Effect of Substituent Position on the Properties of Chalcone Isomer Single Crystals

R. Gandhimathi, G. Vinitha, R. Dhanasekaran

Crystal Growth Centre, Anna University, Chennai, India; 2Division of Physics, Vellore Institute of Technology, Chennai, India..

DOI: 10.4236/jcpt.2013.34023                

Abstract

This paper summarizes the synthesis, growth and the effect of the position of the substituent in the thienyl ring and also the properties of the grown chalcone crystals, 2-CTP and 3-CTP. The formation of compound is confirmed by the re- corded H¹NMR spectra. A FT-IR spectrum confirms the presence of all functional groups in both of the crystals. Single crystal XRD reports that even though these two compounds crystallize in monoclinic crystal system, 2-CTP has centro- symmetric P2₁/c space group and 3-CTP has non-centrosymmetric space group P2₁. Thermal properties of grown crys- tals analyzed by TG/DTA study explain that the 3-CTP compound is slightly more stable than 2-CTP. The transparency of these isomers in the vis-IR region has been studied. Second and third order nonlinear optical properties of 3-CTP and 2-CTP crystals have been investigated by powder SHG and Z-scan technique respectively.

Keywords

Solution Growth; Characterization; Chalcones; Nonlinear Optical Materials

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	D. S. Chemla, J. L. Oudar and J. Jerphagnon, “Origin of the Second-Order Optical Susceptibilities of Crystalline Substituted Benzene,” Physical Review B, Vol. 12, No. 10, 1975, pp. 4534-4546. http://dx.doi.org/10.1103/PhysRevB.12.4534
[2]	J. Zyss, “Hyperpolarizabilities of Substituted Conjugated Molecules. III. Study of a Family of Donor-Acceptor Disubstituted Phenyl-Polyenes,” Chemical Physics, Vol. 71, No. 2, 1979, pp. 909-917.
[3]	H.-K. Fun, S. R. Jebas, P. S. Patil and M. Dharmaprakash, “(E)-3-(4-Chlorophenyl)-1-(2-thienyl)prop-2-en-1-oneActa. Cryst,” Acta Crystallographica, Vol. E64, No. 1, 2008, pp. 1592-1593. http://dx.doi.org/10.1107/S1600536808022782
[4]	M. Sheik-Bahae, A. A. Said, T.-H. Wei, D. J. Hagan and E. W. Van Stryland, “Sensitive Measurement of Optical Nonlinearities Using a Single Beam,” IEEE LEOS News Letter, Vol. 21, No. 1, 2007, pp. 17-26.
[5]	A. J. Kiran, K. Chandrasekharan, B. Kallurya and H. D. Shashikala, “Chalcone Possible New materials for Third Order Nonlinear Optics,” In: S. V. Arnold, Ed., Chemical Physics Research Trends, Nova Science Publishers Inc., New York, 2007, pp. 247-257.
[6]	T. Uchida, K. Kozawa, Y. Kimurab and Y. Gotob, “Structural Study on Chalcone Derivatives,” Synthetic Metals, Vol. 71, No. 1-3, 1995, pp. 1705-1706. http://dx.doi.org/10.1016/0379-6779(94)03013-V
[7]	R. Laliberte, J. Manson, H. Warwick and G. Medawar, “Synthesis of New Chalcone Analogues and Derivatives,” Canadian Journal of Chemistry, Vol. 46, No. 11, 1968, pp. 1952-1956. http://dx.doi.org/10.1139/v68-324
[8]	M. A. Hassan, S. Batterjee and L. A. Taib, “Novel Syn- thesis of 1H-Inden-1-Ones and Thienylpropenones in Aqueous Medium,” Journal of the Chinese Chemical So- ciety, Vol. 53, No. 4, 2006, pp. 939-944.
[9]	Y. P. He, G. B. Su, G. M. Yiu, X. J. Huang and R. H. Jang, “Growth and Characterization of a New Organic Nonlinear Optical Crystal: 1-(3-Thienyl)-3-(4-chiorophenyl)- propene-1-one,” Journal of Crystal Growth, Vol. 141, No. 3-4, 1994, pp. 389-392. http://dx.doi.org/10.1016/0022-0248(94)90243-7
[10]	S. A. Basaif, T. R. Sobahi, A. Kh. Khalil and M. A. Has- san, “Stereoselective Crossed-Aldol Condesation of Hetarylmethyl Ketones with Aromatic Aldehydes in Water: Synthesis of (2E)-3-Aryl-1-hetarylprop-2-en-1-ones,” Bulletin of the Korean Chemical Society, Vol. 26, No. 11, 2005, pp. 1677-168.
[11]	Y. Budak, M. B. Gürdere, M. Kececi and M. Ceylan, “Preparation of Diethyl Malonate Adducts from Chalcone Analogs Containing a Thienyl Ring,” Bulletin of the Chemical Society of Ethiopia, Vol. 24, No. 1, 2010, pp. 85-91.
[12]	V. Crasta, V. Ravindrachary, R. F. Bhajantri and R. Gonsalves, “Growth and Characterization of an Organic NLO Crystal: 1-(4-Methylphenyl)-3-(4-ethoxyphenyl)-2-propen-1- one,” Journal of Crystal Growth, Vol. 267, No. 1-2, 2004, pp. 129-133. http://dx.doi.org/10.1016/j.jcrysgro.2004.03.037
[13]	S. B. Mansoor, A. A. Said, T. H. Wei, D. J. Hagan and E. W. Van Stryland, “Sensitive Measurement of Optical Nonlinearities Using a Single Beam,” IEEE Journal of Quantum Electronics, Vol. 26, No. 4, 1990, pp. 760-769.
[14]	H. J. Ravindra, A. J. Kiran, K. Chandraskharan, H. D. Shashikala and S. M. Dharmaprakash, “Third Order Nonlinear Optical Properties and Optical Limiting in Do- nor/Acceptor Substituted 4’-Methoxy Chalcone Derivatives,” Journal of Applied Physics, Vol. B88, No. 1, 2007, pp. 105-110. http://dx.doi.org/10.1007/s00340-007-2677-8
[15]	F. A. Jenkins and H. E. White, “Fundamentals of Optics,” 3rd Edition, MacGraw-Hill, New York, 1957.
[16]	A. M. Nasr, “Determination of Refractive Index and Birefringence of Dye Doped Polycarbonate Films Prepared by Different Techniques,” International Journal of Materials Sciences, Vol. 2, No. 1, 2007, pp. 103-109.
[17]	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. 3798-3813. http://dx.doi.org/10.1063/1.1656857