Skip to main content
Erschienen in: Optical and Quantum Electronics 2/2020

01.02.2020

Impact of amino acids, organic solvents and surfactants on azo-hydrazone tautomerism in Methyl Red: spectral-luminescent and nonlinear optical properties

verfasst von: Soheil Sharifi, Muhammad Faizan Nazar, Forough Rakhshanizadeh, Seyed Ahmad Sangsefedi, Afshin Azarpour

Erschienen in: Optical and Quantum Electronics | Ausgabe 2/2020

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

Azo-linkage in compounds offer broad-spectrum photochromic and nonlinear optical (NLO) properties owing to their architectural flexibility. The present work reports the effects of amino acids, organic solvents and ionic surfactants on the azo-hydrazone tautomerism and hence NLO properties of Methyl Red (MR) dye via the Z-scan technique and spectral-luminescent measurements. From the spectral measurements, the azo-hydrazone transition in MR was observed with the addition of amino acids (l-Phenylalanine and l-Alanine) and ionic surfactants (AOT and CTAB) probably due to the charge interaction. While, this azo-hydrazone switching was not observed with the change of solvent polarity. Moreover, with the provision of the quantum perturbation theory, it was observed that the NLO values of MR also transmuted by changing the concentration of amino acids and surfactants as well as solvent polarity probably due to the fluctuation of the dipole moment of dye during tautomerism and thermal conductivity of solvent, respectively. The results can be integrated into the possible future applications of azo-based molecules in novel photonic and optoelectronic devices.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Wirtschaft"

Online-Abonnement

Mit Springer Professional "Wirtschaft" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 340 Zeitschriften

aus folgenden Fachgebieten:

  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Versicherung + Risiko




Jetzt Wissensvorsprung sichern!

