Dioxolane-Functionalized Hexacenes and Heptacenes Synthesis and Optical Properties Matthew J. Bruzek and John E. Anthony

The synthesis of dioxolane-functionalized hexacenes and heptacenes is reported. While heptacenes were too reactive to be successfully isolated, hexacenes showed higher stability and characteristic long-wavelength fluorescence both in solution and in the solid state as crystalline powders.

Acenes are among the most highly investigated aromatic semiconductor materials in organic electronics, leading to the development of functionalization strategies to increase their solubility, alter their crystal packing, and enhance their semiconducting properties. Although acenes as large as nonacene have been synthesized, pentacene and its derivatives dominate studies of semiconductor device performance due to the diminishing chemical stability of the larger acenes. Several years ago, we developed dioxolane-functionalized pentacenes and noted the enhanced fluorescence relative to pentacene. The addition of ethyl substituents orthogonal to the chromophore resulted in a highly stable material with strong, solid-state fluorescence useful for the fabrication of red light-emitting diodes and photovoltaics. Curious whether a similar strategy could be applied to larger acenes to enhance stability and solubility while yielding emission in the near-infrared, we describe here the synthesis and basic photophysical properties of dioxolane-functionalized hexacenes and heptacenes.

Synthesis and Optical Properties of Dioxolane-Functionalized Hexacenes and Heptacenes
Matthew J. Bruzek and John E. Anthony
Organic Letters Article ASAP

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