On-Surface Strain-Driven Synthesis of Nonalternant Non-Benzenoid Aromatic Compounds Containing Four- to Eight-Membered Rings,Journal of the American Chemical Society

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On-Surface Strain-Driven Synthesis of Nonalternant Non-Benzenoid Aromatic Compounds Containing Four- to Eight-Membered Rings
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2021-08-11 , DOI: 10.1021/jacs.1c06168
Benjamin Mallada _{1,

2} , Bruno de la Torre _{1,

2} , Jesús I Mendieta-Moreno ₂ , Dana Nachtigallová _{1,

3} , Adam Matěj _{1,

2} , Mikulas Matoušek ₄ , Pingo Mutombo ₂ , Jiri Brabec ₄ , Libor Veis ₄ , Timothée Cadart ₅ , Martin Kotora ₅ , Pavel Jelínek _{1,

2}

Affiliation

The synthesis of polycyclic aromatic hydrocarbons containing various non-benzenoid rings remains a big challenge facing contemporary organic chemistry despite a considerable effort made over the last decades. Herein, we present a novel route, employing on-surface chemistry, to synthesize nonalternant polycyclic aromatic hydrocarbons containing up to four distinct kinds of non-benzenoid rings. We show that the surface-induced mechanical constraints imposed on strained helical reactants play a decisive role leading to the formation of products, energetically unfavorable in solution, with a peculiar ring current stabilizing the aromatic character of the π-conjugated system. Determination of the chemical and electronic structures of the most frequent product reveals its closed-shell character and low band gap. The present study renders a new route for the synthesis of novel nonalternant polycyclic aromatic hydrocarbons or other hydrocarbons driven by internal stress imposed by the surface not available by traditional approaches of organic chemistry in solution.

中文翻译：

含有四至八元环的非交替非苯类芳族化合物的表面应变驱动合成

尽管在过去的几十年里做出了相当大的努力，但含有各种非苯环的多环芳烃的合成仍然是当代有机化学面临的一大挑战。在此，我们提出了一种采用表面化学的新途径来合成包含多达四种不同类型的非苯环的非交替多环芳烃。我们表明，对应变螺旋反应物施加的表面诱导机械约束起着决定性作用，导致产物的形成，在溶液中能量不利，具有稳定 π 共轭体系的芳香特性的特殊环电流。最常见产品的化学和电子结构的测定揭示了其闭壳特性和低带隙。

更新日期：2021-09-15

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