Ferrocenyl monomers and polymers of N-allyl and N-acrylatenaphthalimides

A series of N-allyl, N-ethylmethacrylate and N-phenylmethacrylatenaphthalimide monomers have been prepared with -C=CFc, -C CFc and -C CSiMe3 substituents at the 4-position of the naphthalimide ring. All have been characterised by elemental analysis and spectroscopy; the X-ray structure of N-allyl-4-ethenylferrocenylnapththalimide is also reported. Free-radical polymerisation of these monomers gave homopolymers, random co- and terpolymers with polydispersities ranging from 1.7 to 3.2. Incorporation into a polymer matrix has no effect on the spectroscopic and electrochemical properties of the naphthalimide or ferrocenyl components. The ferrocenyl polymers are electrochromic and when oxidised give naphthalimide -> Fc(+) charge-transfer bands in the NIR; this electrochromism was examined by OTTLE techniques.