Synthesis of Tetraaza[8]circulenes

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  • Published: 15 May 2017
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Organic Letters/ACS Publications
thumbnail image: Synthesis of Tetraaza[8]circulenes

[8]Circulenes are macrocycles with an eight-membered "core". Incorporating heterocycles such as pyrroles into this class of compounds could make them useful for optical and electronic applications. However, tetraaza[8]circulenes with four nitrogen atoms had so far been limited to one example with four benzene substituents [1].

Yoshihiro Miyake and colleagues, Nagoya University, Japan, and colleagues have developed a synthesis approach for tetraaza[8]circulenes (pictured) with different substituents. The team first synthesized the corresponding tetrathia[8]circulenes, which were then oxidized using m-chloroperoxybenzoic acid (mCPBA). The resulting octaoxide was subjected to a nucleophilic aromatic substitution reaction in which amines replace the sulfur groups.

The resulting tetraaza[8]circulenes exhibit bright fluorescence both in solution and in the solid state. The team is also working on using the compounds as p-type semiconductors. According to the researchers, this approach could be useful for the synthesis of other hetero[8]circulenes with tunable optical and electronic properties.



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