Abstract
A novel azo dye compound, Ethyl (E)-4-((5-hydroxy-3,4-bis(hydroxyl methyl)-6-methyl. pyridin-2-yl)diazenyl)benzoate (EAB), have been synthesized by the coupling reaction and characterized by FT-IR, 1H-and 13C-NMR, Mass, and UV–visible spectroscopies. The nonlinear optical (NLO) properties of the EAB compound via the finding of the nonlinear refractive index (NRI) using continuous wave (cw), low power 473 nm, TEM00 mode laser beam have been studied via the diffraction patterns (DPs) and the Z-scan. Effect of power input of the laser beam, types of beam wavefront and temporal variation of the DPs are discussed. The all-optical switching (AOS) using two laser beams is proved to occur in this compound.
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References
Abdel-Kader, N.S., Abdel-Latif, S.A., El-Ansarya, A.L., Sayed, A.G.: Spectroscopic studies, density functional theory calculations, non-linear optical properties, biological activity of 1-hydroxy-4-((4-(N-(pyrimidin-2-yl)sulfamoyl)phenyl)diazenyl)-2-naphthoic acid and its chelates with Nickel (II), Copper (II), Zinc (II) and Palladium (II) metal ions. J. Molec. Struc. 1223, 129203 (2021)
Abdullmajed, H.A., Sultan, H.A., Al-Asadi, R.H., Hassan, Q.M.A., Ali, A.A., Emshary, C.A.: Synthesis, DFT calculations and optical nonlinear properties of two derived Schiff base compounds from ethyl-4-amino benzoate. Phys. Scr. 97, 025809 (2022a)
Abu El-Fadl, A., Mohamad, G.A., Abd El-Moiz, A.B., Rashad, M.: Optical constants of Zn1−xLixO films prepared by chemical bath deposition technique. Phys. B 366, 44–54 (2005)
Agrawal, G.: Modulation, instability induced by cross-phase modulation. Phys. Rev. Lett. 59, 800–803 (1987)
Al-Asadi, R.H.: Synthesis and molecular structure study of new organotellurium and organomercury compounds based on 4-bromonaphthalen-1-amine. Russ. J. Gen. Chem. 90, 1744–1749 (2020)
Al-Hamdani, U.J., Hassan, Q.M.A., Emshary, C.A., Sultan, H.A., Dhumad, A.M., Al-Jaber, A.A.: All optical switching and the optical nonlinear properties of 4-(benzothiazolyldiazenyl)-3-chlorophenyl 4-(nonylthio)benzoate (EB-3Cl). Optik 248, 168196 (2021)
Alharis, R.A., Al-Asadi, R.H., Hassan, D.A.: New mercurated and Tellurated sulpha compounds: synthesis, Invitro anticancer study and DFT calculation. Egypt. J. Chem. 64, 5755–5764 (2021)
Ali, Q.M., Palanisamy, P.K.: Optical phase conjugation by degenerate four-wave mixing in basic green 1 dye-doped gelatin film using He–Ne laser. Opt. Las. Technol. 39, 1262–1268 (2007)
Ali, Q.M., Palanisamy, P.K., Manickasundaram, S.P.: Kannan, Sudan IV dye based poly(alkyloxymethacrylate)films for optical data storage. Opt. Commun. 267, 236–243 (2006)
Ali, H., Majeed, H., Al-Asadi, I., Abdulredha, A., Hussain, A.: Structures effect of two azo dyes associated with their antimicrobial activity, J. Chem. Biolo. Phys. Sci. 8, 171–185 (2018)
Ali, S.A., Hassan, Q.M.A., Emshary, C.A., Sultan, H.A.: Characterizing optical and morphological properties of Eriochrome Black T doped polyvinyl alcohol film. Phys. Scr. 95, 095814 (2020)
Al-Masoudi, W.A., Al-Asadi, R.H., Othman, R.M., Al-Masoudi, N.A.: Synthesis, antimicrobial activity, computational and modeling studies of some new organotellurium compounds containing azo moities. Euro. J. Chem. 6, 374–380 (2015)