Literatur
Zurück zum Zitat Azarpour, A., Sharifi, S., Rakhshanizadeh, F.: Nonlinear optical properties of crocin: from bulk solvent to nano-confined droplet. J. Mol. Liq. 252, 279–288 (2018)CrossRef Azarpour, A., Sharifi, S., Rakhshanizadeh, F.: Nonlinear optical properties of crocin: from bulk solvent to nano-confined droplet. J. Mol. Liq. 252, 279–288 (2018)CrossRef
Zurück zum Zitat Bronner, C., Priewisch, B., Rück-Braun, K., Tegeder, P.: Photoisomerization of an Azobenzene on the Bi(111) Surface. J. Phys. Chem. C 117, 27031–27038 (2013)CrossRef Bronner, C., Priewisch, B., Rück-Braun, K., Tegeder, P.: Photoisomerization of an Azobenzene on the Bi(111) Surface. J. Phys. Chem. C 117, 27031–27038 (2013)CrossRef
Zurück zum Zitat Christodoulides, D.N., Khoo, I.C., Salamo, G.J., Stegeman, G.I., Van Stryland, E.W.: Nonlinear refraction and absorption: mechanisms and magnitudes. Adv. Opt. Photonics 2, 60–200 (2010)ADSCrossRef Christodoulides, D.N., Khoo, I.C., Salamo, G.J., Stegeman, G.I., Van Stryland, E.W.: Nonlinear refraction and absorption: mechanisms and magnitudes. Adv. Opt. Photonics 2, 60–200 (2010)ADSCrossRef
Zurück zum Zitat Couris, S., Koudoumas, E., Rutht, A.A., Leach, S.: Concentration and wavelength dependence of the effective third-order susceptibility and optical limiting of CSOin toluene solution. Phys. B At. Mol. Opt. Phys. 28, 4537–4554 (1995)ADSCrossRef Couris, S., Koudoumas, E., Rutht, A.A., Leach, S.: Concentration and wavelength dependence of the effective third-order susceptibility and optical limiting of CSOin toluene solution. Phys. B At. Mol. Opt. Phys. 28, 4537–4554 (1995)ADSCrossRef
Zurück zum Zitat Fuks-Janczarek, I., Luc, J., Sahraoui, B., Dumur, F., Hudhomme, P., Berdowski, J., Kityk, I.V.: Third-order nonlinear optical figure of merits for conjugated TTF-quinone molecules. J. Phys. Chem. B 109, 10179–10183 (2005)CrossRef Fuks-Janczarek, I., Luc, J., Sahraoui, B., Dumur, F., Hudhomme, P., Berdowski, J., Kityk, I.V.: Third-order nonlinear optical figure of merits for conjugated TTF-quinone molecules. J. Phys. Chem. B 109, 10179–10183 (2005)CrossRef
Zurück zum Zitat Gayathri, C., Ramalingam, A.: Single-beam Z-scan measurement of the third-order optical nonlinearities of azo dyes. Spectrochim. Acta Part A 68, 578–582 (2007)ADSCrossRef Gayathri, C., Ramalingam, A.: Single-beam Z-scan measurement of the third-order optical nonlinearities of azo dyes. Spectrochim. Acta Part A 68, 578–582 (2007)ADSCrossRef
Zurück zum Zitat Gulseven, Y., Sidir, I.: Solvent effect on the absorption and fluorescence spectra of 7-acetoxy-6-(2,3-dibromopropyl)-4,8-dimethylcoumarin: determination of ground and excited state dipole moments. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 102, 286–296 (2013)ADSCrossRef Gulseven, Y., Sidir, I.: Solvent effect on the absorption and fluorescence spectra of 7-acetoxy-6-(2,3-dibromopropyl)-4,8-dimethylcoumarin: determination of ground and excited state dipole moments. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 102, 286–296 (2013)ADSCrossRef
Zurück zum Zitat Han, P., Wang, D., Gao, H., Zhang, J., Xing, Y., Yang, Z., Cao, H., He, W.: Third-order nonlinear optical properties of cyanine dyes with click chemistry modification. Dyes Pigm. 149, 8–15 (2018)CrossRef Han, P., Wang, D., Gao, H., Zhang, J., Xing, Y., Yang, Z., Cao, H., He, W.: Third-order nonlinear optical properties of cyanine dyes with click chemistry modification. Dyes Pigm. 149, 8–15 (2018)CrossRef
