Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Synthesis and characterization of a solvatochromic, lipophilic fluorescent oxazone: 1-Pentyl-7-dimethylamino-3H-phenoxazine-3-one

  • 78 Accesses

  • 3 Citations


Olivetol and 4-nitroso-N,N-dimethylaniline were combined under reflux in acetic acid to produce 1-pentyl-7-dimethylamino-3H-phenoxazine-3-one (1-PDMPO). The fluorescent behavior of the purified compound in a variety of solutions and samples was investigated. Excitation and emission spectra in pure solvents and mixtures of solvents demonstrate solvatochromism, indicating that the fluorescence response of this compound is affected by its environment. Nonpolar, aprotic solvents as well as protic, polar solvents diminish fluorescent emission in the spectral regions examined, and trends in the fluorescence decary lifetimes measured in five pure solvents are consistent with these intensity changes. The anisotropy excitation spectrum taken in glycerol for 1-PDMPO at −15°C appears to be consistent with the presence of a single electronic state upon excitation, with anisotropy values approaching 0.35 over 400–600 nm. Fluorescence emission is also diminished at low acid concentrations in methanol, with smaller decreases observed in more highly concentrated basic solutions. Emission peaks in aqueous sodium dodecyl sulfate solutions, extruded egg phosphatidylcholine vesicles, and fatty acid free bovine serum albumin suspensions all lie above 600 nm, with emission in the albumin suspension displaying a broad shoulder extending to 800 nm. The fluorescent properties of this compound suggest that it or structural homologues may have utility as fluorescent biological probes.

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


  1. 1.

    I. Johnson (1992) in R. P. Haugland (Ed.),Molecular Probes Handbook of Fluorescent Probes and Research Chemicals, Molecular Probes, Eugene, OR, pp. 1–3.

  2. 2.

    J. N. Miller, M. B. Brown, N. J. Seare, and S. Summerfield (1993) in O. S. Wolfbeis (Ed.),Fluorescence Spectroscopy — New Methods and Applications, Springer-Verlag, Berlin, pp. 189–196.

  3. 3.

    J. R. Lakowicz, M. L. Johnson, W. J. Lederer, H. Szmacinski, K. Nowaczyk, H. Malak, and K. Berndt (1992)Laser Focus World 28, 60–62 66, 68, 77–78.

  4. 4.

    S. Grenci (1983)Fluorescence Efficiencies of Several Cyclized Azo-Merocyanine Dyes, Ph.D. thesis, Rutgers University, New Brunswick, NJ (Univ. Microfilms. Int. 8406369).

  5. 5.

    D. L. Sackett and J. Wolff (1987)Anal. Biochem. 167, 228–234.

  6. 6.

    V. Dostal, M. Martinek, and E. Ruzicka (1975)Acta Univ. Palackianae Olumucensis — Facultas Rerum Natural. 41, 105–110.

  7. 7.

    M. J. Hope, M. B. Bally, g. Webb, and P. R. Cullis (1985)Biochim. Biophys. Acta 812, 55–65.

  8. 8.

    W. Shaver, C. Golini, and B. W. Williams, unpublished observations.

  9. 9.

    G. Dutt, S. Doriaswamy, N. Periasamy, and B. Venkataraman (1990)J. Chem. Phys. 93, 8498–8513.

  10. 10.

    R. D. Lille (1977)H. J. Conn's Biological Stains (9th ed.), Williams and Wilkins, Baltimore, p. 397.

  11. 11.

    J. R. Daban, M. Sanso, and S. Bartolome (1991)Anal. Biochem. 199, 162–168.

  12. 12.

    K. Goodling, K. Johnson, L. Lefkowitz, and B. W. Williams (1993)J. Chem. Ed. (in press).

  13. 13.

    D. L. Sackett, J. R. Knutson, and J. Wolff (1990)J. Biol. Chem. 265, 14899–14906.

  14. 14.

    E. Petrochenko, A. Gorelenko, N. Alekseev, and A. Akhrem (1991)Dokl. Akad. Nauk BSSR 35, 918–922. (An English translation of this article is available upon request).

  15. 15.

    J. Riddick, W. Bunger, and T. Sakano (1986)Organic Solvents, 4th ed., J. Wiley & Sons, New York.

Download references

Author information

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Brugel, T.A., Williams, B.W. Synthesis and characterization of a solvatochromic, lipophilic fluorescent oxazone: 1-Pentyl-7-dimethylamino-3H-phenoxazine-3-one. J Fluoresc 3, 69–76 (1993). https://doi.org/10.1007/BF00865320

Download citation

Key words

  • 1-Pentyl-7-dimethylamino-3H-phenoxazine-3-one
  • fluorescent oxazone
  • solvatochromism