Skip to main content
SpringerLink
Log in

Fluorescence Spectral Properties of Methyl Orange in Homogeneous Media

  • Original Article
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

The methyl orange [C14H14N3SO3Na], an azo dye exhibited strong emission and large Stokes shift in various solvents, and the largest shift (Δλ = 125.51nm or Δν = 9297cm-1) was obtained in the water. The UV-visible spectra of the dye showed the absorption in the range (33,333 – 20,000) cm-1. We found that solvent effects on the absorption wavelength are consistent. The bathochromic shift in water and the hypsochromic shift in methanol observed in the absorption (43 nm) as well as in the fluorescence (42 nm) spectra predict the strong solute-solvent interaction. The fluorescence quantum yield (ɸf) was decreased from 24% in DMSO to 5% in water. The fluorescent properties of this dye are strongly solvent dependent, the wavelength of minimum fluorescence emission (λem = 435.51nm) shifts to the red. The maximum and minimum calculated oscillator strength is 32% with (Ɛmax = 29011 M-1cm-1) and 11% (Ɛmax = 6682 M-1cm-1) in methanol and DMSO, respectively. Protonated solvents without exception give a shorter lifetime and lower quantum yield. The average excited-state lifetime of the dye was found maximum (τav = 5.36 ns) in DMSO. Also, fluorescence lifetime was combined to deduce the radiative and non-radiative decay rate.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Griffiths J (1988) Specialty dyes-trends in modern chemistry. J Soc Dyers Color 104(11):416–424. https://doi.org/10.1111/j.1478-4408.1988.tb01139.x

    Article  CAS  Google Scholar 

  2. De Martino S, Mauro F, Netti PA (2020) Photonic applications of azobenzene molecules embedded in amorphous polymer. Riv Nuovo Cim 43:599–629. https://doi.org/10.1007/s40766-021-00014-x

    Article  CAS  Google Scholar 

  3. Yonggang Liu Y, Chen B, Zhao J, Liu Q (2020) Photosensitizer PCBM tuning of azo dyes-based composites: Third-order nonlinear optical properties. Opt Mater 108:110187. https://doi.org/10.1016/j.optmat.2020.110187

    Article  CAS  Google Scholar 

  4. Chang TC, Lin JJ, Lin KC et al (2002) Investigation of DNA–protein recognition by satellite hole spectra of labeling dye. J Lumin 98:149–152. https://doi.org/10.1016/S0022-2313(02)00263-6

    Article  CAS  Google Scholar 

  5. Bertolino CA, Caputo G, Barolo C et al (2006) Novel heptamethine cyanine dyes with large stokes’ shift for biological applications in the near infrared. J Fluor 16:221–225. https://doi.org/10.1007/s10895-006-0094-8

    Article  Google Scholar 

  6. Sutter M, Oliveira S, Sanders NN (2007) J Fluor 17: 181–192. Sensitive spectroscopic detection of large and denatured protein aggregates in solution by use of the fluorescent dye Nile red. J Fluor 17:181–192. https://doi.org/10.1007/s10895-007-0156-6

    Article  CAS  Google Scholar 

  7. Hyeyoung P, Eung-Ryul K, Jin KD, Haiwon L (2002) Synthesis of metal-azo dyes and their optical and thermal properties as recording materials for DVD-R. Bull Chem Soc Jpn 75:2067–2070. https://doi.org/10.1246/bcsj.75.2067

    Article  Google Scholar 

  8. Gao T, Xue Y, Zhang Z, Que W (2018) Multi-wavelength optical data processing and recording based on azo-dyes doped organic-inorganic hybrid film. Opt Express 26:4309–4317. https://doi.org/10.1364/OE.26.004309

    Article  PubMed  CAS  Google Scholar 

  9. Samanta S, Beharry AA, Sadovski O, McCormick TM, Babalhavaeji A, Tropepe V, Woolley GA (2013) Photoswitching azo compounds in vivo with red light. J Am Chem Soc 135:9777–9784. https://pubs.acs.org/ https://doi.org/10.1021/ja402220t

  10. Soreño ZV, Puguan JMC, Kim H (2020) Thermochromic transition analysis of elastomer prepared from azo dye-siloxane blend. Mater Chem Phys 240:122297–122304. https://doi.org/10.1016/j.matchemphys.2019.122297

    Article  CAS  Google Scholar 

  11. Saeed A, Shabir G (2014) Synthesis, characterization and fluorescence studies of novel tetrachloroperylene-azo hybrid dyes. J Fluor 24:1337–1345. https://doi.org/10.1007/s10895-014-1420-1