Zurück zum Zitat Hossain, A., Roy, S., Dolui, B.K.: Effects of thermodynamics on the solvation of amino acids in the pure and binary mixtures of solutions: a review. J. Mol. Liq. 232, 332–350 (2017)CrossRef Hossain, A., Roy, S., Dolui, B.K.: Effects of thermodynamics on the solvation of amino acids in the pure and binary mixtures of solutions: a review. J. Mol. Liq. 232, 332–350 (2017)CrossRef
Zurück zum Zitat Jirasová, J., Bílý, J., Čermáková, L.: The effect of surfactants on the acid-base behavior of methyl red. Part I. A spectrophotometric comparison of the effect of CPB and SDS. Collect. Czech. Chem. Commun. 55, 1491–1499 (1990)CrossRef Jirasová, J., Bílý, J., Čermáková, L.: The effect of surfactants on the acid-base behavior of methyl red. Part I. A spectrophotometric comparison of the effect of CPB and SDS. Collect. Czech. Chem. Commun. 55, 1491–1499 (1990)CrossRef
Zurück zum Zitat Khadem Sadigh, M., Zakerhamidi, M.S., Rezaei, B., Milanchian, K.: Environment effects on the nonlinear absorption properties of Methylene blue under different power of excitation beam. J. Mol. Liq. 229, 548–554 (2017)CrossRef Khadem Sadigh, M., Zakerhamidi, M.S., Rezaei, B., Milanchian, K.: Environment effects on the nonlinear absorption properties of Methylene blue under different power of excitation beam. J. Mol. Liq. 229, 548–554 (2017)CrossRef
Zurück zum Zitat Kulyk, B., Kerasidou, A.P., Soumahoro, L., Moussallem, C., Gohier, F., Frèrea, P., Sahraoui, B.: Optimization and diagnostic of nonlinear optical features of π-conjugated Benzodifuran-based derivatives. RSC Adv. 6, 14439–14447 (2016a)CrossRef Kulyk, B., Kerasidou, A.P., Soumahoro, L., Moussallem, C., Gohier, F., Frèrea, P., Sahraoui, B.: Optimization and diagnostic of nonlinear optical features of π-conjugated Benzodifuran-based derivatives. RSC Adv. 6, 14439–14447 (2016a)CrossRef
Zurück zum Zitat Kulyk, B., Guichaoua, D., Ayadi, A., El-Ghayoury, A., Sahraoui, B.: Metal-induced efficient enhancement of nonlinear optical response in conjugated azo-based iminopyridine complexes. Org. Electron. 36, 1–6 (2016b)CrossRef Kulyk, B., Guichaoua, D., Ayadi, A., El-Ghayoury, A., Sahraoui, B.: Metal-induced efficient enhancement of nonlinear optical response in conjugated azo-based iminopyridine complexes. Org. Electron. 36, 1–6 (2016b)CrossRef
Zurück zum Zitat Kulyk, B., Taboukhat, S., Akdas-Kilig, H., Fillaut, J.-L., Boughalebb, Y., Sahraoui, B.: Nonlinear refraction and absorption activity of dimethylaminostyryl substituted BODIPY dyes. RSC Adv. 6, 84854–84859 (2016c)CrossRef Kulyk, B., Taboukhat, S., Akdas-Kilig, H., Fillaut, J.-L., Boughalebb, Y., Sahraoui, B.: Nonlinear refraction and absorption activity of dimethylaminostyryl substituted BODIPY dyes. RSC Adv. 6, 84854–84859 (2016c)CrossRef
Zurück zum Zitat Larsen, M.C., Perkins, R.J.: Flash photolysis experiment of o-methyl red as a function of pH: a low-cost experiment for the undergraduate physical chemistry lab. J. Chem. Educ. 93(12), 2096–2100 (2016)CrossRef Larsen, M.C., Perkins, R.J.: Flash photolysis experiment of o-methyl red as a function of pH: a low-cost experiment for the undergraduate physical chemistry lab. J. Chem. Educ. 93(12), 2096–2100 (2016)CrossRef
