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Structures and Properties of Helicenes

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Helicene Chemistry

Abstract

Structural features of helicenes are briefly introduced, and the crystal structures of several helicenes and heterohelicenes are then discussed. Since helicenes are a kind of polycyclic aromatic hydrocarbons with helical chirality, they exhibit specific physical properties and optical properties, especially the excellent luminescent properties. For example, some helicenes display high fluorescence quantum yields in both solution and solid states. The unique helicity of helicenes also makes them show high specific optical rotation, electronic circularly dichroism, and vibrational circular dichroism. Besides, the determination of absolute configuration of optically pure helicenes and the thermal racemization of helicenes are further discussed. Three empirical rules are proposed for the hinderance of racemization. In addition, other related properties of helicenes including the solubility, basicity of azahelicenes, elasticity of thiahelicenes are also introduced. Finally, the preparation and properties of helicenes with charges and open shells, such as radical anions, radical cations, and helicene cations are described.

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  1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China

    Chuan-Feng Chen & Yun Shen

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Chen, CF., Shen, Y. (2017). Structures and Properties of Helicenes. In: Helicene Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-53168-6_2

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