Synthesis and Functionalization of New Chromophores for Organic Electronics & Photonics

High-performance organic electronic and photonic devices require optimization of both the core chromophore and the chromophores’ interactions in the solid state. Recently, we have been exploring the synthesis and implementation of larger chromophores - either linked trimeric systems or very long (> 8) fused-ring aromatic compounds to enhance both photonic properties and improve intermolecular contacts. Along with these new chromophores, we have developed new functionalization strategies to allow solution processing and to impart some control over the solid-state order of the cores. By this process, we have made a series of remarkably stable large aromatic systems with absorption well into the near-infrared. By tuning electronic coupling within chromophores, we have developed new singlet fission chromophores that yield quintet states exclusively. By tuning the functional groups on other systems, we have found approaches using C-H-π interactions to dramatically reduce disorder, and are studying the impact on charge transport. Due to their increased rigidity, we expect these larger polycyclic systems to demonstrate significant improvements in mobility. Thorough studies of decomposition mechanisms for these higher fused aromatic compounds have elucidated new reaction pathways, along with approaches to minimize reactions with oxygen or dimerization, yielding materials with unprecedented stability.