Benzo-Fused Double [7]Carbohelicene: Synthesis, Structures, and Physicochemical Properties

Yunbin Hu1, Xiao-Ye Wang1, Pi-Xian Peng2

  • 1Max Planck Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany.

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In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
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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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