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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Published inJournal of organic chemistry Vol. 86; no. 21; pp. 14398 - 14403
Main Authors Ahmad, Ishfaq, Kim, Dongwook, Kodirov, Rukhillo, Yu, Soo-Young, Seo, Jeong-Min, Mahmood, Javeed, Baek, Jong-Beom
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.11.2021
Amer Chemical Soc
Subjects
bromination
catalytic activity
Chemistry
Chemistry, Organic
materials science
organic chemistry
Physical Sciences
Science & Technology
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ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/acs.joc.1c01127

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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.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.1c01127