Organofluorine chemistry

Organofluorine chemistry is the branch of organic chemistry that deals with organic compounds containing fluorine. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, refrigerants, and reagents in catalysis. In addition to these applications, some organofluorine compounds are pollutants because of their contributions to ozone depletion, global warming, bioaccumulation, and toxicity. The area of organofluorine chemistry often requires specialized knowledge and techniques.

History

The history of organofluorine chemistry begins with the discovery of fluorine in 1886 by Ferdinand Frederic Henri Moissan. Early pioneers in organofluorine chemistry include such individuals as Fritz Rozen, who first prepared the simple fluorocarbons in 1892.

Properties

Organofluorine compounds often persist in the environment due to the strength of the carbon–fluorine bond. Fluorine has the highest electronegativity of all elements: 3.98 on the Pauling scale. Polymers with fluorinated substituents exhibit reduced surface energies and thus improved properties relative to the corresponding hydrocarbon-based polymers.

Applications

Organofluorine compounds are used in many applications, including pharmaceuticals, agrochemicals, and surfactants. They are also used in the production of refrigerants and aerosols.

Environmental Impact

Some organofluorine compounds are pollutants because of their contributions to ozone depletion, global warming, bioaccumulation, and toxicity. The Montreal Protocol targeted the phase-out of chlorofluorocarbon (CFC) and hydrochlorofluorocarbon (HCFC) refrigerants due to concerns about their stability and the potential for release of fluorine atoms by UV irradiation.

See Also

• Fluorine
• Organic chemistry
• Ferdinand Frederic Henri Moissan
• Fritz Rozen
• Montreal Protocol

References

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  Montage of various fluorocarbon structures

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  Example of an aliphatic fluorocarbon

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  Example of an aromatic fluorocarbon

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  Reaction involving Selectfluor

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  Preparation of fluorodeoxyglucose (FDG)

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  Structure of the enzyme fluorinase