Synthesis of a Dicyclohepta[a,g]heptalene-Containing Polycyclic Conjugated Hydrocarbon and the Impact of Non-Alternant Topologies |
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Authors: | Junting Wang Fernando Gordillo Gámez Jose Marín-Beloqui Aitor Diaz-Andres Dr Xiaohe Miao Prof David Casanova Prof Juan Casado Dr Junzhi Liu |
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Institution: | 1. Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China;2. Department of Physical Chemistry, University of Malaga, Campus de Teations s/n, 229071 Malaga, Spain;3. Donostia International Physics Center (DIPC), 20018 Donostia, Euskadi, Spain;4. Instrumentation and Service Center for Physical Sciences, Westlake University, Hangzhou, 310024, Zhejiang Province China;5. Donostia International Physics Center (DIPC), 20018 Donostia, Euskadi, Spain
IKERBASQUE—Basque Foundation for Science, 48009 Bilbao, Euskadi, Spain |
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Abstract: | Incorporating non-hexagonal rings into polycyclic conjugated hydrocarbons (PCHs) can significantly affect their electronic and optoelectronic properties and chemical reactivities. Here, we report the first bottom-up synthesis of a dicycloheptaa,g]heptalene-embedded PCH ( 1 ) with four continuous heptagons, which are arranged in a “Z” shape. Compared with its structural isomer bischrysene 1 R with only hexagonal rings, compound 1 presents a distinct antiaromatic character, especially the inner heptalene core, which possesses clear antiaromatic nature. In addition, PCH 1 exhibits a narrower highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy gap than its benzenoid contrast 1 R , as verified by experimental measurements and theoretical calculations. Our work reported herein not only provides a new way to synthesize novel PCHs with non-alternant topologies but also offers the possibility to tune their electronic and optical properties. |
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Keywords: | Antiaromaticity Four Contiguous Heptagons Non-Alternant Topology Polycyclic Conjugated Hydrocarbons (PCHs) |
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