#fluorous

[whats-in-a-sentence]

We are investigating this approach in the design of functional fluorous surfactants based on small heterocyclic compounds (figure 18.18).

"Chemistry" 2e - Blackman, A., Bottle, S., Schmid, S., Mocerino, M., Wille, U.

[labphoto]

Distillation of a quite interesting compound, an aryl-perfluoroalkyl disulfide. 

Trifluoromethyl disulfides are important as precursors of biologically active trifluoromethyl thiosulfonates and important parts of molecules being developed for modern medicinal chemistry. Good point: I recently found a cheap and well scalable method for the preparation of this functional group.

[labphoto]

Another snapshot from fluorous chemistry. Under the organic layer that small yellow oily layer is a highly fluorous.

Fluorous chemistry involves the use of perfluorinated compounds or perfluorinated substituents to facilitate recovery of a catalyst or reaction product. Perfluorinated groups impart unique physical properties including high solubility in perfluorinated solvents. 

A perfluorinated compound (PFC) is an organofluorine compound containing only carbon-fluorine bonds (no C-H bonds) and C-C bonds but also other heteroatoms. PFCs have properties that represent a blend of fluorocarbons (containing only C-F and C-C bonds) and the parent functionalized organic species. For example, perfluorooctanoic acid functions as a carboxylic acid but with strongly altered surfactant and hydrophobic characteristics.

For more:  István T. Horváth (Ed.) Topics in Current Chemistry 2011: "Fluorous Chemistry"  http://link.springer.com/chapter/10.1007%2F128_2011_282

[labphoto]

Experimenting with fluorous chemistry. 

Route to a publication: 

1: you observed something what you think is new and worth to write it down

2: read a lot after this till you are sure that you discovered something new

3: reproduce it and try it with n+1 other compounds 

4: try it out on larger scale

5: write it down and publish it somewhere

Currently the third step is seen on the picture. You may ask that why is No.1 vial missing... It overreacted right after measuring in the reactants.

[labphoto]

Something interesting: a classical demonstration in fluorous chemistry: 3 non miscible layers (organic-aqueous -fluorous).

The upper layer is an organic solution: Sudan IV (a red colored azo dye) dissolved in toluene.

The middle layer is water and methanol.

The bottom layer is a fluorous solution: perfluoroalkylated cobalt phthalocyanine (a blue colored complex) dissolved in perfluoroperhydrophenanthrene.