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Spectroscopic, Photophysical Investigation and Micellization for Critical Micelle Concentration of 3-(3,4-Dimethoxyphenyl)-1-(2,5-Dimethylfuran-3-Yl)Prop-2-En-1-One Dye

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Journal of Applied Spectroscopy Aims and scope

3-(3,4-Dimethoxyphenyl)-1-(2,5-dimethylfuran-3-yl)prop-2-en-1-one (DDFP) was prepared by the reaction of 3-acetyl-2,5-dimethylfuran and 3,4-dimethoxybenzaldehyde. Data obtained from FT-IR, 1H-NMR, 13C-NMR, EIMS, and elemental analysis were consistent with the chemical structure of the newly prepared DDFP. Electronic absorption and emission spectrum of DDFP have been measured in different solvents. DDFP dye exhibits red shift in emission spectrum as solvent polarity increases, indicating a large change in dipole moment of DDFP molecule upon excitation due to intramolecular charge transfer in excited DDFP. Excited state intermolecular hydrogen bonding affects the energy of emission spectrum and fluorescence quantum yield of DDFP molecule. DDFP dye undergoes solubilization in different micelles and may be used as a probe or quencher to determine the critical micelle concentration (CMC) of CTAB and SDS. The pho to reactivity and net photochemical quantum yield (φc) of DDFP are determined in solvents CHCl3, CH2Cl2, CCl4, and DMSO. The dye is relatively photostable in DMSO and displays photodecomposition in chloromethane solvents.

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References

  1. S. Syam, S. I. Abdelwahab, M. A. Al-Mamary, and S. Mohan, Molecules, 17, 6179–6195 (2012).

    Article  Google Scholar 

  2. B Ngameni, J. Watchueng, F. F. Boyom, F. Keumedjio, B. T. Ngadjui, J. Gut, B. M. Abegaz, and P. J. Rosenthal, Arkivoc, xiii, 116–123 (2007).

    Google Scholar 

  3. V. Banewar, J. Chem., 2013, ID 542973, 4–9 (2013).

    Google Scholar 

  4. S. Won, C. Liu, L. Tsao, J. Weng, H. Ko, J. Wang, and C. Lin, Eur. J. Med. Chem., 40, 103–112 (2005).

    Article  Google Scholar 

  5. H. Sharma, S. Patil, T. W. Sanchez, N. Neamati, R. F. Schinazi, and J. K. Buolamwini, Bioorg. Med. Chem., 19, 2030–2045 (2011).

    Article  Google Scholar 

  6. G. S. B. Viana, M. A. M. Bandeira, and F. J. A. Matos, Phytomedicine, 10, 189–195 (2003).

    Article  Google Scholar 

  7. E. M. Ebeid, M. H. Abdel-Kader, R. M. Issa, and S. A. El-Daly, Chem. Phys. Lett., 146, 331–336 (1988).

    Article  ADS  Google Scholar 

  8. R. Prasath, P. Bhavana, S. W. Ng, and E. R. T. Tiekink, J. Organomet. Chem., 726, 62–70 (2001).

    Article  Google Scholar 

  9. M. Matsuoka, M. Furushow, S. Iida, and T. Kitao, Nonlinear Opt., 231–236 (1992).

  10. A. Ghouili, M. Dusek, V. Petricek, T. B. Ayed, and R. B. Hassen, J. Phys. Chem., 75, 88–193 (2014).

    Google Scholar 

  11. P. Poornesh, S. Shettigar, G. Umesh, K. B. Manjunatha, K. P. Kamath, B. K. Sarojini, and B. Naraya, Opt. Mater., 31, 854–859 (2009).

