Synthesis of Saddle-Shape Octaaminotetraphenylene Octahydrochloride

Apart from being experimentally and theoretically interesting, tetraphenylene has potential applications in different fields, including supramolecular chemistry, material science, and asymmetric catalysis. Although a wide range of substituted tetraphenylenes have been reported, octaamine-based tetra...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-11, Vol.86 (21), p.14398-14403
Main Authors: Ahmad, Ishfaq, Kim, Dongwook, Kodirov, Rukhillo, Yu, Soo-Young, Seo, Jeong-Min, Mahmood, Javeed, Baek, Jong-Beom
Format: Article
Language:English
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Summary:Apart from being experimentally and theoretically interesting, tetraphenylene has potential applications in different fields, including supramolecular chemistry, material science, and asymmetric catalysis. Although a wide range of substituted tetraphenylenes have been reported, octaamine-based tetraphenylene derivatives have not been reported because of their instability. Here, stable octaaminotetraphenylene octahydrochloride is synthesized from the bromination of tetraphenylene to octabromotetraphenylene, which is subsequently aminated into octaiminotetraphenylene. Finally, the imino derivative is deprotected to yield octaaminotetraphenylene octahydrochloride.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01127