Functionalized polycyclic aromatic hydrocarbons (PAHs) are essential building blocks for the bottom-up fabrication of structurally uniform nanocarbons. Herein we report a simple and efficient synthetic method toward K-region hydroxy-functionalized PAHs via TEMPO-mediated twofold intramolecular C–H/C–H arylations of 1-biphenyl-2-yl-2-aryl-ethanone derivatives. This method achieves high yields and selectivity, synthesizing a variety of PAH frameworks, including pyrenes, chrysenes, benzo[c]phenanthrenes, and benzo[k]tetraphenes. Our results also demonstrate the potential of these compounds as valuable candidates for the selective construction of larger PAH structures.

中文翻译：

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通过两倍分子内 C-H/C-H 芳烃直接合成 K 区官能化多环芳烃


功能化多环芳烃 （PAH） 是自下而上制造结构均匀的纳米碳氢化合物的重要组成部分。在此，我们报道了一种简单有效的合成方法，通过 TEMPO 介导的 1-联苯-2-基-2-芳基-乙酮衍生物的两倍分子内 C-H/C-H 芳基化 K-区羟基官能化 PAHs。该方法实现了高产率和选择性，合成了多种 PAH 框架，包括芘、菊、苯并[c]菲和苯并[k]四酚。我们的结果还证明了这些化合物作为选择性构建更大 PAH 结构的宝贵候选者的潜力。