Al-Timimy, K.H.A., Qusay, M.A., Hassan, H.A., Sultan, C.A., Emshary: Solvents effect on the optical nonlinear properties of the sudan iv. Optik 224, 165398 (2020)
Ambs, P.: Optical computing: a 60-year adventure. Adv. Opt. Technol. 2010, 1–15 (2010). https://doi.org/10.1155/2010/372652
Benkhay, S., Rabet, S.M., El Harfi, A.: Classifications, properties, recent synthesis and applications of azo dyes. Heliyon 6, e03271 (2020)
Bohac, L.: The soliton transmission in optical fibers. Inf. Commun. Technol. Serv. 8, 107–110 (2010)
Child, R.G., Wilkinson, R.G., Tomcu-Fucik, A.: Effect of substrate orientation of the adhesion of polymer joints. J. Chem. Soc. 87, 6031–6038 (1977)
Dadrass, A., Rahchamani, H.: Synthesis of organophosphorus complexes and structural characterization of two dimeric triphenylphosphinne complexes of mercury(II) ions from dimeric complexes of [4-methylbenzoylmethylene tri-p-tolylphosphine mercury(II) halides]. J. Chil. Chem. Soc. 61, 2968–2972 (2016)
Dhaef, H.K., Al-Asadi, R.H., Shenta, A.A., Mohammed, M.K.: Novel bis maleimide derivatives containing azo group: synthesis, corrosion inhibition, and theoretical study. Indones. J. Chem. 21, 1212–1220 (2021)
Dhumad, A.M., Hassan, Q.M.A., Tarek Fahad, C.A., Emshary, N., Raheem, A., Sultan, H.A.: Synthesis, structural characterization and optical nonlinear properties of two azo-β-diketones. J. Molec. Struct. 1235, 130196 (2021a)
Dhumad, A.M., Qusay, M.A., Hassan, C.A.E., Fahad, T., Raheem, N.A., Sultan, H.A.: Nonlinear optical properties investigation of a newly synthesised Azo-(β)-diketone dye. J. Photochem. Photobio. A Chem. 418, 113429 (2021b)
Elias, R.S., Hassan, Q.M.A., Sultan, H.A., Al-Asadi, A.S., Saeed, B.A., Emshary, C.A.: Thermal nonlinearities for three curcuminoids measured by diffraction ring patterns and Z-scan under visible CW laser illumination. Opt. Las. Technol. 107, 131–141 (2018)
Elias, R.S., Hassan, Q.M.A., Emshary, C.A., Sultan, H.A., Saeed, B.A.: Formation and temporal evolution of diffraction ring patterns in a newly prepared dihydropyridone, Spectroch. Acta Part A Molec. Biomol. Spec. 223, 117297 (2019)
Emshary, C.A., Ali, I.M., Hassan, Q.M.A., Sultan, H.A.: Linear and nonlinear optical properties of potassium dichromate in solution and solid polymer film. Phys. B 613, 413014 (2021a)
Emshary, C.A., Hassan, Q.M.A., Bakr, H., Sultan, H.A.: Determination of the optical constants, nonlinear optical parameters and threshold limiting of methyl red-epoxy resin film. Phys. B 622, 413354 (2021b)
Farghaly, T.A., Abdallah, Z.A.: Synthesis, azo-hydrazone tautomerism and antitumor screening of N-(3-ethoxycarbonyl 4, 5, 6, 7-tetrahydro-benzo[b]thien-2-yl)-2-arylhydrazono-3-oxobutanamide derivatives. ARKIVOC 17, 295–305 (2008)
Fayadh, R.H., Ali, A.A., F. M. Al–Jabri,: Synthesis and identification symmetrically azo dyes derived from sulfa compounds and spectrophotometric study of nickel (II) complexes with prepared dyes. IJETR 3, 25–28 (2015)
