Organofluorine compounds have been widely used in industrial and consumer applications, owing to their specific characters such as high thermal and chemical stability. After it became clear that some of them, particularly, perfluorooctanesulfonate (PFOS) and perfluorooctanoic acid (PFOA), bioaccumulate in the environment, international legal measures regarding the production, use, and import and export of several organofluorine compounds are being implemented. Hence, it is desirable to develop effective methodologies for decomposing these compounds to environmentally harmless species under mild conditions. If they could be decomposed to F^– ions by means of environmentally benign techniques, the well-established protocol for the treatment of F^– ions could be used: Ca²⁺ is added to the system to form CaF₂, which is a raw material for hydrofluoric acid. Thus, the development of such techniques would allow for the recycling of fluorine resource, the global demand for which is increasing. We describe herein the international regulatory trend for organofluorine compounds. We also describe our developed methodologies for efficient decomposition of cutting-edge fluorinated materials (ionic liquid and polymers) to F^– ions.

Fluoroalkylacrylate (FA) polymers are widely used as fluorine-based water and oil repellents for various materials such as textiles, carpets, papers, etc. Water repellency can also be given with silicone-based polymers and hydrocarbon polymers but, with FA polymers, even higher resistance to water pressure, better oil repellency, and antifouling properties can be attained and, for that reason, generally fluorine-based systems are currently employed as water and oil repellents.

In recent years, extensive investigations and researches have been carried out because of increasing concerns due to the accumulation in the environment and the living body of perfluorooctanoic acid (PFOA) derived from fluorotelomers which constitute the raw material of FA polymers.

In this review we give an overview of the PFOA issue, the production process of FA polymers, touching on the relationship between the water-repellent performance of FA polymers and their structures. Furthermore, we discuss the future prospects of alternative technologies to produce environmentally friendly (short chain type) fluorine-based water and oil repellents as well as PFOA-free type of these products.

An organic compound involving a perfluoroalkyl (Rf) group exhibits unique bulk properties, which cannot be replaced by a normal hydrocarbon compound. Representative properties such as the surface hydrophobicity, a low electric permittivity and a high melting point have long been an unresolved chemical matter especially when they are related to the primary structure. In this article, a new theoretical framework of the stratified dipole-arrays (SDA) theory on electrodynamics is described for comprehensive understanding of the properties of an Rf compound in terms of a single Rf and aggregated Rf groups in a separated manner.

As possible materials for structural and functional characterization of membrane proteins in vitro, we have developed novel partially fluorinated phospholipids that are modified with the substitution of the terminal alkyl group in the myristoyl chains of dimyristoylphosphatidylcholine (DMPC) by the perfluoroalkyl (C_nF_2n+1 ) group at different lengths. Differential scanning calorimetric (DSC) measurements were performed for the novel partially fluorinated phospholipids Fn-DMPC (n=2,4,6,8). DSC curves of Fn-DMPC suspension demonstrated that Fn-DMPC suspension has significant Rf chain length-dependent gel-to-liquid crystalline phase transition temperature (Tm): Fn-DMPC with the short Rf groups (n=2,4,6) has lower Tm than unfluorinated DMPC, while Tm dramatically elevated to ~66°C upon elongation of the Rf group to n=8. We have also investigated structural and functional properties of a photoreceptor membrane protein bacteriorhodopsin (bR) incorporated into F4-DMPC liposome. As the result, bR in F4-DMPC liposome adopts native-like higher order structure and photocycle both in the gel and the liquid crystalline phase, which is in stark contrast with phase transition-induced structural changes for bR in DMPC liposome. These experimental results suggest that partially fluorinated phospholipid is promising for biochemical and biophysical studies of membrane proteins.

Fluorine-containing organic compounds have been receiving significant interest in material science and pharmaceutical chemistry. Especially, fluorinated amino acids are promising compounds to contribute to the further development of biochemistry and medicinal chemistry. However the reports on stereoselective synthesis of perfluoroalkylated α-amino acids are limited. This review summarizes the synthetic methods of perfluoroalkylated amino acids based on the naturally occurring amino acids, alanine, valine, leucine, isoleucine.