Zurück zum Zitat Lee, M.R., Wang, J.R., Lee, C.R., Fuh, A.: Optically switchable biphotonic photorefractive effect in dye-doped liquid crystal films. Appl. Phys. Lett. 85, 5822–5824 (2005)ADSCrossRef Lee, M.R., Wang, J.R., Lee, C.R., Fuh, A.: Optically switchable biphotonic photorefractive effect in dye-doped liquid crystal films. Appl. Phys. Lett. 85, 5822–5824 (2005)ADSCrossRef
Zurück zum Zitat Lee, S., Wong, J.H., Liu, S.J.: Fluorescence and Raman study of pH effect on the adsorption orientations of methyl red on silver colloids. Appl. Spectrosc. 65, 996–1003 (2011)ADSCrossRef Lee, S., Wong, J.H., Liu, S.J.: Fluorescence and Raman study of pH effect on the adsorption orientations of methyl red on silver colloids. Appl. Spectrosc. 65, 996–1003 (2011)ADSCrossRef
Zurück zum Zitat Li, Q., Chi, Z., Li, T., Ran, X., Guo, L.: Photoresponsive behavior and switchable nonlinear optical properties of Langmuir–Blodgett film based on azobenzene derivatives. Opt. Express 25(10), 11503–11513 (2017a)ADSCrossRef Li, Q., Chi, Z., Li, T., Ran, X., Guo, L.: Photoresponsive behavior and switchable nonlinear optical properties of Langmuir–Blodgett film based on azobenzene derivatives. Opt. Express 25(10), 11503–11513 (2017a)ADSCrossRef
Zurück zum Zitat Li, R., Dong, N., Cheng, C., Ren, F., Hübner, R., Wang, J., Zhou, S., Chen, F.: Giant enhancement of nonlinear optical response in Nd:yAG single crystals by embedded silver nanoparticles. ACS Omega 2(4), 1279–1286 (2017b)CrossRef Li, R., Dong, N., Cheng, C., Ren, F., Hübner, R., Wang, J., Zhou, S., Chen, F.: Giant enhancement of nonlinear optical response in Nd:yAG single crystals by embedded silver nanoparticles. ACS Omega 2(4), 1279–1286 (2017b)CrossRef
Zurück zum Zitat Liaros, N., Couris, S., Maggini, L., De Leo, F., Cattaruzza, F., Aurisicchio, C., Bonifazi, D.: NLO response of photoswitchable azobenzene-based materials. ChemPhysChem 14(13), 2961–2972 (2013)CrossRef Liaros, N., Couris, S., Maggini, L., De Leo, F., Cattaruzza, F., Aurisicchio, C., Bonifazi, D.: NLO response of photoswitchable azobenzene-based materials. ChemPhysChem 14(13), 2961–2972 (2013)CrossRef
Zurück zum Zitat Matazo, D.R.C., Ando, R.A., Borin, A.C., Santos, P.S.: Azo-hydrazone tautomerism in protonated aminoazobenzenes: resonance Raman spectroscopy and quantum-chemical calculations. J. Phys. Chem. A 112, 4437–4443 (2008)CrossRef Matazo, D.R.C., Ando, R.A., Borin, A.C., Santos, P.S.: Azo-hydrazone tautomerism in protonated aminoazobenzenes: resonance Raman spectroscopy and quantum-chemical calculations. J. Phys. Chem. A 112, 4437–4443 (2008)CrossRef
Zurück zum Zitat Mendham, J., Denney, R.C., Barness, J.D.: Quantitative Chemical Analysis, 6th edn. W.H. Freeman, New Delhi (2004) Mendham, J., Denney, R.C., Barness, J.D.: Quantitative Chemical Analysis, 6th edn. W.H. Freeman, New Delhi (2004)
Zurück zum Zitat Motiei, H., Jafari, A., Naderali, R.: Third-order nonlinear optical properties of organic azo dyes by using strength of nonlinearity parameter and Z-scan technique. Opt. Laser Technol. 88, 68–74 (2017)ADSCrossRef Motiei, H., Jafari, A., Naderali, R.: Third-order nonlinear optical properties of organic azo dyes by using strength of nonlinearity parameter and Z-scan technique. Opt. Laser Technol. 88, 68–74 (2017)ADSCrossRef
Zurück zum Zitat Mukherjee, S., Bera, S.C.: Low temperature laser flash photolysis and spectral studies of Methyl Red. J. Chem. Soc. Faraday Trans. 94, 67–71 (1998)CrossRef Mukherjee, S., Bera, S.C.: Low temperature laser flash photolysis and spectral studies of Methyl Red. J. Chem. Soc. Faraday Trans. 94, 67–71 (1998)CrossRef
