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

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Abstract

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.

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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

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Key words

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