Abstract
In recent times, there has been considerable research and constant development on second-order nonlinear optical (NLO) materials owing to their potential applications in optical information processing, THz imaging and spectroscopy, telecommunication and optical data storage. A novel organic material 8-hydroxyquinoline 5-chloro-2-hydroxybenzoic acid (8HQ5C) was synthesized, and the single crystals were grown by solution technique. The crystal structure (8HQ5C) was confirmed by single-crystal (SCXRD) X-ray diffraction, and it crystallized in orthorhombic structure with non-centrosymmetric P212121 space group. The different functional groups were identified from Fourier transform infrared (FTIR) spectroscopy. The proton NMR spectral study was helpful to understand the various protons of 8HQ5C structure in its chemical environment. The % of transmittance and absorbance of light by the title crystal was estimated by UV–visible spectral study, and the cutoff wavelength was observed at 460 nm. The thermal nature of the 8HQ5C crystal has been identified by TG-DSC analysis. The mechanical strength of the grown crystal was analyzed through microhardness. Second harmonic generation (SHG) was confirmed through the Kurtz–Perry method, and the efficiency was compared with the value of the prominent KDP crystal. The theoretical computation was made with density functional theory (DFT) B3LYP method 6–311 + + G (d,p) as a basis set. The charge property of the title crystal was described by frontier molecular orbital (FMO) test. The first hyperpolarizability of 8HQ5C was analyzed, and the hydrogen bond of a given molecule was determined through natural bond analysis (NBO).
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References
P.N. Prasad, D.J. Williams, Introduction to nonlinear optical effects in molecules and polymers, 1st edn. (Wiley, New York, 1991)
D.S. Chemla, J. Zyss, Nonlinear optical properties of organic molecules and crystals, 1st edn. (Academic Press, London, 1987)
S. Karthick, K. Thirupugalmani, G. Shanmugam, V. Kannan, S. Brahadeeswaran, Experimental and quantum chemical studies on N-H—O hydrogen bonded helical chain type Morpholinium 2-Chloro-4-Nitrobenzoate: a phase matchable organic nonlinear optical material. J. Mol. Struct. 1156, 264–272 (2018)
K. Nivetha, W. Madhuri, Structural, spectral, thermal, and optical studies of stilbazolium derivative crystal: (E)-4-(3-hydroxy-4-methoxystyryl)-1-methyl pyridinium iodide monohydrate. Optic. Laser. Technol. 109, 496–503 (2019)
K. Senthil, S. Kalainathan, Y. Kondo, F. Hamada, M. Yamada, Investigation on the crystal growth, molecular structure and nonlinear optical susceptibilities of 2-[2- (4-Ethoxy-phenyl) vinyl]-1-ethyl-stilbazolium iodide (EESI) by Z-scan technique using He–Ne laser for third-order nonlinear optical applications. Optic. Laser. Technol. 90, 242–251 (2017)
P. Nagapandiselvi, C. Baby, R. Gopalakrishnan, Self-assembled supramolecular structure of N, N, N0, N0-tetramethylethylenediammonium-bis-(4-nitrophenolate): synthesis, single crystal growth and photo physical properties. RSC Adv. 4, 22350–22358 (2014)
K. Nivetha, S. Kalainathan, A new nonlinear optical stilbazolium family crystal of (E)-1- ethyl-2-(4-nitrostyryl) pyridin-1-ium iodide: synthesis, crystal structure and its third-order nonlinear optical properties. J. Phys. Chem. C 122, 4572–4582 (2018)
M. Hemamalini, W.S. Loh, C.K. Quah, H.K. Fun, Investigations of Supramolecular synthons and structural characterisation of carboxylic acid derivatives. Chem. Cent. J. 8, 31 (2014)
E.M. Filip, I.V. Humelnicu, C.I. Ghirvu, ‗Some aspects of 8-hydroxyquinoline in solvents‘. Acta. Chemica. IASI 17, 85–96 (2009)
M. Karabackak, E. Kose, M. Kurt, FT-Raman, FT-IR spectra and DFT calculations on monomeric and dimeric structures of 5-fluoro-and-5-chloro-salicylic acid. J. Raman Spectrosc. 41, 1085–1097 (2010)
S. Gracin, M.U. Penttila, A.C. Rasmuson, Influence of ultrasound on the nucleation of polymorphs of p-aminobenzoic acid. Cryst. Growth Des. 5, 1787–1794 (2005)
G. Parvathy, R. Kaliammal, K. Velsankar, G. Vinitha, K. Sankaranarayanan, R. Mohankumar, S. Sudhahar, Piperazinium bis (5-chlorosalicylate)-A new third order nonlinear optical single crystal. J. Mol. Struc. 1228, 129728 (2021)
S. Sudhahar, M. Krishnakumar, B.M. Sornamurthy, R. Mohankumar, Synthesis, Crystal growth, structural, thermal, optical and mechanical properties of solution grown 4- methylpyridinium 4-hydroxybenzoate single crystal Spectrochim. Acta. Part A Mol. Biomol. Spectrsc. 118, 929–937 (2014)
G. Socrates, Infrared and raman characteristic group frequencies (Wiley Interscience Publications, New York, 1994)
P. Pavitha, J. Prashanth, G. Ramu, G. Ramesh, K. Mamatha, B. Venkatram Reddy, Synthesis, structural, spectroscopic, anti-cancer and molecular docking studies on novel 2- [(Anthracene-9-ylmethylene)amino]-2-methylpropane-1,3-diol using XRD, FTIR, NMR, UV-Vis spectra and DFT. J. Mol. Struct. 1147, 406–426 (2017)
