Nakamura Kimihiro, Li Qiang-Qiang, Krejčí Ondřej, Foster Adam S, Sun Kewei, Kawai Shigeki, Ito Shingo
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore.
Department of Applied Physics, Aalto University, Aalto 00076, Finland.
J Am Chem Soc. 2020 Jul 1;142(26):11363-11369. doi: 10.1021/jacs.0c02534. Epub 2020 May 15.
Heterocyclic [8]circulenes are an important class of polycyclic aromatic hydrocarbon molecules because of their unique structural properties and promising applications. However, the synthesis of heterocyclic [8]circulenes is still limited and thus is an important synthetic challenge. Here we describe the first example of a π-extended diaza[8]circulene surrounded by and fused with six hexagons and two pentagons, which was successfully synthesized only by a combined in-solution and on-surface synthetic strategy. State-of-the-art scanning tunneling microscopy with a CO-functionalized tip and density functional theory calculations revealed its planar conformation and unique electronic structure.
杂环[8]轮烯是一类重要的多环芳烃分子，因其独特的结构性质和广阔的应用前景而备受关注。然而，杂环[8]轮烯的合成方法仍然有限，因此是一项重要的合成挑战。本文报道了首例π-扩展二氮杂[8]轮烯，它由六个六边形和两个五边形环绕并融合而成，通过溶液合成与表面合成相结合的策略成功合成。利用具有CO功能化针尖的先进扫描隧道显微镜和密度泛函理论计算揭示了其平面构象和独特的电子结构。
