Fluorescence properties of methyl 8-(2-anthroyl) octanoate, a solvatochromic lipophilic probe
| Autor: | Etienne Perochon, Jean-François Tocanne, André Lopez |
|---|---|
| Rok vydání: | 1991 |
| Předmět: |
Molecular Structure
Chemistry Hydrogen bond Organic Chemistry Solvatochromism Fluorescence spectrometry Quantum yield Membranes Artificial Cell Biology Chromophore Photochemistry Biochemistry Fluorescence Solvent Spectrometry Fluorescence Solvents Indicators and Reagents Solvent effects Caprylates Molecular Biology |
| Zdroj: | Chemistry and physics of lipids. 59(1) |
| ISSN: | 0009-3084 |
| Popis: | Fluorescence excitation and emission spectra, relative fluorescence quantum yield φ r and fluorescence lifetime τ of methyl 8-(2-anthroyl)-octanoate have been studied in a set of organic solvents covering a large scale of polarity and in the presence of water. In this probe, the 2-anthroyl chromophore exhibits quite remarkable and unique fluorescence properties. Thus, when going from n -hexane to methanol, the maximum emission wavelength λ em max shifts from 404 nm to 492 nm while φ r and τ increase from 1 to 17.7 and from 0.91 ns to 13.5 ns, respectively. These increments are still more accentuated in the presence of water with estimated values of 526 nm for λ em max , 27 for φ r and 20 ns for τ in this solvent. Because of the presence of a keto group which is a hydrogen bond acceptor and which can conjugate with the aromatic ring so as to provide the chromophore with a high dipole moment, the fluorescence properties of the probe strongly depend on the polarity of the surrounding medium. They can be accounted for in terms of general solvent effects (dipolar solute/solvent interactions) in the presence of aprotic solvents and in terms of specific solvent effects (hydrogen bonding) in protic solvents. Such properties of solvatochromism make the 2-anthroyl chromophore, after 8-(2-anthroyl)octanoic acid has been attached to phospholipids (E. Perochon and J.F. Tocanne (1991) Chem. Phys. Lipids 58, 7–17) a potential tool for studying microenvironmental polarity in biological membranes. |
| Databáze: | OpenAIRE |
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