Electron-Deficient Contorted Polycyclic Aromatic Hydrocarbon via One-Pot Annulative π‑Extension of Perylene Diimide

The
synthesis of a class of contorted electron-deficient polycyclic
aromatic hydrocarbons (PAHs) has been achieved by a one-pot bay annulation
of perylene diimide involving a mild Suzuki coupling and subsequent
air-mediated, ambient-light-induced photocyclization. X-ray crystallography
unambiguously confirmed the contorted PAH structure bearing four imide
groups. The photophysical and electronic properties of these contorted
PAHs were also analyzed, showing a high fluorescence quantum yield
of 86% and moderate electron mobility of 0.017 cm2 V–1 s–1.

本研究通过基于苝二酰亚胺（perylene diimide）的一锅法海湾区环化反应，成功实现了一类扭曲型缺电子多环芳烃（polycyclic aromatic hydrocarbons, PAHs）的合成，该反应包含温和的铃木偶联（Suzuki coupling）步骤，以及后续空气介导、环境光诱导的光环化反应（photocyclization）。X射线晶体衍射（X-ray crystallography）明确证实了这类带有四个酰亚胺基团的扭曲多环芳烃的分子结构。本研究还对该类扭曲多环芳烃的光物理与电子性质开展了分析，结果显示其荧光量子产率（fluorescence quantum yield）高达86%，电子迁移率为0.017 cm² V⁻¹ s⁻¹，属于中等水平。