On-Surface Annulation Reaction Cascade for the Selective Synthesis of Diindenopyrene,ACS Nano

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On-Surface Annulation Reaction Cascade for the Selective Synthesis of Diindenopyrene
ACS Nano ( IF 15.8 ) Pub Date : 2017-11-17 00:00:00 , DOI: 10.1021/acsnano.7b06459
Frank Eisenhut ₁ , Thomas Lehmann ₁ , Andreas Viertel ₂ , Dmitry Skidin ₁ , Justus Krüger ₁ , Seddigheh Nikipar ₁ , Dmitry A. Ryndyk _{1,

3} , Christian Joachim ₄ , Stefan Hecht ₂ , Francesca Moresco ₁ , Gianaurelio Cuniberti _{1,

5}

Affiliation

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.

中文翻译：

选择性合成二茚并py的表面环空反应级联

我们研究了4,10-双（2'-溴-4'-甲基苯基）-1,3-二甲基py的热诱导表面环化反应，以形成先前未知的非替代性聚芳烃二茚并[1,2,3-cd使用扫描隧道显微镜和光谱法在Au（111）上合成：1'，2'，3'-mn] py。观察到的单分子反应涉及热诱导的脱溴作用，然后进行选择性的闭环，以通过五元环融合相邻的苯部分。产品的结构已通过实验和理论验证。我们的结果表明，表面反应会引起异常的化学反应性和选择性，并提供了非交替的多芳族分子的通道。

更新日期：2017-11-19

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