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Rapid Construction of Fold-Line-Shaped BN-Embedded Polycyclic Aromatic Compounds through Diels–Alder Reaction

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journal contribution
posted on 06.12.2019, 14:39 authored by Peng-Fei Zhang, Fang-Dong Zhuang, Ze-Hao Sun, Yang Lu, Jie-Yu Wang, Jian Pei
The Diels–Alder reaction strategy that can rapidly extend the conjugated backbone was applied to facilely synthesize fold-line, coplanar BN-embedded polycyclic aromatic hydrocarbons from simple small BN compounds. The molecular structures and packing modes of these BN-embedded acenes were confirmed by single-crystal X-ray diffraction. Their electronic and photophysical properties were studied by using UV–vis, fluorescence spectroscopy, electrochemical cyclic voltammetry, and density functional theory calculations. These results demonstrate the efficiency and feasibility of this synthetic strategy.