Rhodamine F: a novel class of fluorous ponytailed dyes for bioconjugation

Abstract

Incorporation of fluorous ponytails such as polyfluorinated alkyl residues (CH2)m(CF2)nCF3 leads to a novel class of bright rhodamine-based fluorescence dyes. These dyes combine the excellent photophysical properties of the frequently used rhodamine dyes with the unique features of "light" fluorous molecules. One of those features is the possibility to separate substances utilizing fluorous solid-phase extraction (F-SPE), which is based on the specific intermolecular interaction between fluorous compounds. Thus, molecules, which are labeled with these new dyes, are not only accessible to fluorescence experiments, but can also be easily purified (via so-called FluoroFlash columns) prior to use. The dyes were bound to a cell penetrating peptoid (polycationic oligo(N-substituted) glycine) on solid supports. These conjugates were purified with F-SPE before their photophysical and biological properties were investigated.

Surface modification of polymers with bis(arylcarbene)s from bis(aryldiazomethane)s: preparation, dyeing and characterization

“…This step is required because the strongly electron-withdrawing nitro group makes the amino group very inert, which does not react with perfluoroalkyl iodide. Two kinds of perfluoroalkyl iodide with different numbers of CF 2 unit were then reacted with 18 to generate 19(f~g) 34,35 , and subsequent cleavage of trifluoroacetyl group gave 20(f~g). Finally, fluoroamines 20(f~g) were treated with isoamyl nitrite to give fluoro-diazonium salts 15(f~g).…”

New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria

“…Examples of polyfluorinated rhodamine dyes 2 and 3. [28] Scheme1.Synthesis of the polyfluorinated heterocycles 8a, b,a nd c.…”

Application of Fe3O4@Silica Sulfuric Acid as a Magnetic Nanocatalyst for the Synthesis of Rhodamine Derivatives

“…The synthesis of rhodamines using a wide range of inorganic or organic acids such as ZnCl 2 , H 3 PO 4 , H 2 SO 4 , and PTSA are reported. ZnCl 2 is corrosive to metals.…”

“…Sulfuric acid is very corrosive . PTSA have limitations, such as non‐recyclable, prolonged reaction time (24 h), high temperature (160 °C), low yield (24%), and use of hazardous solvents like propionic acid . This justifies significant scope for the development of a noble catalyst for the synthesis of rhodamines via the facile, efficient and environmentally‐friendly protocol.…”