Development of Mechanically Robust Pyrrolopyrrole Chromophores

Introduction of functionalities to pyrrolopyrrole (H2DPP) chromophores is essential for tailoring properties but many reactions to accomplish this result in accessing materials with low reaction yields. In an effort to improve these reactions and access materials with diverse properties we developed polymerizations of 1,4-dihydroxyDPP and sebacoyl chloride. Successful reactions are evident by a distinct change in the solubility and perceived color compared to the respective starting materials. The structural diversity was then expanded by synthesizing polyesters with varying substitution patterns on the pyrrolopyrroles. This structural variation results in drastic color change dependent on chemical functionality on the H2DPP, suggesting potential color control strategies for lightweight, flexible electronics. Results from this work provide a new synthetic approach for functionalizing electron rich pyrrolopyrroles and enable, and motivate, continued investigations into structure-property relationships of novel chromophores and polymers