    Article  CAS  Google Scholar 

  12. Gromova YA, Orlova AO, Maslov VG, Fedorov AV, Baranov AV (2013) Fluorescence energy transfer in quantum dot/azo dye complexes in polymer track membranes. Nano Res Lett 8:452–457. https://doi.org/10.1186/1556-276X-8-452

    Article  CAS  Google Scholar 

  13. Ferreira GR, Marcial BL, Garcia HC, Faulstich FRL, Dos Santos HF, de Oliveira LFC (2015) Supramolecular compounds of azo dyes derived from 1-phenylazo-2-naphthol and their nickel and copper complexes. Supramol Chem 27:13–20. https://doi.org/10.1080/10610278.2014.899598

    Article  CAS  Google Scholar 

  14. Schab-Balcerzak E, Konieczkowska J, Siwy M, Sobolewska A, Wojtowicz M, Wiacek M (2014) Comparative studies of polyimides with covalently bonded azo-dyes with their supramolecular analoges: Thermo-optical and photoinduced properties. Opt Mater 36:892–902. https://doi.org/10.1016/j.optmat.2013.12.017

    Article  CAS  Google Scholar 

  15. Matharu AS, Jeeva Sh, Huddleston PR, Ramanujam PS (2007) Synthesis and optical storage properties of a thiophene-based holographic recording medium. J Mater Chem 17:4477–4482. https://doi.org/10.1039/B705648F

    Article  CAS  Google Scholar 

  16. Dinçalp H, Toker F, Durucasu I, Avcibasi N, Icli S (2007) New thiophene-based azo ligands containing azo methine group in the main chain for the determination of copper (II) ions. Dyes Pigm 75:11–24. https://doi.org/10.1016/j.dyepig.2006.05.015

    Article  CAS  Google Scholar 

  17. Chudgar RJ, Oakes J (2003) Azo, Dyes. Kirk-Othmer Encycl of Chem Tech. John Wiley & Sons Inc. https://doi.org/10.1002/0471238961.01261503082104.a01.pub2

    Article  Google Scholar 

  18. Bisht B, Pant S, Giri M (2021) Static and dynamic fluorescence spectroscopic analyses of direct yellow 27—an azo dye. Indian J Phys. https://doi.org/10.1007/s12648-021-02040-1

    Article  Google Scholar 

  19. Rezaei-Seresht E, Salimi A, Mahdavi B (2019) Synthesis, antioxidant and antibacterial activity of azo dye-stilbene hybrid compounds. Pigm Resin Technol 48:84–88. https://doi.org/10.1108/PRT-01-2018-0005

    Article  CAS  Google Scholar 

  20. Ali Y, Hamid SA, Rashid U (2018) Biomedical applications of aromatic azo compounds. Mini Rev Med Chem 18:1548–1558. https://doi.org/10.2174/1389557518666180524113111

    Article  PubMed  CAS  Google Scholar 

  21. Homocianu M, Anton A, Dana OD (2011) Solvent effects on the electronic absorption and fluorescence spectra. J Adv Res Phys 2(1):011105. https://citeseerx.ist.psu.edu/viewdoc

  22. Airinei A, Homocianu M, Dorohoi DO (2010) Changes induced by solvent polarity in electronic absorption spectra of some azo disperse dyes. J Mol Liq 157:13–17. https://doi.org/10.1016/j.molliq.2010.07.011

    Article  CAS  Google Scholar 

  23. Suppan P, Ghoneim N (1997) Solvatochromism. Royal Society of Chemistry, Cambridge

    Google Scholar 

  24. Jayabharathi J, Thanikachalam V, Perumal MV, Jayamoorthy K (2012) Solvatochromic Studies of Fluorescent Azo Dyes: Kamlet-Taft (π*, α and β) and Catalan (Spp, SA and SB) Solvent Scales Approach. J Fluoresc 22:213–221. https://doi.org/10.1007/s10895-011-0948-6

    Article  PubMed  CAS  Google Scholar 

  25. Reichardt C (1994) Solvatochromic dyes as solvent polarity indicators. Chem Rev 94:2319–2358. https://doi.org/10.1021/cr00032a005

    Article  CAS  Google Scholar 

  26. Reichardt C (2005) Polarity of ionic liquids determined empirically by means of solvatochromicpyridinium N-phenolate betaine dyes. Green Chem 7:339–351. https://doi.org/10.1039/B500106B

