Unlike closed-shell compounds, open-shell compounds have unpaired electrons that reside in non-bonding molecular orbitals. Stabilization of unpaired electron density through π-delocalization enables open-shell compounds to demonstrate unique optoelectronic properties that are not accessible to their closed-shell counterparts. Additionally, these properties can be electronically tuned by incorporating heteroatoms into the π-conjugated backbone. Here I will present the synthesis of an open-shell N-substituted bisphenalenyl π-radical cation and our investigations into its optoelectronic properties. Its molecular structure was confirmed by X-ray diffraction, and conductive single crystals (1.3 x 10-2 S/cm) revealed that unusually close π-stacking interactions occur in the solid-state. The ambient stable π-radical cation showed fluorescence through doublet emission and notably demonstrated one of the highest photostabilities amongst luminescent organic radicals. Furthermore, conductive films of the π-radical cation can achieve balanced hole and electron mobilities (μe/μh ≥ 1.48 × 10-2 cm2 V-1 s-1) in FET devices, which is an extremely rare example of a small molecule material capable of ambipolar conduction.

N-substituted open-shell π-conjugated material: Synthesis and optoelectronic properties

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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