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“奥运烯”苯并[cd]芘的合成与扫描隧道显微镜/原子力显微镜成像

The synthesis and STM/AFM imaging of 'olympicene' benzo[cd]pyrenes.

作者信息

Mistry Anish, Moreton Ben, Schuler Bruno, Mohn Fabian, Meyer Gerhard, Gross Leo, Williams Antony, Scott Peter, Costantini Giovanni, Fox David J

机构信息

Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, CV4 7AL (UK).

出版信息

Chemistry. 2015 Jan 26;21(5):2011-8. doi: 10.1002/chem.201404877. Epub 2014 Dec 2.

DOI:10.1002/chem.201404877
PMID:25469908
Abstract

H-Benzo[cd]pyrene ('Olympicene') is a polyaromatic hydrocarbon and non-Kekulé fragment of graphene. A new synthetic method has been developed for the formation of 6H-benzo[cd]pyrene and related ketones including the first time isolation of the unstable alcohol 6H-benzo[cd]pyren-6-ol. Molecular imaging of the reaction products with scanning tunnelling microscopy (STM) and non-contact atomic force microscopy (NC-AFM) characterised the 6H-benzo[cd]pyrene as well as the previously intangible and significantly less stable 5H-benzo[cd]pyrene, the fully conjugated benzo[cd]pyrenyl radical and the ketones as oxidation products.

摘要

H-苯并[cd]芘(“奥运烯”)是一种多环芳烃,也是石墨烯的非凯库勒片段。已开发出一种新的合成方法来制备6H-苯并[cd]芘及相关酮类,其中首次分离出了不稳定的醇6H-苯并[cd]芘-6-醇。利用扫描隧道显微镜(STM)和非接触原子力显微镜(NC-AFM)对反应产物进行分子成像,表征了6H-苯并[cd]芘以及之前难以捉摸且稳定性明显较低的5H-苯并[cd]芘、完全共轭的苯并[cd]芘基自由基和作为氧化产物的酮类。

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