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Ni(COD)2 coupling of 3,6-dibromocarbazoles as a route to all-carbazole shape persistent macrocycles
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2015-09-09 13:38:57
Leah S. Coumont, Jonathan G.C. Veinot

The number of applications for carbon-based materials has experienced tremendous growth over the last decade arising from their low toxicity, straight-forward chemical modification, and interesting electronic properties. Among these materials, self-assembled structures based on shape persistent macrocycles are perhaps the most exciting as they offer a means to prepare a wide range of morphologies through reversible assembly of these molecular precursors. In this letter, we report on the preparation of a novel family of all-carbazole shape persistent macrocycles through the simple single-step reaction of the corresponding 3,6-dibromocarbazoles over Ni(COD)2. The resultant macrocycles display optical properties characteristic of the parent N-alkyl polycarbazoles, with quantum yields ranging from 11% up to 21% suggesting that certain substituents induce the formation of highly emissive aggregates, which could potentially provide a mechanism for the preparation of functional self-assembled nanomaterials.

中文翻译:

3,6-二溴咔唑的Ni(COD)2偶联作为通向全部咔唑形状的持久性大环化合物的途径

在过去的十年中,基于碳的材料的低毒性,直接的化学修饰和令人感兴趣的电子特性,使应用的数量得到了飞速增长。在这些材料中,基于形状持久性大环的自组装结构可能是最令人兴奋的,因为它们提供了通过这些分子前体的可逆组装来​​制备各种形态的手段。在这封信中,我们报告了通过相应的3,6-二溴咔唑在Ni(COD)2上的简单一步反应制备新的全咔唑形状持久大环家族的方法。。所得的大环化合物显示出母体N-烷基聚咔唑的光学特性,其量子产率范围为11%至21%,表明某些取代基可诱导高发射聚集体的形成,这可能为功能性自我制备提供了一种机制。组装的纳米材料。
更新日期:2015-09-10
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