G. Parvathy, R. Kaliammal, K. Sankaranarayanan, M. Arivanandhan, M. Krishna Kumar, S. Sudhahar, Growth, experimental and theoretical investigations on 4-hydroxy-3- methoxybenzaldehyde 5-chloro-2-hydroxybenzoic acid: a new high second order nonlinear optical material. J. Mol. Struc. 1217, 128406 (2020)
D. Satheesh, R. Roshini, S. Jeevitha, K. Chithra, S.V. Kumar, P. Sellam, Anti-inflammatory and anti-diabetic activity of 8- Hydroxyquinolinium 3,5-Dinitrobenzoate. Chem. Data Collect. 33, 100726 (2021)
D. Satheesh, A. Rajendran, K. Chithra, R. Saravanan, Synthesis of some new protic N1- Benzyl/Butyl-2-methyl-4-nitro-1H-imidazol-3-ium salts with 3,5-Diaminobenzoate, 3,5- Dinitrobenzoate, (E)-3-(4-Hydroxy-3-methoxyphenyl)acrylate and 2-Carboxy-5-nitrobenzoate as organic anions. Results Chem. 2, 100033 (2020)
S.K. Sharma, M.K. Yeshpal Singh, K.S. Sunil Verma, PK Gupta. Bartwal, Cryst. Eng. Comm. 18, 6403–6410 (2016)
R. Gomathi, S. Madeswaran, Structural, thermal and nonlinear optical studies on novel organic cyclohexylammonium hydrogen adipate crystal. Mater. Chem. Phys. 218, 189–195 (2018)
B.R. Lawn, E.R. Fuller, Equilibrium penny like cracks in indentation fracture. J. Mater. Sci. 10, 2016–2024 (1975)
J.M. Linet, S.M.N. Priya, S. Dinakaran, S. Jerome Das, Dielectric and micro hardness studies on L-citrulline and L-ascorbic admixture TGS crystals. Cryst. Res. Tech. 43, 806–810 (2008)
E. Meyer, Untersuchungen über Härteprüfung und Härte Brinell Methoden. Z. Ver. Deut. Ing. 52, 645–835 (1908)
E.M. Onitsch, Over the microhardness of the metals. Mikroskopie 2, 131–151 (1947)
M. Hanneman, Indentation size effect and microhardness study. Metall. Manch 23, 135–139 (1941)
N. Sivakumar, N. Kanagathara, B. Varghese, G. Bhagavannarayana, S. Gunasekaran, G. Anbalagan, Structure, crystal growth, optical and mechanical studies of poly bis (thiourea) silver (I) nitrate single crystal: a new semi organic NLO material. Spectrochim. Acta, Part A 118, 603–613 (2014)
Y. Porter, O.K. Kang Min, N.S.P. Bhuvanesh, P.S. Halasyamani, Synthesis and characterization of Te2SeO7: a powder second-harmonic-generating study of TeO2, Te2SeO7, Te2O5, and TeSeO4. Chem. Mater. 13, 1910–1915 (2001)
D. Xue, S. Zhang, Effect of hydrogen bonds on optical nonlinearities of inorganic crystals. Chem. Phys. Lett. 301, 449–452 (1999)
A. Becke, Phys. Rev. A 38, 3098–3100 (1988)
C. Lee, W. Yang, R. Parr, Phys. Rev. B 37, 785–789 (1988)
M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G.Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M.Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao,H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J.Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K.Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M.Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R.Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W.Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J.Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J.Cioslowski, D.J. Fox, Gaussian 09, Revision E.01, Gaussian, Inc., Wallingford CT, 2009
Gaussview, Version 5, Roy Dennington, Todd keith and John Millam, Semichem Inc. Shawnee Mission, KS, 2009
I. Fleming, Frontier orbitals and organic chemical reactions (John Wiley and Sons, New York, 1976)
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)
T. Koopmans, Ordering of wave functions and eigen energies to the individual electrons of an atom. Physica 1, 104–113 (1933)
C. Andraud, T. Brotin, C. Garcia, F. Pelle, P. Goldner, B. Bigot, A. Collet, J. Am. Chem. Soc. 116, 2094–2102 (1994)
R. Zhang, B. Du, G. Sun, Y. Sun, Spectrochim. Acta Mol. Biomol Spectrosc. 75, 1115–1124 (2010)
D. Kleinman, Phys. Rev. 126, 1977–1979 (1962)
R. Kaliammal, G. Parvathy, R. Mohan Kumar, M. Krishna Kumar, G. Vinitha, S. Sudhahar, Physicochemical and quantum chemical calculations on new bis (2-amino- methylpyridinium 3,4-dimethoxybenzoate) dehydrate organic single crystal for third order nonlinear optical applications. Chin. J. Phys. 72, 100–125 (2021)
A. Reed, L. Curtiss, F. Weinhold, Chem. Rev. 88, 899–926 (1988)
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The authors acknowledge the scheme MHRD-RUSA PHASE-2.0 (grant sanctioned vide Letter No. F.24-51/2014-U, Policy (TN Multi-Gen), Dept. of Edn. Govt. of India, Dt.09.10.2018) New Delhi and DST-PURSE-II New Delhi for a grant. Also, the authors express their thanks to UGC-SAP, DST-FIST and Alagappa University, Karaikudi-03, Tamil Nadu, India.
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Parvathy, G., Kaliammal, R., Velsankar, K. et al. Physicochemical and computational perspectives of 8-hydroxyquinoline 5-chloro-2-hydroxybenzoic acid: a novel second-order nonlinear optical crystal. Appl. Phys. A 127, 957 (2021). https://doi.org/10.1007/s00339-021-05115-2
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DOI: https://doi.org/10.1007/s00339-021-05115-2