A Dipleiadiene‐Embedded Aromatic Saddle Consisting of 86 Carbon Atoms |
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Authors: | Sai Ho Pun Chi Kit Chan Dr. Jiye Luo Prof. Zhifeng Liu Prof. Qian Miao |
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Affiliation: | 1. Department of Chemistry, The Chinese University of Hong Kong, New Territories, Hong Kong, China;2. School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, Guangdong, China |
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Abstract: | This study presents a new type of negatively curved nanographene (C86H32) that contains an unprecedented pattern of heptagons. A tert‐butylated derivative of C86H32 was successfully synthesized using tetrabenzodipleiadiene as a key building block. This synthesis involved a ring expansion reaction as a key step to form the seven‐membered rings in the framework of tetrabenzodipleiadiene. The single‐crystal structure reveals a saddle‐shaped molecule with a highly bent naphthalene moiety at the center of the polycyclic backbone. As found from the DFT calculations, this aromatic saddle is flexible at room temperature and has a saddle‐shaped geometry as the dominant conformation. The DFT calculations along with experimental results show that the attachment of t‐butyl groups to the central tetrabenzodipleiadiene moiety of nanographene C86H32 can stabilize the saddle conformation and make this nanographene less flexible. |
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Keywords: | arenes nanographene polycycles stereochemistry |
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