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Journal Article

A modular cascade synthetic strategy toward structurally constrained boron-doped polycyclic aromatic hydrocarbons


Feng,  Xinliang       
Department of Synthetic Materials and Functional Devices (SMFD), Max Planck Institute of Microstructure Physics, Max Planck Society;

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Zhang, J.-J., Yang, L., Liu, F., Fu, Y., Liu, J., Popov, A. A., et al. (2021). A modular cascade synthetic strategy toward structurally constrained boron-doped polycyclic aromatic hydrocarbons. Angewandte Chemie International Edition, 60(49), 25695-25700. doi:10.1002/anie.202109840.

Cite as: https://hdl.handle.net/21.11116/0000-0009-A286-8
A novel synthetic strategy was developed for the construction of difficult-to-access structurally constrained boron-doped polycyclic aromatic hydrocarbons (sc-B-PAHs) via a cascade reaction from the readily available ortho-aryl-substituted diarylalkynes. This domino process involves borylative cyclization, 1,4-boron migration and successive two-fold electrophilic borylation. Two types of sc-B-PAHs bearing B-doped [4]helicene (1 a-1 i) or BN-doped [4]helicene (1 n-1 t) and double [4]helicene (1 u-1 v) are constructed by this cascade reaction. Remarkably, this synthetic strategy is characterized by modest yields (20-50 %) and broad substrate scope (18 examples) with versatile functional group tolerance. The resultant sc-B-PAHs show good stability under ambient conditions and are thoroughly investigated by X-ray crystallography, UV/Vis absorption and fluorescence spectroscopy, and cyclic voltammetry. Interestingly enough, BN-doped [4]helicene 1 o forms a unique alternating pi-stacked dimer of enantiomers within a helical columnar superstructure, while BN-doped double [4]helicene 1 u establishes an unprecedented pi-stacked trimeric sandwich structure with a rare 2D lamellar pi-stacking. The synthetic approach reported herein represents a powerful tool for the rapid generation of novel sc-B-PAHs, which are highly attractive for the elucidation of the structure-property relationship and for potential optoelectronic applications.