Pyromellitic diimide (PMDI), also known as pyromellitimide, is the smallest in the series of aromatic diimides that are attractive for organic optical and electronic applications because of their tendency to undergo reversible redox behavior and display intense optical properties. The small aromatic core of PMDI results in more difficult to access reduced redox states due to lesser stabilization by conjugation and increased proximity of imide redox sites. To tackle this challenge, with the ultimate aim of achieving ambient-stable PMDI reduced states, we targeted the derivatization of PMDI with cationic groups. Here, we present 1) development of microwave-assisted synthetic approaches for PMDI functionalization, 2) photophysical characterization of PMDIs singly and doubly functionalized with pyridinium and phosphonium groups, and 3) unexpected core substitution chemistry of PMDI that takes place at elevated temperatures.

Enhancing pyromellitic diimide electron acceptor ability through cationic core functionalization

2019 Spring National Meeting

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