Interfacial chemical oxidative synthesis of multifunctional polyfluoranthene

Abstract

A novel polyfluoranthene (PFA) exhibiting strong visual fluorescence emission, a highly amplified quenching effect, and widely controllable electrical conductivity is synthesized by the direct cationic oxidative polymerization of fluoranthene in a dynamic interface between n-hexane and nitromethane containing fluoranthene and FeCl₃, respectively. A full characterization of the molecular structure signifies that the PFAs have a degree of polymerization from 22–50 depending on the polymerization conditions. A polymerization mechanism at the interface of the hexane/nitromethane biphasic system is proposed. The conductivity of the PFA is tunable from 6.4 × 10⁻⁶ to 0.074 S cm⁻¹ by doping with HCl or iodine. The conductivity can be significantly enhanced to 150 S cm⁻¹ by heat treatment at 1100 °C in argon. A PFA-based chemosensor shows a highly selective sensitivity for Fe³⁺ detection which is unaffected by other common metal ions. The detection of Fe³⁺ likely involves the synergistic effect of well-distributed π-conjugated electrons throughout the PFA helical chains that function as both the fluorophore and the receptor units.