fluorous

Fluorous refers to a class of compounds characterized by the presence of multiple fluorine atoms, typically attached to a carbon chain. These compounds, often referred to as perfluorinated compounds or fluorocarbons, exhibit unique chemical and physical properties due to the strong carbon-fluorine bond. This bond is highly polarized and very stable, leading to a low surface tension, high thermal stability, and resistance to chemical degradation.

The term "fluorous" is commonly used in the context of fluorous chemistry, a field that utilizes these unique properties for various applications, particularly in separation science and organic synthesis. Fluorous tags, which are short perfluorinated chains, can be attached to molecules of interest. These tags are soluble in fluorous solvents but insoluble in common organic and aqueous solvents. This differential solubility allows for efficient separation and purification of tagged molecules using fluorous solid-phase extraction or fluorous liquid-liquid extraction techniques.

In organic synthesis, fluorous tags can serve as protecting groups or as handles for directing reactions. After the desired chemical transformations are complete, the fluorous tag can be easily cleaved off, leaving the purified product. This approach has been developed as a "fluorous phase synthesis" or "fluorous solid-phase synthesis" methodology, offering advantages in terms of purification efficiency and potential for automation.

Beyond synthesis, fluorous compounds themselves find applications as lubricants, surfactants, refrigerants, and in specialized coatings due to their inertness and low friction characteristics. The high electronegativity of fluorine atoms significantly influences the electron distribution within the molecule, contributing to its distinctive behavior.