A neo-pentyl-ferrocene motif for the synthesis of electroactive polyesters

Several new neo-pentylenediol based ferrocenyl molecules have been prepared using Friedel–Crafts acylation and Clemmensen reduction techniques. The acyl or methyl linker by which the ferrocenyl group is attached tunes the redox properties of the small molecule. The X-ray crystal structure of the acylferrocene with protecting ester groups, its derivative dialcohol, and the methylferrocene dialcohol compounds are reported. Melt polymerisation conditions result in an elimination from the acyl monomer, but a mild carbodiimide coupling protocol successfully generates a number of neo-pentylenediol/aromatic dicarboxylate polyesters with pendant ferrocenyl groups.

Graphical abstractThe article contains synthesis and characterisation details of new ferrocenyl substituted diols suitable for polyesterification. Three crystal structure determinations are reported including a diester model of the polymer repeating unit. Electrochemistry of the ferrocene molecules is discussed, and an example given of a successful polymerisation with terephthalic acid.Figure optionsDownload full-size imageDownload as PowerPoint slide