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Chapter 2

Fluoroalkylated Styrene Dimers: Synthesis, Properties, and Applications

Head-to-head type styrene dimers bearing two fluoroalkyl end-groups were efficiently synthesized by a simple reaction of a perfluoroalkyl iodide with styrene under radical conditions as a mixture of meso and racemic (rac) forms. The dimer is an interesting compound as the smallest model unit for fluoroalkyl end-capped oligomers and polymers for investigating the role of fluoroalkyl groups in functional materials. The isomers could be separated from each other by column chromatography and/or recrystallization. The meso form of the dimer 1 gave a crystal suitable for X-ray diffraction study and the crystal structure was found to be based on π,π-stacking of benzene rings and aggregation of fluoroalkyl chains. Among the various substituted styrene dimers on the benzene rings, 4-hydroxylated styrene dimers (2) were found to exhibit unique properties on the basis of their self-assembly. The OH groups on the benzene rings may work effectively for the self-assembly of the dimers in addition to the π,π-stacking of the benzene rings and aggregation of the fluoroalkyl chains. Especially rac-2 worked as the host molecule for inclusion of alcohols on recrystallization from hexane with a small amount of alcohol. The synthesized styrene dimers are expected to have high potential as novel fluorinated functional materials.

Publication details

Print publication date
28 Oct 2016
Copyright year
Print ISBN
ePub eISBN
From the book series:
Polymer Chemistry Series