Benzo-Extended [n]Phenacenes: e‑Flow Synthesis and Length-Dependent Properties

苯并扩展的[n]菲并苯:电子流合成及长度依赖性性质

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Abstract

This study presents an efficient method for synthesizing twisted benzo-extended [n]-phenacenes ([n]-BPs) featuring an electrochemical flow (e-flow) Scholl reaction of the corresponding [n]-BP precursors from a one-pot three-component Suzuki-Miyaura coupling reaction. The e-flow Scholl reaction offers advantages such as reduced oxidant usage and overoxidation byproducts, and easy scale-up through extended electrolysis time toward these intricate polycyclic aromatic hydrocarbons. In addition, the increase in molecular length decreases the optical bandgap of [n]-BPs and thus tunes their photophysical properties. This work provides a green and sustainable synthetic strategy for diverse [n]-BPs and enables facile bandgap modulation through π-conjugation extension, offering potential for organic semiconductor applications in optoelectronic devices.

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