. A. Razak and S. M. Dharmaprakash, “3-(3-Methoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one,” Acta Crystallographica Section E, Vol. E63, No. 4, 2007, pp. o1895-o1896. doi:10.1107/S160053680701255X [14] P. S. Patil, H.-K. Fun, S. Chantrapromma and S. M. Dharmaprakash, “1-(4-Chlorophenyl)-3-(4-ethoxy phenyl) prop-2-en-1-one,” Acta Crystallographica Section E, Vol. 63, No. 5, 2007, pp. o2497-o2498. doi:10.1107/S1600536807017394 [15] H.-K. Fun, P. S. Patil, S. M. Dharmaprakash and S. Chantrapromma, “1-(4-Bromophenyl)-3-(4-ethoxyphenyl) prop-2-en-1-one,” Acta Crystallographica Section E, Vol. E64, No. 8, 2008, pp. o1540-o1541. doi:10.1107/S1600536808021776 [16] H.-K. Fun, S. Chantrapromma, P. S. Patil and S. M. Dharmaprakash, “(E)-1-(3-Bromophenyl)-3-(4-ethoxyph- enyl)prop-2-en-1-one,” Acta Crystallographica Section E, Vol. E64, No. 7, 2008, pp. o1356-o1357. doi:10.1107/S1600536808018850 [17] G. R. Desiraju and T. Steiner, “The Weak Hydrogen Band in Structural Chemistry and Biology,” Oxford University Press, Oxford, 1999. [18] K. M. Sureshan, T. Uchimaru, Y. Yao, Y. Watanabe, “Strength from Weakness: CH…π Stabilized Conformational Tuning of Benzyl Ethers and a Consequent Co- Operative Edge-to-Face CH Network,” CrystEngComm, Vol. 10, No, 5, 2008, pp. 493-496. doi:10.1039/b718099c [19] R. W. Munn and C. N. Ioronside, “Principles and Applications of Nonlinear Optical Materials,” Chapman and Hell, London, 1993. doi:10.1007/978-94-011-2158-3 [20] J. M. Cole, J. A. K. Howard and G. J. MCIntyre, “Influence of Hydrogen Bonding on the Second Harmonic Generation Effect: Neutron Diffraction Study of 4-Nitro-4’-Methylbenzylidene Aniline,” Acta Crystallographica Section B, Vol. B57, No. 3, 2001, pp. 410-414. doi:10.1107/S0108768101002154 [21] W. Tam, B. Guerin, J. C. Calabrese and S. H. Stevenson, “3-Methyl-4-methoxy-4’-nitrostilbene (MMONS): Crystal Structure of a Highly Efficient Material for Second- Harmonic Generation,” Chemical Physics Letters, Vol. 154, No. 2, 1989, pp. 93-96. doi:10.1016/S0009-2614(89)87265-3 [22] P. Poornesh, K. Ravi, G. Umesh, P. K. Hegde, M. G. Manjunatha, K. B. Manjunatha and A. V. Adhikari, “3,3’-Benzene1,4-diylbis[1-(substituted)phenylprop-2-en-1-one] Derivatives: A New Class of Materials for Third-Order Nonlinear Optical Applications,” Optics Communications, Vol. 283, No.7, 2010, pp. 1519-1527. doi:10.1016/j.optcom.2009.12.015 [23] G. Bhagavannarayana, R. V. Ananthamurthy, G. C. Budakoti, B. Kumar and K. S. Bartwal, “A Study of the Effect of Annealing on Fe-Doped LiNbO3 by HRXRD, XRT and FT-IR,” Journal of Applied Crystallography, Vol. 38, No. 3, 2005, pp. 768-771. doi:10.1107/S0021889805023745