Semiconducting polymers have applications as active layer material in numerous technologies such as organic photovoltaics, sensors, and electronic displays. However, as performance metrics for these polymers increase, so does the synthetic complexity, which limits many of the highest performing polymers. Therefore, there is a need to develop simplified synthetic pathways to access conjugated monomers and polymers. Our work has utilized a robust synthetic pathway to synthesize dihalogenated conjugated monomers called dihydropyrrolopyrroles, or H2DPPs, in one synthetic step. The synthesis offers advantages compared to traditional preparation of conjugated monomers such as the reaction being run in air and does not require column chromatography for purification. H2DPPs subsequently can be polymerized using a variety of methods to yield conjugated polymers with tunable optical and electrochemical properties. In addition, dibrominated H2DPPs can be copolymerized with an assortment of comonomers, leading to differing optical and electronic properties dependent on the structure and functionalization of the comonomer. These properties, such as visible light absorbance, high fluorescence quantum yield, low oxidation potentials, and electrochromism, make H2DPPs suitable for myriad applications. Most notably, H2DPPs -based copolymers confer lower synthetic complexity than most of the conjugated polymers studied for organic photovoltaics or electrochromism. Due to the synthetic simplicity and tailorablity through monomer selection, our results offer a modular design motif for systematically engineering simple conjugated monomers and polymers for desired applications.

Conjugated polymers with low synthetic complexity based on electron-rich pyrrolopyrroles

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.