Ferrocene clicked polypyrrole derivatives: Effect of spacer group on electrochemical properties and post-polymerization functionalization
Özet
In this study, novel ferrocene-functionalized N-alkyl substituted pyrrole derivatives, namely
4-ferrocenyl-1-[3-(pyrrol-1-yl)propyl]-1H-1,2,3-triazole (Py3Fc), 4-ferrocenyl-1-[4-(pyrrol-1-yl)butyl]-
1H-1,2,3-triazole (Py4Fc), and 4-ferrocenyl-1-[6-(pyrrol-1-yl)hexyl]-1H-1,2,3-triazole (Py6Fc), were
synthesized via click reaction and the monomers were characterized by 1H NMR, 13C NMR, FTIR, and
HRMS techniques. Redox properties of the monomers were investigated by cyclic voltammetry (CV)
studies. Contrary to general literature, both Py4Fc and Py6Fc were electrochemically polymerized
without loss in redox activity of ferrocene group. Moreover, click chemistry was utilized in postpolymerization functionalization. For this purpose, three azide-containing polypyrroles, P(Py3N3),
P(Py4N3), and P(Py6N3) were electrochemically synthesized and subjected to click reaction in the
presence of ethynylferrocene. CV studies of the post-polymerization functionalized polymers
revealed quasi-reversible waves, while only P(Py6-post-Fc) showed the characteristic redox behavior
of both polypyrrole and ferrocene. Thus, in this study preparation of a conducting homopolymers
of pyrrole having covalently bonded ferrocene units was demonstrated and effect of spacer group
is investigated.
