Revisiting Kekulene: Synthesis and Single-Molecule Imaging
Revisiting Kekulene: Synthesis and Single-Molecule Imaging
复制标题
DOI：
10.1021/jacs.9b07926
复制
发表时间：
2019-10-02
影响因子：
15
通讯作者：
Perez, Dolores
中科院分区：
文献类型：
--
作者：
Pozo, Iago;Majzik, Zsolt;Perez, Dolores
在第一次（也是唯一一次）报道合成kekulene的四十年后，这种象征性的环芳烃再次通过改进的路线获得，该路线涉及通过苯乙烯和多功能苯并二炔合成子之间的双Diels-Alder反应构建关键合成中间体5，6，8，9-四氢苯并[m]四苯。超高分辨率的原子力显微镜成像的单分子的kekulene和计算计算提供了额外的支持的分子结构与显着程度的键本地化根据共振结构预测的克拉尔模型。
Four decades after the first (and only) reported synthesis of kekulene, this emblematic cycloarene has been obtained again through an improved route involving the construction of a key synthetic intermediate, 5,6,8,9-tetrahydrobenzo[m]tetraphene, by means of a double Diels-Alder reaction between styrene and a versatile benzodiyne synthon. Ultra-high-resolution AFM imaging of single molecules of kekulene and computational calculations provide additional support for a molecular structure with a significant degree of bond localization in accordance with the resonance structure predicted by the Clar model.