Synthesis and Photophysical Properties of a Series of Cyclopenta[b]naphthalene Solvatochromic Fluorophores
| Autor: | Laura S. Kocsis, Erica Benedetti, Kay M. Brummond |
|---|---|
| Rok vydání: | 2012 |
| Předmět: |
Fluorophore
Cycloaddition Reaction Solvatochromism Electrons General Chemistry Naphthalenes Photochemistry Biochemistry Catalysis Coupling reaction Solvent chemistry.chemical_compound symbols.namesake Spectrometry Fluorescence Colloid and Surface Chemistry chemistry Stokes shift symbols Amines Methylene Absorption (chemistry) Palladium Styrene Derivative (chemistry) Fluorescent Dyes |
| Zdroj: | Journal of the American Chemical Society. 134:12418-12421 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja3055029 |
| Popis: | The synthesis and photophysical properties of a series of naphthalene-containing solvatochromic fluorophores are described within. These novel fluorophores are prepared using a microwave-assisted dehydrogenative Diels-Alder reaction of styrene, followed by a palladium-catalyzed cross coupling reaction to install an electron donating amine group. The new fluorophores are structurally related to Prodan. Photophysical properties of the new fluorophores were studied and intriguing solvatochromic behavior was observed. For most of these fluorophores, high quantum yields (60-99%) were observed in methylene chloride in addition to large Stokes shifts (95-226 nm) in this same solvent. As the solvent polarity increased, so did the observed Stokes shift with one derivative displaying a Stokes shift of ~300 nm in ethanol. All fluorophore emission maxima, and nearly all absorption maxima were significantly red-shifted when compared to Prodan. Shifting the absorption and emission maxima of a fluorophore into the visible region increases its utility in biological applications. Moreover, the cyclopentane portion of the fluorophore structure provides an attachment point for biomolecules that will minimize disruptions of the photophysical properties. |
| Databáze: | OpenAIRE |
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