Functionalization of Pentacene: A Facile and Versatile Approach to Contorted Polycyclic Aromatic Hydrocarbons |
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Authors: | Meng-Xiang Wu Yantong Li Peipei Liu Xusheng Shi Hao Kang Xiao-Li Zhao Lin Xu Xiaodong Li Junfeng Fang Zhiwei Fang Ya Cheng Huakang Yu Xueliang Shi Hai-Bo Yang |
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Institution: | 1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 P. R. China;2. School of Physics and Optoelectronics, South China University of Technology, Guangzhou, 510640 China;3. School of Physics and Electronic Science, Engineering Research Center of Nanophotonics & Advanced Instrument, Ministry of Education, East China Normal University, Shanghai, 200241 P. R. China;4. State Key Laboratory of Precision Spectroscopy, School of Physics and Electronic Science, East China Normal University, Shanghai, 200241 P. R. China |
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Abstract: | In this work, a facile and versatile strategy for the synthesis of contorted polycyclic aromatic hydrocarbons (PAHs) starting from the functionalized pentacene was established. A series of novel PAHs 1 – 4 and their derivatives were synthesized through a simple two-step synthesis procedure involving an intramolecular reductive Friedel–Crafts cyclization of four newly synthesized pentacene aldehydes 5 – 8 as a key step. All the molecules were confirmed by single-crystal X-ray diffraction and their photophysical and electrochemical properties were studied in detail. Interestingly, the most striking feature of 1 – 4 is their highly contorted carbon structures and the accompanying helical chirality. In particular, the optical resolution of 2 was successfully achieved by chiral-phase HPLC, and the enantiomers were characterized by circular dichroism and circularly polarized luminescence spectroscopy. Despite the highly nonplanar conformations, these contorted PAHs exhibited emissive properties with moderate-to-good fluorescence quantum yields, implying the potential utility of this series PAHs as high-quality organic laser dyes. By using a self-assembly method with the help of epoxy resin, a bottle microlaser based on 3 a was successfully illustrated with a lasing wavelength of 567.8 nm at a threshold of 0.3 mJ/cm2. We believe that this work will shed light on the chemical versatility of pentacene and its derivatives in the construction of novel functionalized PAHs. |
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Keywords: | Chiroptical Properties Optical Resolution Organic Laser Polycyclic Aromatic Hydrocarbons (PAHs) X-Ray Diffraction |
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