Institute for Materials Science, Max Bergmann Center of Biomaterials, and Center for Advancing Electronics Dresden, TU Dresden , 01069 Dresden, Germany.
Department of Chemistry & IRIS Adlershof, Humboldt-Universität zu Berlin , Brook-Taylor-Str. 2, 12489 Berlin, Germany.
ACS Nano. 2017 Dec 26;11(12):12419-12425. doi: 10.1021/acsnano.7b06459. Epub 2017 Nov 17.
We investigated the thermally induced on-surface cyclization of 4,10-bis(2'-bromo-4'-methylphenyl)-1,3-dimethylpyrene to form the previously unknown, nonalternant polyaromatic hydrocarbon diindeno[1,2,3-cd:1',2',3'-mn]pyrene on Au(111) using scanning tunneling microscopy and spectroscopy. The observed unimolecular reaction involves thermally induced debromination followed by selective ring closure to fuse the neighboring benzene moieties via a five-membered ring. The structure of the product has been verified experimentally as well as theoretically. Our results demonstrate that on-surface reactions give rise to unusual chemical reactivities and selectivities and provide access to nonalternant polyaromatic molecules.
我们使用扫描隧道显微镜和光谱学研究了 4,10-双(2'-溴-4'-甲基苯基)-1,3-二甲基芘在金(111)表面上的热诱导环化反应，形成了以前未知的非交替多环芳烃二茚并[1,2,3-cd:1',2',3'-mn]芘。观察到的单分子反应涉及热脱溴，然后通过五元环选择性环化，使相邻的苯环部分融合。该产物的结构已通过实验和理论得到验证。我们的结果表明，表面反应会产生不寻常的化学反应性和选择性，并为非交替多环芳烃分子的合成提供了途径。
