Wang Qiang, Wang Wei-Zhen, Zhang Ruiying, Zhai Zi'ang, Chen Xinyu, Li Minggang, Jin Yi, Zhu Lingyun, Li Yuanming, Ye Ke-Yin
Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China.
Key Laboratory of Advanced Carbon-Based Functional Materials (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China.
JACS Au. 2025 Sep 1;5(9):4281-4287. doi: 10.1021/jacsau.5c00653. eCollection 2025 Sep 22.
This study presents an efficient method for synthesizing twisted benzo-extended []-phenacenes ([]-BPs) featuring an electrochemical flow (e-flow) Scholl reaction of the corresponding []-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 []-BPs and thus tunes their photophysical properties. This work provides a green and sustainable synthetic strategy for diverse []-BPs and enables facile bandgap modulation through π-conjugation extension, offering potential for organic semiconductor applications in optoelectronic devices.
本研究提出了一种高效的方法来合成扭曲的苯并扩展的[]-菲（[]-BPs），该方法通过一锅三组分铃木-宫浦偶联反应，对相应的[]-BP前体进行电化学流动（e-flow）肖尔反应。e-flow肖尔反应具有减少氧化剂用量和过氧化副产物、通过延长电解时间易于放大生产等优点，适用于这些复杂的多环芳烃。此外，分子长度的增加降低了[]-BPs的光学带隙，从而调节了它们的光物理性质。这项工作为多种[]-BPs提供了一种绿色可持续的合成策略，并通过π共轭扩展实现了轻松的带隙调制，为光电器件中的有机半导体应用提供了潜力。
