A novel fluorinated monomer: Synthesis, characterization and ATRP of 5,6,7,8-tetrafluoronaphthalen-1-yl acrylate

Abstract

A new fluorinated naphthyl-acrylate based monomer was synthesized in three steps, namely the addition reaction of furan via Diels Alder cycloaddition reaction, acid catalyzed aromatization reaction and Schotten-Baumann esterification reaction, respectively. The structure of the precursors and the target compound was characterized comprehensively by FT-IR, UV-vis, H-1 NMR, C-13 NMR, F-19 NMR and LC-MS/MS measurements. Atom transfer radical polymerization (ATRP) was used for the polymerization of 5,6,7,8-tetrafluomnaphthalen-1-yl acrylate. The successful polymerization of this novel monomer was verified by FT-IR and GPC analyses. Particularly, DSC and TGA analyses showed that the poly(5,6,7,8-tetrafluoronaphthalen-1-yl acrylate) has a glass transition temperature of 105-110 degrees C and starts to degrade after 150 degrees C. The results showed that the proposed monomer can be synthesized in yields overpassing 80 % by using the aforementioned reaction sequence. Our results revealed that 5,6,7,8-tetrafluom naphthalen-1-yl acrylate could be acceptable as a promising monomer candidate in the field of synthetic polymer chemistry.