    Article  ADS  Google Scholar 

  12. Y. F. Sun, S. Xu, R. Wu, Z. Wang, Z. Zheng, J. Li, and Y. Cui, Dyes Pigments, 87, 109–118 (2010).

    Article  Google Scholar 

  13. M. Gaber, S. A. El-Daly, T. A. Fayed, and Y. S. El-Sayed, Opt. Laser Technol., 40, 528–537 (2008).

    Article  ADS  Google Scholar 

  14. G. J. Pant, P. Singh, B. S. Rawat, M. S. M. Rawat, and G. C. Joshi, Spectrochim. Acta A, 78, 1075–1079 (2011).

    Article  ADS  Google Scholar 

  15. H. M. Marwani, A. M. Asiri, and S. A. Khan, J. Lumin., 136, 296–302 (2013).

    Article  Google Scholar 

  16. Y. Yesuthangam, S. Pandian, K. Venkatesan, R. Gandhidasan, and R. Murugesan, Photochem. Photobiol. B, 102, 200–208 (2011).

    Article  Google Scholar 

  17. S. El-Daly, A. M. Asiri, S. A. Khan, and K. A. Alamry, J. Lumin., 134, 819–824 (2013).

    Article  Google Scholar 

  18. R. Frolicker, J. Phys. Chem. A, 106, 1708–1722 (2002).

    Article  Google Scholar 

  19. S. Suppan, J. Photochem. Photobiol. A: Chem., 50, 293–297 (1990).

    Article  Google Scholar 

  20. N. Mataga, T. Kubota, Molecular Interaction and Electronic Spectra, Marcel Dekker, New York (1970).

    Google Scholar 

  21. M. Gaber, S. A. El-Daly, T. A. Fayed, and Y. S. El-Sayed, Opt. Laser Technol., 40, 528–537 (2008).

    Article  ADS  Google Scholar 

  22. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 12nd ed., VCH, Weiheim, 35, 359 (1988).

  23. K. Rurack, M. L. Dekhtyar, J. L. Bricks, U. Resch-Genger, and W. Retting, J. Phys. Chem. A, 103, 9626–9635 (1999).

    Article  Google Scholar 

  24. R. Gahlaut, N. Tewari, J. P. Bridhkoti, N. K. Joshi, H. C. Joshi, and S. Pant, J. Mol. Liq., 161, 141–146 (2011).

    Article  Google Scholar 

  25. S. A. El-Daly, A. M. Asiri, K. A. Alamry, and A. Y. Obaid, J. Lumin., 139, 69–78 (2013).

    Article  Google Scholar 

  26. K. N. Ganesh, P. Mitra, and D. Balasubramanian, J. Phys. Chem., 86, 4291–4298 (1982).

    Article  Google Scholar 

  27. K. A. Dill, D. E. Koppel, R. S. Cantor, J. D. Dill, D. Bendouch, and S. H. Chen, Nature, 309, 42–45 (1984).

    Article  ADS  Google Scholar 

  28. M. C. Biondic and R. Erra-Balsells, Photochem. Photobiol. A, 77, 149–159 (1994).

    Article  Google Scholar 

  29. M. C. Biondic and R. Erra-Balsells, Photochem. Photobiol. A, 51, 341–353 (1990).

    Article  Google Scholar 

Download references

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Authors and Affiliations

  1. King Abdulaziz University, Chemistry Department, Faculty of Science, P.O. Box 80203, Jeddah, 21589, Saudi Arabia

    S. A. Khan & A. M. Asiri

  2. Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, Saudi Arabia

    A. M. Asiri

Authors
  1. S. A. Khan
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  2. A. M. Asiri
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Correspondence to S. A. Khan.

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Abstract of article is published in Zhurnal Prikladnoi Spektroskopii, Vol. 84, No. 4, p. 668, July–August, 2017.

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Khan, S.A., Asiri, A.M. Spectroscopic, Photophysical Investigation and Micellization for Critical Micelle Concentration of 3-(3,4-Dimethoxyphenyl)-1-(2,5-Dimethylfuran-3-Yl)Prop-2-En-1-One Dye. J Appl Spectrosc 84, 687–693 (2017). https://doi.org/10.1007/s10812-017-0531-2

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  • DOI: https://doi.org/10.1007/s10812-017-0531-2

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