期刊
ACS NANO
卷 11, 期 12, 页码 12419-12425出版社
AMER CHEMICAL SOC
DOI: 10.1021/acsnano.7b06459
关键词
on-surface reaction; single-molecule chemistry; scanning tunneling microscopy; nonalternant polyaromatic hydrocarbons; density functional theory; reaction mechanism
类别
资金
- ICT-FET European Union Integrated Project ATMOL
- PAMS
- German Excellence Initiative via the Cluster of Excellence Center for Advancing Electronics Dresden (cfaed) [EXC1056]
- International Helmholtz Research School Nanonet
- German Research Foundation [SFB 951]
We investigated the thermally induced on surface cyclization of 4,10-bis(2'-bromo-4'-methylpheny1)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.
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