Zurück zum Zitat Peyghami, S., Sharifi, S., Rakhshanizadeh, F., Alizadeh, K.: Nonlinear optical properties of Rose Bengal: effect of environment. J. Mol. Liq. 246, 157–165 (2017)CrossRef Peyghami, S., Sharifi, S., Rakhshanizadeh, F., Alizadeh, K.: Nonlinear optical properties of Rose Bengal: effect of environment. J. Mol. Liq. 246, 157–165 (2017)CrossRef
Zurück zum Zitat Pourtabrizi, M., Rakhshanizadeh, F., Sharifi, S., Shahtahmasebi, N., Kompany, A.: Effect of l-Alanine concentration on linear and nonlinear optical properties of two dyes in water and nano-confined water. J. Optoelectron. Adv. Mater. 20(5), 302–308 (2018) Pourtabrizi, M., Rakhshanizadeh, F., Sharifi, S., Shahtahmasebi, N., Kompany, A.: Effect of l-Alanine concentration on linear and nonlinear optical properties of two dyes in water and nano-confined water. J. Optoelectron. Adv. Mater. 20(5), 302–308 (2018)
Zurück zum Zitat Sahraoui, B., Rivoire, G.: Degenerate four-wave mixing in absorbing isotropic media. Opt. Commun. 138(1–3), 109–112 (1997)ADS Sahraoui, B., Rivoire, G.: Degenerate four-wave mixing in absorbing isotropic media. Opt. Commun. 138(1–3), 109–112 (1997)ADS
Zurück zum Zitat Saievar Iranizad, E., Dehghani, Z., Nadafan, M.: Nonlinear optical properties of nematic liquid crystal doped with different compositional percentage of synthesis of Fe3O4 nanoparticles. J. Mol. Liq. 190, 6–9 (2014)CrossRef Saievar Iranizad, E., Dehghani, Z., Nadafan, M.: Nonlinear optical properties of nematic liquid crystal doped with different compositional percentage of synthesis of Fe3O4 nanoparticles. J. Mol. Liq. 190, 6–9 (2014)CrossRef
Zurück zum Zitat Sangsefedi, A.S., Sharifi, S., Rezaion, H.R.M.: Fluorescence and nonlinear optical properties of alizarin red S in solvents and droplet. J. Fluorescence 28(3), 815–825 (2018)CrossRef Sangsefedi, A.S., Sharifi, S., Rezaion, H.R.M.: Fluorescence and nonlinear optical properties of alizarin red S in solvents and droplet. J. Fluorescence 28(3), 815–825 (2018)CrossRef
Zurück zum Zitat Schulze, M., Utecht, M., Moldt, T., Przyrembel, D., Gahl, C., Weinelt, M., Saalfrank, P., Tegeder, P.: Nonlinear optical response of photochromic azobenzene-functionalized self-assembled monolayers. Phys. Chem. Chem. Phys. 17, 18079–18086 (2015)CrossRef Schulze, M., Utecht, M., Moldt, T., Przyrembel, D., Gahl, C., Weinelt, M., Saalfrank, P., Tegeder, P.: Nonlinear optical response of photochromic azobenzene-functionalized self-assembled monolayers. Phys. Chem. Chem. Phys. 17, 18079–18086 (2015)CrossRef
Zurück zum Zitat Shavakandi, S.M., Alizadeh, K., Sharifi, S., Marti, O., Amirkhani, M.: Optical study of Xanthene type dyes in nano-confined liquid. J. Phys. D Appl. Phys. 50(15), 155301 (2017)ADSCrossRef Shavakandi, S.M., Alizadeh, K., Sharifi, S., Marti, O., Amirkhani, M.: Optical study of Xanthene type dyes in nano-confined liquid. J. Phys. D Appl. Phys. 50(15), 155301 (2017)ADSCrossRef
Zurück zum Zitat Sindhu Sukumaran, V., Ramanlingam, A.: Spectral characteristics and nonlinear studies of crystal violet dye. A Spectrochim. Acta Part A 63, 673–676 (2006)ADSCrossRef Sindhu Sukumaran, V., Ramanlingam, A.: Spectral characteristics and nonlinear studies of crystal violet dye. A Spectrochim. Acta Part A 63, 673–676 (2006)ADSCrossRef
