Synthesis of Fluorinated Fluoresceins
Citations Over TimeTop 10% of 1997 papers
Abstract
Several novel fluorinated fluoresceins (Oregon Green dyes) were prepared by the reaction of fluororesorcinols with phthalic anhydride and its derivatives. A novel regiospecific synthesis of fluororesorcinols was key to the successful synthesis of these new fluorophores. (Polyfluoro)nitrobenzenes were reacted with 2 equiv of sodium methoxide followed by reduction, hydrodediazoniation, and demethylation, giving the first straightforward synthesis of 2-fluororesorcinol, 4-fluororesorcinol, 2,4-difluororesorcinol, and 2,4,5-trifluororesorcinol. These fluorinated fluoresceins have higher photostability and ionize at a lower pH (pKa = 3.3−6.1) than fluorescein (pKa = 6.5). Some of the fluorinated fluoresceins have very high quantum yields (0.85−0.97), which, in combination with their lower pKas and high photostability, makes them superior fluorescent dyes for use as reporter molecules in biological systems.
Related Papers
- → A Review on Phthalic Anhydride Industry and Uses(2021)2 cited
- Ligand-Enhanced Nitrobenzene Attenuation Process in Subsurface Environment by Iron(II)(2011)
- Exploration of a New Method for Preparing Aniline from Nitrobenzene(2012)
- Study on Degradation of Nitrobenzene by Integrated Microbial-Fe~0 Treatment System(2009)
- Optimizing the parameters of biodegradating nitrobenzene by orthogonal design(2008)