    Article  CAS  Google Scholar 

  27. Green FJ (1990) The Sigma Aldrich Handbook of Stains, Dyes and Indicators. Aldrich Chemical Co., Inc., Milwaukee

    Google Scholar 

  28. Bhankhar A, Giri M, Jaggi Yadav K, N, (2014) Study on degradation of methyl orange-an azo dye by silver nanoparticles using UV–Visible spectroscopy. Indian J Phys 88:1191–1196. https://doi.org/10.1007/s12648-014-0555-x

    Article  CAS  Google Scholar 

  29. Lakowicz JR (2006) Principles of fluorescence spectroscopy, 3rd ed. Springer, US. https://doi.org/10.1007/978-0-387-46312-4

  30. Zhu G, Fang H, Xiao Y, Hursthouse AS (2020) The application of fluorescence spectroscopy for the investigation of dye degradation by chemical oxidation. J Fluor 30:1271–1279. https://doi.org/10.1007/s10895-020-02591-2

    Article  CAS  Google Scholar 

  31. Li J, Wu N (2017) Biosensors Based on Nanomaterials and Nanodevices. CRC Press. https://doi.org/10.1201/b16234

    Article  Google Scholar 

  32. Williams ATR, Winfield SA, Miller JN (1983) Relative fluorescence quantum yields using a computer-controlled luminescence spectrometer. Analyst 108:1067–1071. https://doi.org/10.1039/AN9830801067

    Article  CAS  Google Scholar 

  33. Brandner B (2016) Implementation of a comparative method for measuring photoluminescence quantum yields of novel compounds in solution. Oregon State University. https://ir.library.oregonstate.edu/concern/undergraduate_thesis_or_projects/8336h352

  34. Asiri AM, Sobahi TR, Osman OI, Khan SA (2017) Photophysical investigation of (Dp-A) DMHP dye: dipole moments, photochemical quantum yield and fluorescence quantum yield, by solvatochromic shift methods and DFT studies. J Mol Struct 1128:636–644. https://doi.org/10.1016/j.molstruc.2016.08.081

    Article  CAS  Google Scholar 

  35. Bani-Yaseen AD, Hammad F, Ghanem BS, Mohammad EG (2013) On the photophysicochemical properties of selected fluoroquinolones: solvatochromic and fluorescence spectroscopy study. J Fluor 23:93–101. https://doi.org/10.1007/s10895-012-1120-7

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to Prof. R. P. Singh, School of Life Sciences, Jawaharlal Nehru University (JNU) for his guidance and laboratory facilities. Thanks are due to Dr. Sobhan Sen, School of Physical Sciences, JNU for many stimulating discussions and providing the facility of steady-state measurements.

Funding

The authors did not receive support from any organization for the submitted work and have no relevant financial or non-financial interests to disclose.

Author information

Authors and Affiliations

  1. Photophysics Laboratory, Department of Physics, Centre of Advanced Study, D.S.B. Campus, Kumaun University, Uttarakhand, 263 002, Nainital, India

    Babita Bisht & Sanjay Pant

  2. Department of Physics, Jagdish Saran Hindu (PG) College, Amroha, Mahatma Jyotiba Phule, Rohilkhand University, Uttar Pradesh, 243 006, Bareilly, India

    Priyank Bhardwaj

  3. Department of Physics, Sri Venkateswara College, University of Delhi, Benito Juarez Road, 110 021, New Delhi (Delhi), India

    Manoj Giri

Authors
  1. Babita Bisht
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Priyank Bhardwaj
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Manoj Giri
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sanjay Pant
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

These authors contributed equally. Babita Bisht: Performed steady-state and lifetime spectroscopic measurements, written-original draft and, did formal analysis. Priyank Bhardwaj: Formal analysis, sample preparation. Manoj Giri: Validation, Writing - review & editing, analysis. Sanjay Pant: Initiated the idea and supervised the work. All authors contributed to the analysis of experimental results and completing the manuscript.

Corresponding authors

Correspondence to Manoj Giri or Sanjay Pant.

Ethics declarations

Ethics Approval

Not applicable.

Consent to Participate

Not applicable.

Consent for Publication

Not applicable.

Conflicts of interests/Competing interests

The authors have no conflicts of interest/competing interests.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bisht, B., Bhardwaj, P., Giri, M. et al. Fluorescence Spectral Properties of Methyl Orange in Homogeneous Media. J Fluoresc 31, 1787–1795 (2021). https://doi.org/10.1007/s10895-021-02820-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-021-02820-2

Keywords

Search

Navigation