A Double Helicene with Quadruple Indole-Fused Skeleton and Double NBN-Type Cove-Edged Structure

Lingjuan Chen; Jiaqi Dong; Dehui Tan; Jianfeng Wu; Deng-Tao Yang

doi:10.1002/cjoc.202400512

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (23) : 3069 -3074. DOI: 10.1002/cjoc.202400512

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A Double Helicene with Quadruple Indole-Fused Skeleton and Double NBN-Type Cove-Edged Structure

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Abstract

Construction of helicenes by inducing heteroatoms has regarded as an effective strategy to enhance the chiroptical properties. We report a facile synthesis of a multiple helicene based on four indoles with two electron-rich NBN-coved edges. The structure of the NBN-coved multiple helicene was confirmed by single-crystal X-ray diffraction analysis, revealing a twisted double [5]helicene motif with a saddle-shaped skeleton. This NBN-coved helicene showed strong green fluorescence with good photoluminescence quantum yield. Both theoretical calculations and experimental investigation have been exploited to probe the impact of electron-rich NBN units on aromaticity and photophysical properties of the helicene.

Keywords

NBN / Double helicene / Cove-edged / Indole-fused |π-conjugated

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Lingjuan Chen, Jiaqi Dong, Dehui Tan, Jianfeng Wu, Deng-Tao Yang. A Double Helicene with Quadruple Indole-Fused Skeleton and Double NBN-Type Cove-Edged Structure. Chinese Journal of Chemistry, 2024, 42(23): 3069-3074 DOI:10.1002/cjoc.202400512