Structure–property relation and third-order nonlinear optical studies of two new halogenated chalcones
-
Huey Chong Kwong
,
Shivaraj R. Maidur
Abstract
In the present work, the crystal structure and third-order nonlinear optical (NLO) properties of two novel chalcone derivatives namely (E)-3-(4-bromo-2-fluorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one (I) and (E)-3-(4-bromophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one (II) are investigated by analyzing the packing pattern, intermolecular interaction, Hirshfeld surface analysis and standard Z-scan technique with continuous wave laser at 532 nm. Both compounds are donor-acceptor-acceptor (D–A–A) type intramolecular charge transferring molecule which crystallized in centrosymmetric space group. The existence of C–H···O hydrogen bonds in I and Br···O short contact interactions in II play important roles in their packing pattern and NLO properties. The molecules reveal a strong nonlinear refraction (NLR) and nonlinear susceptibility χ(3) when the donor and acceptor are arranged side-by-side as in compound I. And as the donor and acceptor are aligned on a head-to-head alignment, the molecules divulge a strong third-order nonlinear absorption (NLA) and limiting threshold (LT). The Z-scan results indicate that both compounds would be potential applicants in the development of NLO devices.
Acknowledgements
HCK thanks Malaysian Government for MyBrain15 (MyPhD) scholarship. PSP thank Science and Engineering Research Board (SERB), Government of India, for Start-up research grant under Young scientists scheme (SB/FTP/PS-021/2014). The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Fundamental Research Grant Scheme (FRGS) (203/PFIZIK/6711563). Authors extend their appreciation to Vidya Vikas Research & Development Center for the facilities and encouragement.
References
[1] J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedwhorth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, H. Sasabe, Science1996, 273, 1533.10.1126/science.273.5281.1533Search in Google Scholar
[2] S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J.-L. Brédas, B. M. Pierce, Science1994, 265, 632.10.1126/science.265.5172.632Search in Google Scholar PubMed
[3] C. Li, L. Zhang, M. Yang, H. Wang, Y. Wang, PhRvA1994, 49, 1149.10.1103/PhysRevA.49.1149Search in Google Scholar
[4] J. E. Ehrlich, X. L. Wu, I. Y. S. Lee, Z. Y. Hu, H. Röckel, S. R. Marder, J. W. Perry, OptL1997, 22, 1843.10.1364/OL.22.001843Search in Google Scholar
[5] M. Albota, D. Beljonne, J. L. Brédas, J. E. Ehrlich, J. Y. Fu, A. A. Heikal, S. E. Hess, T. Kogej, M. D. Levin, S. R. Marder, D. McCord-Maughon, J. W. Perry, H. Röckel, M. Rumi, G. Subramaniam, W. W. Webb, X. L. Wu, C. Xu, Science1998, 281, 1653.10.1126/science.281.5383.1653Search in Google Scholar PubMed
[6] C. S. Chidan Kumar, S. Raghavendra, T. S. Chia, S. Chandraju, S. M. Dharmaprakash, H.-K. Fun, C. K. Quah, OptMa2015, 49, 279.10.1016/j.optmat.2015.09.026Search in Google Scholar
[7] T. Chandra Shekhara Shetty, S. Raghavendra, C. S. Chidan Kumar, S. M. Dharmaprakash, Opt. Laser Technol.2016, 77, 23.10.1016/j.optlastec.2015.08.015Search in Google Scholar
[8] J. Coates, in Encyclopedia of Analytical Chemistry, John Wiley & Sons, Ltd, Chichester, 2006.Search in Google Scholar
