Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Solvent Effects on the Solvatochromism of 7-Aminocoumarin Derivatives in Neat and Binary Solvent Mixtures: Correlation of the Electronic Transition Energies with the Solvent Polarity Parameters

  • Published : 2009.07.20
Download PDF
⟨ Previous Next ⟩

Abstract

The change in the electronic absorption and emission energy of 7-aminocoumarin derivatives in binary solvent mixtures has been studied. The electronic transition energy along with the Stokes' shift is correlated with the orientation polarizability of the solvent as well as the empirical solvent polarity parameters $E_T$ (30). It is observed that the emission peak shift traces the change of $E_T$ (30) value very closely in binary solvent mixtures. The emission transition more strongly depends on the solvent polarity than the absorption, which indicates the dipole moment gets larger on excitation. From the dependence of the Stokes’ shift of 7-aminocoumarins with the solvent polarity parameters and the ground state dipole moment obtained by the semi-empirical calculations, the excited state dipole moment was estimated. The fluorescence lifetime change of 7-aminocoumarins in binary solvent mixtures was measured and the results are explained in terms of molecular conformation and solvent polarity. The study indicates the empirical solvent polarity $E_T$ (30) is a good measure of microscopic solvent polarity and it probes in general the non-specific solvent interactions.

Keywords

References

  1. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 3rd ed.; VCH: 2004
  2. Gordon, D. J.; Balbach, J. J.; Tycko, R.; Meredith, S. C. Biophys. J. 2004, 86, 428 https://doi.org/10.1016/S0006-3495(04)74119-3
  3. Prusiner, S. B. Proc. Natl. Acad. Sci. USA 1998, 95, 13363 https://doi.org/10.1073/pnas.95.23.13363
  4. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486 https://doi.org/10.1021/ja01299a050
  5. Kirkwood, J. G. J. Chem. Phys. 1934, 2, 351 https://doi.org/10.1063/1.1749489
  6. Kosower, E. M. J. Am. Chem. Soc. 1958, 80, 3253 https://doi.org/10.1021/ja01546a020
  7. Kosower, E. M.; Mohammad, M. J. Phys. Chem. 1970, 74, 1153 https://doi.org/10.1021/j100700a037
  8. Dimroth, K.; Reichardt, C.; Siepmann, T.; Bohlmann, F. Liebigs Ann. Chem. 1963, 661, 1 https://doi.org/10.1002/jlac.19636610102
  9. Reichardt, C. Liebigs Ann. Chem. 1971, 752, 64 https://doi.org/10.1002/jlac.19717520109
  10. Plieninger, P.; Baumgartel, H. Ber. Bunsenges. Phys. Chem. 1982, 96, 161
  11. Zachariasse, K. A.; Van Phuc, N.; Kozankiewicz, B. J. Phys. Chem. 1981, 85, 2676 https://doi.org/10.1021/j150618a022
  12. Johnson, B. P.; Khaledi, M. G.; Dorsey, J. G. J. Chromatogr. 1987, 384, 221 https://doi.org/10.1016/S0021-9673(01)94673-4
  13. Von Lippert, E. Z. Electrochem. 1957, 61, 962
  14. Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem., Soc. Jpn. 1956, 29, 465 https://doi.org/10.1246/bcsj.29.465
  15. Langhals, H. Angew. Chem. Int. Engl. 1982, 21, 724 https://doi.org/10.1002/anie.198207241
  16. Kawski, A. Progress in Photochemistry and Photophysics Vol. V; Rabek, J. F., Ed.; CRC press: 1992
  17. Ravi, M; Soujanya, T.; Samanta, A.; Radhakrishnan, T. P. J. Chem. Soc. Faraday Trans. 1995, 91, 2739 https://doi.org/10.1039/ft9959102739
  18. Mannekutla, J. R.; Mulimani, B. G.; Inamdar, S. R. Spectrochim. Acta Part A 2008, 69, 419 https://doi.org/10.1016/j.saa.2007.04.016
  19. Raikar, U. S.; Renuka, C. G.; Nadaf, Y. F.; Mulimani, B. G.; Karguppikar, A. M.; Soudagar, M. K. Spectrochim. Acta Part A 2006, 65, 673 https://doi.org/10.1016/j.saa.2005.12.028
  20. Lewis, J. E.; Maroncelli, M. Chem. Phys. Lett. 1998, 282, 197 https://doi.org/10.1016/S0009-2614(97)01270-0
  21. Jones II, G.; Jackson, W. R.; Choi, C. Y.; Bergmark, W. R. J. Phys. Chem. 1985, 89, 294 https://doi.org/10.1021/j100248a024
  22. Barik, A.; Kumbhakar, M.; Nath, S.; Pal, H. Chem. Phys. 2005, 315, 277 https://doi.org/10.1016/j.chemphys.2005.04.018
  23. Dahiya, P.; Kumbhakar, M.; Mukherjee, T.; Pal, H. Chem. Phys. Lett. 2005, 414, 148 https://doi.org/10.1016/j.cplett.2005.08.051
  24. Chu, G.; Yangbo, F. J. Chem. Soc., Faraday Trans. I 1987, 83, 2533 https://doi.org/10.1039/f19878302533
  25. Berezin, M. Y.; Lee, H.; Akers, W.; Achilefu, S. Biophys. J. 2007, 93, 2892 https://doi.org/10.1529/biophysj.107.111609

