Synthesis of highly fluorescent water-soluble polypyrrole for cell imaging and iodide ion sensing

Abstract

Conjugated polymers for bioimaging and sensing chemical/biological reagents have received much attention owing to their outstanding photophysical properties. However, most conventional synthetic strategies result in aggregates of conjugated polymers with limited solubility in most common organic and aqueous solvents. Therefore, advancement in molecular design and synthetic pathways is required to tune the optical and solubility properties of the resulting conjugated polymers. Herein, a simple, general, and effective approach for the synthesis of water-soluble polypyrrole (PPy) is reported based on the chemical polymerization in the presence of a homologue series of dicarboxylic acids with different chain lengths as multifunctional dopant molecules, possessing two carboxylic acid groups which serve as both dopants and stabilizing agents. The role of dopant chain length on the emission properties of resulting water-soluble polymers has been investigated. Among the synthesized water-soluble polymers, succinic acid-stabilized polymer (PPy-Suc) showed the highest emission wavelength (λem = 453 nm), high quantum yield (12.87), very good photostability and low cytotoxicity, suggesting its applicability in bioimaging and sensing applications. As a proof of concept, the PPy-Suc polymer was successfully utilized in cellular imaging. Moreover, a novel fluorescence iodide sensor with two linear ranges of 0.012–0.200 and 0.200–8.825 μM and a low detection limit of 9 nM was developed based on the prepared PPy-Suc polymer. The superior properties of the synthesized water-soluble polymers confirm the potential applicability of developed method as a general, facile and effective synthesis approach in preparation of water-soluble conjugated polymers with several potential applications.