Abstract
Head-to-head-type styrene and substituted styrene dimers bearing two fluoroalkyl end-groups have been efficiently synthesized by a simple reaction of perfluoroalkyl iodide with styrene under radical conditions as a mixture of meso and racemic forms. The meso form obtained from the mixture by recrystallization gave a crystal suitable for X-ray diffraction study and the crystal structure was found to be based on π-stacking of benzene rings and aggregation of fluoroalkyl chains. Dynamic light scattering measurements showed that meso-styrene dimers bearing two fluoroalkyl end-groups can form the nanometer size-controlled self-assemblies through the intermolecular π-stacking of benzene rings and aggregation of end-capped fluoroalkyl groups in methanol.
Self-assembled meso-perfluorohexylated styrene dimer [C6F13–CH2CHPh–CHPh–CH2–C6F13] based on π-stacking of benzene rings and aggregation of fluoroalkyl chains: Fluorous domains are constructed by self-assembly of fluoroalkyl chains.
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This work was partially supported by a Grant for Hirosaki University Institutional Research, for which the authors from Hirosaki are grateful.
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Iizuka, M., Fukushima, S., Goto, Y. et al. Synthesis and application of head-to-head-type styrene dimers bearing two fluoroalkyl end-groups. Colloid Polym Sci 291, 595–601 (2013). https://doi.org/10.1007/s00396-012-2761-4
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DOI: https://doi.org/10.1007/s00396-012-2761-4