Ghanavatkar, C.W., Mishra, V.R., Sharma, S., Mathew, E., Chitrambalam, S., Joe, I.H., Nethi, S.N.: Red Emitting Hydroxybenzazole (HBX) based azo dyes: linear and non linear optical properties, optical limiting, z scan analysis with DFT assessments. J. Fluor. 30, 335–346 (2020)
Jassem, A.M., Qusay, M.A., Hassan, C.A., Emshary, H.A., Sultan, F.A., AlmashalRadhi, W.A.: Synthesis and optical nonlinear properties performance of azonaphthol dye. Phys. Scr. 96, 025503 (2021)
Jia, Y., Shan, Y., Wu, L., Dai, X., Fan, D., Xiang, Y.: Broad band nonlinear optical resonance and all-optical switching of liquid phase exfoliated tungsten diselenide. Phot. Res. 6, 1040–1046 (2018)
Jia, Y., Liao, Y., Leiming, Wu., Shan, Y., Dai, X., Cai, H., Xiang, Y.: Dianyuan Fan Nonlinear optical response, all optical switching, and all optical information conversion in NbSe2 nanosheets based on spatial self-phase modulation. Nanoscale 11, 4515–4522 (2019)
Jones, D.J., Diddams, S.A., Taubman, M.S., Cundiff, S.T., Ma, L.-S., Hall, J.L.: Frequency comb generation using femtosecond pulses and cross-phase modulation in optical fiber at arbitrary center frequencies. Opt. Lett. 25, 308–310 (2000)
Khalaf, S.K., Hassan, Q.M.A., Emshary, C.A., Sultan, H.A.: Concentration effect on optical properties and optical limiting of PVA doped with nigrosin films. J. Photochem. Photobio. A Chem. 427, 113809 (2022)
Kirkan, B., Gup, R.: Synthesis of new azo dyes and copper (II) complexes derived from barbituric acid and 4-aminobenzoylhydrazone. Turk. J. Chem. 32, 9–17 (2008)
Langhals, H: Color chemistry; synthesis, properties and Application of organic dyes and pigments , 3rd revised edition, Book Review, (2004)
Manickasundaram, S., Kannan, P., Qusay, M.A., HassanPalanisamy, P.K.: Azo dye based poly(alkyloxymethacrylate)s and their spacer effect on optical data storage. J Mater. Sci: Mater. Electron. 19, 1045–1053 (2008a)
Manickasundaram, S., Kannan, P., Hassan, Q.M.A., Palanisamy, P.K.: Holographic grating formation in poly(methacrylate) containing pendant xanthene dyes. Optoelec. Adv. Mater. Rap. Commun. 2, 324–331 (2008b)
Manickasundaram, S., Kannan, P., Kumaran, R., Velu, R., Ramamurthy, P., Qusay, M.A., Hassan, P.K., Palanisamy, S., SenthilNarayanan, S.S.: Holographic grating studies in pendant xanthene dyes containing poly(alkyloxymethacrylate)s. J. Mat. Sci. Mat. Electron. 22, 25–34 (2011)
Matsuoka, S., Miyanaga, N., Amano, S., Nakaosuka, M.: Frequency modulation controlled by cross-phase modulation in optical fiber. Opt. Lett. 22, 25–276 (1997)
Mishra, A.K., Tewari, S.P.: 7-Hydroxy-6-methoxy-coumarian to be a multifunctional bioactive natural molecule: a theoretical study. Mater. Tod. Proc. 15, 400–408 (2019)
Mohammed, H.: Synthesis, identification, and biological study for some complexes of azo dye having theophylline. Sci. Wor. J. 2021, 1–9 (2021)
Mutlaq, D.Z., Hassan, Q.M.A., Sultan, H.A., Emshary, C.A.: The optical nonlinear properties of a new synthesized azo-nitrone compound. Opt. Mater. 113, 110815 (2021)
Ogusu, K., Kohtani, Y., Shao, H.: Laser-induced diffraction rings from an absorbing solution. Opt. Rev. 3, 232–234 (1996)
Otutu, J.O.: Synthesis and application of azo dyes derived from 2-amino-1, 3,4-thiadiazole-2-thiol on polyester fibre. IJRRAS 15, 292–296 (2013)
