Copolymerization of Ferrocenylmethyl Acrylate and Ferrocenylmethyl Methacrylate with Organic Monomers

Abstract

Two novel ferrocene-containing monomers, ferrocenylmethyl acrylate, la (FMA), and ferrocenylmethyl methacrylate, lb (FMMA), have been synthesized. Both la and lb were copolymerized with styrene, methyl acrylate, methyl methacrylate, and vinyl acetate in benzene solutions initiated by azobisisobutyronitrile (AIBN) at 70°. Homogeneous copolymers were formed in each case, and the relative reactivity ratios of each copolymerization were determined. The values of n and r2 were:FMA (monomer l)-styrene = 0.02, r2 = 2.3; FMMA (monomer l)-styrene rr = 0.03, r2 = 3.7; FMA-methyl acrylate = 0.14, r2 = 4.46; FMMA-methyl acrylate = 0.08, r2 = 0.82; FMA-mefhyl methacrylate = 0.08, r2 = 2.9; FMMA-methyl methacrylate -0.12, r2 = 3.27; FMA-vinyl acetate r2 = 1.44, r2 = 0.46; and FMMAvinyl acetate r2 = 1.52, r2 = 0.20. While both FMA and FMMA are less reactive than other acrylates and methacrylates, they can be incorporated into copolymers which might have important commercial applications.

Progress on the synthesis and catalytic and anti‐migration properties of ferrocene‐based burning rate catalysts

“…Pittman et al reported homopolymerization of 2‐ferrocenylethyl acrylate and 2‐ferrocenylethyl methacrylate and the copolymerization 2‐ferrocenylethyl acrylate and methacrylate with styrene, methyl acrylate and methyl methacrylate. As shown in Scheme , both homo‐ and copolymerization were initiated by azobisisobutyronitrile (AIBN) in benzene or ethyl acetate solution at 60–80°C.…”

Sandwich Complex‐Containing Macromolecules: Property Tunability Through Versatile Synthesis

“…Other ferrocene‐containing monomers such as methacrylate and acrylate have been shown to undergo radical polymerization . For example, Pittman and co‐workers demonstrated the feasibility of AIBN‐catalyzed, free radical homopolymerization of ferrocenylmethyl acrylate and ferrocenylmethyl methacrylate in benzene solution.…”

“…For example, poly(ferroceneylmethyl acrylate) had T g in the range of 197–210 °C that was significantly higher than that of poly(methyl acrylate) . The Pittman group also reported the AIBN‐catalyzed, free radical homopolymerization of 2‐ferrocenylethyl acrylate and 2‐ferrocenylethyl methacrylate as well as the copolymerization of these monomers with styrene, vinyl acetate, methyl acrylate, and methyl methacrylate (Scheme ) . The homopolymerizations of these monomers, which were also first order in [monomer] and half order in [AIBN], afforded high‐molecular‐weights polymers ( = 14 700–82 300 g mol −1 ).…”

Size-dependent efficiency of electron transfer at suspended ferrocenyl jumbo particles

“…Petroleum ether (50 cm 3 ) was added drop-wise to the cooled mixture to precipitate the yellow copolymer, which was filtered, rinsed with a mixture of petroleum ether and benzene (2:1 volume) repeatedly and vacuumed to be dried. The ferrocenyl group was identified by UV-vis spectra of which specific band was at 435 nm [24].…”