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

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.