Qusay, M.A., Hassan, C.A., Emshary, H.A., Sultan,: Investigating the optical nonlinear properties and limiting optical of eosin methylene blue solution using a cw laser beam. Phys. Scr. 96, 095503 (2021)
Ruddock, I.S.: Nonlinear optical harmonic generation. Eur. J. Phys. 15, 53–58 (1994)
Saeed, B.A., Hassan, Q.M.A., Emshary, C.A., Sultan, H.A., Elias, R.S.: The nonlinear optical properties of two dihydropyridones derived from curcumin, Spectrochim. Acta Part A Molec. Biomol. Spec. 240, 118622 (2020)
Shabeeb, G.M., Emshary, C.A., Hassan, Q.M.A., Sultan, H.A.: Investigating the nonlinear optical properties of poly eosin-Y phthalate solution under irradiation with low power visible CW laser light. Phys. B 578, 411847 (2020)
Shan, Y., Tang, J., Wa, L., Ln, S., Dain, X.: Spatial self-phase nodulation and all-optical switching of graphene oxciz dimensional martials. J. Cent. South Univ. 26, 2295–2306 (2014)
Sheik-Bahae, M., Said, A.A., Van Stryland, E.W.: High sensitivity single beam n2 measurements. Opt. Lett. 14, 955–957 (1989)
Sheik-Bahae, M., Said, A.A., Wei, T., Hagan, D.J., Van Stryland, E.W.: Sensitive measurement of optical nonlinearities using a single beam. IEEE J. Quant. Electron. E 26, 760–769 (1990)
Shen, Y., Tang, J., Wu, L., Lu, S., Dai, X., Xiang, Y.: Spatial self-phase modulation and all-optical switching of grapheme oxide dispersions. J. Allo. Comp. 771, 900–904 (2019)
Sidir, Y.G., Sidir, I., Berber, H., Tasal, E.: UV-spectral changes for some azo compounds in the presence of different solvents. J. Molec. Liq. 162, 148–154 (2011)
Sultan, H.A., Dhumad, A.M., Hassan, Q.M.A., Tarek Fahad, C.A., Emshary, N.A., Raheem,: Synthesis, characterization and the nonlinear optical properties of newly synthesized 4-((1,3-dioxo-1-phenylbutan-2-yl)diazenyl) benzenesulfonamide, Spectroch. Act. Part A Mole. Biomolec. Spec. 251, 119487 (2021)
Tahir, T., Ashfaq, M., Saleem, M., Rafiq, M., Imran Shahzad, M., Kotwica-Mojzych, K., Mojzych, M.: Pyridine scaffolds, phenols and derivatives of azo moiety: curr. Therap. Perspe. Molec. 26, 4871–4888 (2021)
Villafranca, A.B., Saravanamuttu, K.: Diversity and slow dynamics of diffraction ring patterns:a comprehensive study of spatial self-phase modulation in a photopolymer. J. Opt. Soc. Am. B 29, 2357–2372 (2012)
Zhang, X.J., Yuan, Z.H., Yang, R.X., He, Y.I., Qin, Y.I., Xiao, S., He, J.: A review on spatial self-phase modulation of two dimensional materials. J. Cet. South Univ. 26, 2295–2306 (2019)
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Qusay M. A. Hassan and Rafid H. Al. Asadi participated in the characterization and analysis of the results, and H. A. Sultan and Hasanain A. Abdullmajed wrote the manuscript, and Asaad A. Ali and C. A. Emshary wrote the main manuscript text–review & editing. All authors reviewed the manuscript."
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Hassan, Q.M.A., Al-Asadi, R.H., Sultan, H.A. et al. A novel azo compound derived from ethyl-4-amino benzoate: synthesis, nonlinear optical properties and DFT investigations. Opt Quant Electron 55, 392 (2023). https://doi.org/10.1007/s11082-023-04660-9
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DOI: https://doi.org/10.1007/s11082-023-04660-9