Thiol-Michael-Functionalized Polypyrrole Nanoparticles with Intrinsic Fluorescence and Electroactivity

Polypyrrole is functionalized by deprotonation of its oxidized state, followed by a thiol-Michael addition reaction. It is found that this process produced emissive compositions. This feature is found to be diagnostic of the functionalization and relative solvation by water, wherein enhanced interactions with the solvent gave higher emission intensities. The thiol-conjugation method is shown to be general and can be extended to a range of polar, nonpolar, and aromatic materials. Thiol-conjugated materials retain the electroactivity characteristic of polypyrrole. The dual fluorescence and electroactivity of these thiol-conjugated nanoparticles suggest their potential as a sensing platform.