New perfluorocyclobutyl aryl ether-containing methacrylates: Synthesis and radical polymerization

Abstract

Three fluorine-containing methacrylate monomers consisting of one, two and three perfluorocyclobutyl (PFCB) aryl ether moieties were designed and synthesized through the esterification reaction between methacryloyl chloride and corresponding intermediates bearing different numbers of PFCB aryl ether moieties, which were achieved via an iterative elongation methodology. Subsequently, these methacrylate monomers were polymerized via conventional free radical polymerization in solution using AIBN as initiator to provide a series of polymethacrylate homopolymers with excellent solubility, whose repeat units contain one, two or three PFCB aryl ether moieties. The influence of the number of PFCB aryl ether moiety in each repeat unit on the light transmittance and surface wettability of the corresponding polymethacrylates were investigated by UV/vis spectroscopy and static water contact angle test. The results indicated that these polymethacrylates containing PFCB aryl ether moieties exhibit high transparency and strong hydrophobicity. It was also found from the results of thermogravimetry analysis that the initial decomposition temperatures of the resulting semi-fluorinated polymethacrylates comprising two and three PFCB aryl ether moieties are approaching 350 °C, which is much higher than that of common poly(methyl methacrylate), indicative of higher thermal stability of semi-fluorinated polymethacrylates in the presence of PFCB aryl ether moieties.