Rapid Construction of Fold-Line-Shaped BN-Embedded Polycyclic Aromatic Compounds through Diels-Alder Reaction
Peng-Fei Zhang1, Fang-Dong Zhuang1, Ze-Hao Sun1
1Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.
Abstract:
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.
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