Preparation of a Rigid and Nearly Coplanar Bis-tetracene Dimer through an Application of the CANAL Reaction,The Journal of Organic Chemistry

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Preparation of a Rigid and Nearly Coplanar Bis-tetracene Dimer through an Application of the CANAL Reaction
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-08-22 , DOI: 10.1021/acs.joc.3c00809
Ethan G Miller ₁ , Madhu Singh ₁ , Sean Parkin ₂ , Tarek Sammakia ₁ , Niels H Damrauer _{1,

3}

Affiliation

A rigid tetracene dimer with a substantial interchromophore distance has been prepared through an application of the recently developed catalytic arene-norbornene annulation (CANAL) reaction. An iterative cycloaddition route was found to be unsuccessful, so a shorter route was adopted whereby fragments were coupled in the penultimate step to form a 13:1 mixture of two diastereomers, the major of which was isolated and crystallized. Constituent tetracene moieties are linked with a rigid, well-defined bridge and feature a near-co-planar mutual orientation of the acenes.

中文翻译：

应用 CANAL 反应制备刚性且几乎共面的双四苯二聚体

通过应用最近开发的催化芳烃-降冰片烯成环（CANAL）反应，制备了具有显着发色团间距离的刚性并四苯二聚体。发现迭代环加成路线不成功，因此采用了更短的路线，即在倒数第二步中将片段偶联，形成两种非对映异构体的 13:1 混合物，其中主要部分被分离并结晶。并四苯的组成部分通过刚性、明确的桥连接，并具有接近共面的并苯相互取向。

更新日期：2023-08-22

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