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Updated: Sep 9, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.6K

ビフェニレンとブタディーネの抗芳香性ユニットから成るマクロサイクル

Shoko Nagayama1, Hiroki Kawakatsu1, Daisuke Asai1

  • 1Department of Applied Chemistry, School of Science and Technology, Meiji University 1-1-1 Higashimita, Tama-ku Kawasaki Kanagawa 214-8571 Japan tahara@meiji.ac.jp.

Chemical science
|September 2, 2025
PubMed
まとめ

研究者は,ビフェニレンとブタジーン単位を使用して,大きなπ結合マクロサイクルを合成した. これらのマクロサイクルは赤色発光を示し,オーダーされたネットワークを形成し,独特の電子特性を発揮し,抗芳香化合物の設計を進めています.

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Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
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