Cited by

  1. A broad spectrum dark quencher: construction of multiple colour protease and photolytic sensors vol.49, pp.60, 2013, https://doi.org/10.1039/c3cc42628a
  2. Surface Functionalization of Nanoparticles with Polyethylene Glycol: Effects on Protein Adsorption and Cellular Uptake vol.9, pp.7, 2015, https://doi.org/10.1021/acsnano.5b01326
  3. Microwave Assisted Synthesis, Optical Properties and Physicochemical Investigations on the Powerful Fluorophore: Donor (D) -π-Acceptor (A) Chalcone vol.26, pp.6, 2016, https://doi.org/10.1007/s10895-016-1909-x
  4. Solvatochromic effect and kinetics of methyl violet reduction with potassium iodide in water–isopropanol mixtures vol.90, pp.13, 2016, https://doi.org/10.1134/S0036024416130136
  5. Spectroscopic Physicochemical and Photophysical Investigation of Biologically Active 2-oxo-quinoline-3-carbonitrile Derivative vol.27, pp.3, 2017, https://doi.org/10.1007/s10895-016-2021-y
  6. Green Synthesis, Spectrofluorometric Characterization and Antibacterial Activity of Heterocyclic Compound from Chalcone on the Basis of in Vitro and Quantum Chemistry Calculation vol.27, pp.3, 2017, https://doi.org/10.1007/s10895-017-2028-z
  7. Dual Fluorescence and Solvatochromic Study on 3-Acyl Coumarins vol.27, pp.4, 2017, https://doi.org/10.1007/s10895-017-2052-z
  8. Mixed Solvent Chemistry through Synergistic Solvation: Structure, Property and Function of t-Butanol—Dichloromethane Binary Solvent Mixtures vol.46, pp.2, 2017, https://doi.org/10.1007/s10953-017-0586-y
  9. Analytical micelles containing amphiphilic aminoanthraquinone solvatochromic reporter receptor vol.79, pp.6, 2017, https://doi.org/10.1134/S1061933X17060060
  10. Structural, vibrational, electronic, NMR and reactivity analyses of 2-amino-4H-chromene-3-carbonitrile (ACC) by ab initio HF and DFT calculations vol.89, pp.None, 2009, https://doi.org/10.1016/j.saa.2011.12.050
  11. Effects of the solvent polarity of a polymeric insulator on field-effect mobility in an organic thin-film transistor vol.81, pp.None, 2013, https://doi.org/10.1016/j.sse.2012.12.014
  12. Determination of Excited Singlet-State Dipole Moments of Methoxy and Dimethylamino Substituted Benzylidenebenzosuberones Using Solvatochromic Method vol.48, pp.5, 2009, https://doi.org/10.1080/00387010.2014.881378
  13. Investigating the molecular and aggregated states of a drug molecule rutaecarpine using spectroscopy, microscopy, crystallography and computational studies vol.17, pp.21, 2009, https://doi.org/10.1039/c5cp01980j