[9] F. Massicot, A. M. Iriarte, T. Brigaud, A. Lebrun, C. Portella, Org. Biomol. Chem.2011, 9, 600.10.1039/C0OB00518ESearch in Google Scholar PubMed
[10] Y. Wei, J. Tang, X. Cong, X. Zeng, Green Chem.2013, 15, 3165.10.1039/c3gc41403eSearch in Google Scholar
[11] J. J. McKinnon, M. A. Spackman, A. S. Mitchell, AcCrB2004, 60, 627.10.1107/S0108768104020300Search in Google Scholar PubMed
[12] J. J. McKinnon, D. Jayatilaka, M. A. Spackman, Chem. Commun.2007, 3814. Available at: http://pubs.rsc.org/en/Content/ArticleLanding/2007/CC/b704980c#!divAbstract.10.1039/b704980cSearch in Google Scholar PubMed
[13] M. A. Spackman, J. J. McKinnon, CrystEngComm2002, 4, 378.10.1039/B203191BSearch in Google Scholar
[14] M. A. Spackman, D. Jayatilaka, CrystEngComm2009, 11, 19.10.1039/B818330ASearch in Google Scholar
[15] H. N. Pati, U. Das, H. Sakagami, M. Kawase, Q. Chu, Q. Wang, J. P. Stables, J. R. Dimmock, Arch. Pharm.2010, 343, 535.10.1002/ardp.200900308Search in Google Scholar PubMed PubMed Central
[16] M. A. Spackman, J. J. McKinnon, D. Jayatilaka, CrystEngComm2008, 10, 377.Search in Google Scholar
[17] P. S. Patil, S. R. Maidur, S. V. Rao, S. M. Dharmaprakash, Opt. Laser Technol.2016, 81, 70.10.1016/j.optlastec.2016.01.033Search in Google Scholar
[18] A. Ekbote, P. S. Patil, S. R. Maidur, T. S. Chia, C. K. Quah, Dyes Pigm.2017, 139, 720.10.1016/j.dyepig.2017.01.002Search in Google Scholar
[19] S. R. Maidur, P. S. Patil, S. V. Rao, M. Shkir, S. M. Dharmaprakash, Opt. Laser Technol.2017, 97, 219.10.1016/j.optlastec.2017.07.003Search in Google Scholar
[20] Bruker, APEX2, SAINT and SADABS, Bruker AXS Inc., 2009.Search in Google Scholar
[21] G. M. Sheldrick, Acta Crystallogr. Sect. A Found. Crystallogr.2007, 64, 112.10.1107/S0108767307043930Search in Google Scholar PubMed
[22] Bruker, Bruker AXS Inc., Madison. Wisconsin, USA, 2012.Search in Google Scholar
[23] T. Chandra Shekhara Shetty, S. Raghavendra, C. S. Chidan Kumar, S. M. Dharmaprakash, Appl. Phys. B2016, 122, 205.10.1007/s00340-016-6478-9Search in Google Scholar
[24] A. Sim, C. S. Chidan Kumar, H. C. Kwong, L. Y. Then, Y.-F. Win, C. K. Quah, S. Naveen, S. Chandraju, N. K. Lokanath, I. Warad, Acta Cryst. 2017, 73, 896.Search in Google Scholar
[25] S. K. Wolff, D. J. Grimwood, J. J. McKinnon, M. J. Turner, D. Jayatilaka, M. A. Spackman, University of Western Australia, Australia, 2012.Search in Google Scholar
[26] M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, E. W. V. Stryland, IEEE J. Quantum Electron.1990, 26, 760.10.1109/3.53394Search in Google Scholar
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The online version of this article offers supplementary material (https://doi.org/10.1515/zkri-2017-2098).
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- Frontmatter
- Graphical Synopsis
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- The ternary phases Cu1.5−xLi1+x Sb and Cu4+xLi1−x Sb2, and their structural relations
- Synthesis and crystal structures of the new ternary borides Fe3Al2B2 and Ru9Al3B8 and the confirmation of Ru4Al3B2 and Ru9Al5B8−x (x≈2)
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- Role of defectivity on the crystallography of martensitic transformations in Ti50Ni40Cu10: an XRD investigation
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- Structure–property relation and third-order nonlinear optical studies of two new halogenated chalcones
