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Novel synthetic strategy towards subphthalocyanine-functionalized acetylenic scaffolds via various dibromo-enynes.
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2020-06-30 , DOI: 10.1039/d0ob00988a
Line Broløs 1 , Martin Drøhse Kilde 1 , Mogens Brøndsted Nielsen 1
Affiliation  

Boron subphthalocyanine (SubPc) is a strong chromophore with interesting applications in the field of functional materials and can be synthetically modified in both the peripheral and axial positions, allowing tuning of optical and redox properties. Herein we present novel acetylenic scaffolds where SubPc units are bridged via acetylenic moieties at the boron atoms. Specifically, we show that dibromo-functionalized enyne and enediyne units (vinylic dibromides) can be attached to one or two SubPc boron atoms using an AlCl3-mediated alkynylation protocol of trimethylsilyl-protected alkynes, and such compounds can conveniently be employed for further Sonogashira or Glaser–Hay coupling reactions. Thereby, new tetraethynylethene (TEE) – SubPc scaffolds were obtained. The degree of communication between two SubPc units incorporated in dimeric scaffolds was investigated by cyclic voltammetry. When bridged by one TEE unit, the oxidations of the SubPc units occurred sequentially, while the two SubPc units behaved as independent redox centers when separated by two TEE units.

中文翻译:

通过各种二溴烯炔制备亚酞菁功能化炔类支架的新合成策略。

硼亚酞菁 (SubPc) 是一种强生色团,在功能材料领域具有有趣的应用,可以在周边和轴向位置进行合成修饰,从而可以调节光学和氧化还原特性。在这里,我们提出了新的炔属支架,其中 SubPc 单元通过硼原子上的炔属部分桥接。具体来说,我们表明二溴官能化的烯炔和烯二炔单元(乙烯基二溴化物)可以使用 AlCl 3连接到一个或两个 SubPc 硼原子介导的三甲基甲硅烷基保护的炔烃的炔基化方案,这些化合物可以方便地用于进一步的 Sonogashira 或 Glaser-Hay 偶联反应。因此,获得了新的四乙炔基乙烯 (TEE) - SubPc 支架。通过循环伏安法研究了并入二聚体支架中的两个 SubPc 单元之间的通信程度。当被一个 TEE 单元桥接时,SubPc 单元的氧化顺序发生,而两个 SubPc 单元在被两个 TEE 单元隔开时表现为独立的氧化还原中心。
更新日期:2020-08-12
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