Biodegradable Polyimidazole Particles as Contrast Agents Produced by Direct Arylation Polymerization

Conjugated polymer particles provide an important platform for the development of theranostic nanoagents. However, the number of biocompatible and foremost biodegradable π-conjugated polymers is limited. Imidazole is a π-conjugated motif that is abundant in biological systems. Oxidative degradation of imidazole is present in nature via enzymatic or free radical processes. In this work, we introduce polymer particles consisting purely of polyimidazole. We employ direct arylation polymerization and adapt it to a dispersion polymerization protocol to yield uniform and narrowly dispersed nanoparticles. We employ this mechanism to produce linear and cross-linked polymer particles to tune the optical properties from fluorescent to photoacoustically active. We show that the particles can be degraded by H₂O₂ as well as by reactive oxygen species produced by cells and we detect the degradation products. Altogether, our results suggest that polyimidazole particles represent ideal candidates for theranostic applications.