Zurück zum Zitat Soni, A., Jha, S.K.: A paper strip based non-invasive glucose biosensor for salivary analysis. Biosens. Bioelectron. 67, 763–768 (2015)CrossRef Soni, A., Jha, S.K.: A paper strip based non-invasive glucose biosensor for salivary analysis. Biosens. Bioelectron. 67, 763–768 (2015)CrossRef
Zurück zum Zitat Sousani, A., Moghadam, P.N., Hasanzadeh, R., Motiei, H., Bagheri, M.: Synthesis of polyglycidylmethacrylate grafted azobenzene copolymer: photosensitivity and nonlinear optical properties. Opt. Mater. 51(3–4), 232–240 (2016)ADSCrossRef Sousani, A., Moghadam, P.N., Hasanzadeh, R., Motiei, H., Bagheri, M.: Synthesis of polyglycidylmethacrylate grafted azobenzene copolymer: photosensitivity and nonlinear optical properties. Opt. Mater. 51(3–4), 232–240 (2016)ADSCrossRef
Zurück zum Zitat Vallee, B.L., Gibson, J.G.: An improved dithizone method for the determination of small quantities of zinc in blood and tissue samples. J. Biol. Chem. 176, 435–443 (1948) Vallee, B.L., Gibson, J.G.: An improved dithizone method for the determination of small quantities of zinc in blood and tissue samples. J. Biol. Chem. 176, 435–443 (1948)
Zurück zum Zitat Virkki, M., Tuominen, O., Kauranen, M., Priimagi, A.: Photoinduced nonlinear optical response in azobenzene-functionalized molecular glass. Opt. Express 24(5), 4964–4971 (2016)ADSCrossRef Virkki, M., Tuominen, O., Kauranen, M., Priimagi, A.: Photoinduced nonlinear optical response in azobenzene-functionalized molecular glass. Opt. Express 24(5), 4964–4971 (2016)ADSCrossRef
Zurück zum Zitat YassinAl-Ahmad, A., Hassan, Q.M.A., AliBadran, H., Ali Hussain, K.: Investigating some linear and nonlinear optical properties of the azo dye. Opt. Laser Technol. 44, 1450–1455 (2012)ADSCrossRef YassinAl-Ahmad, A., Hassan, Q.M.A., AliBadran, H., Ali Hussain, K.: Investigating some linear and nonlinear optical properties of the azo dye. Opt. Laser Technol. 44, 1450–1455 (2012)ADSCrossRef
Zurück zum Zitat Zawadzka, A., Płóciennik, P., Strzelecki, J., Pranaitis, M., Dabos-Seignon, S., Sahraoui, B.: Structural and nonlinear optical properties of as-grown and annealed metallophthalocyanine thin films. Thin Solid Films 545, 429–437 (2013)ADSCrossRef Zawadzka, A., Płóciennik, P., Strzelecki, J., Pranaitis, M., Dabos-Seignon, S., Sahraoui, B.: Structural and nonlinear optical properties of as-grown and annealed metallophthalocyanine thin films. Thin Solid Films 545, 429–437 (2013)ADSCrossRef
Zurück zum Zitat Zheng, Y., Ye, Q., Wang, C., Wang, J., Deng, Z., Mei, J., Zhou, W., Zhang, C., Tian, J.: Nonlinear optical properties of methyl red under CW irradiation. Opt. Laser Technol. 75, 132–137 (2015)ADSCrossRef Zheng, Y., Ye, Q., Wang, C., Wang, J., Deng, Z., Mei, J., Zhou, W., Zhang, C., Tian, J.: Nonlinear optical properties of methyl red under CW irradiation. Opt. Laser Technol. 75, 132–137 (2015)ADSCrossRef
Metadaten
Titel
Impact of amino acids, organic solvents and surfactants on azo-hydrazone tautomerism in Methyl Red: spectral-luminescent and nonlinear optical properties
verfasst von
Soheil Sharifi
Muhammad Faizan Nazar
Forough Rakhshanizadeh
Seyed Ahmad Sangsefedi
Afshin Azarpour
Publikationsdatum
01.02.2020
Verlag
Springer US
Erschienen in
Optical and Quantum Electronics / Ausgabe 2/2020
Print ISSN: 0306-8919
Elektronische ISSN: 1572-817X
DOI
https://doi.org/10.1007/s11082-020-2211-3

Weitere Artikel der Ausgabe 2/2020

Optical and Quantum Electronics 2/2020 Zur Ausgabe

Neuer Inhalt