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Diazulenopentalene: Facile Synthesis of Linear Non-Alternant Molecular Carbons through Pt-Mediated Rearrangement
Zhaohang Lin1, Chang Wang1, Farshad Shiri2
1Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong 999077, China.
Abstract:
Pentalene is a classic 8π antiaromatic non-alternant compound that displays high reactivity. To stabilize pentalene and investigate its properties, benzene rings are typically fused to its core. Advances in metal-catalyzed chemistry have rapidly accelerated the development of pentalene-incorporated molecular carbons. However, fully non-alternant structures based on the pentalene skeleton remain underexplored due to synthetic challenges. Here, we report the synthesis of a novel linear non-alternant hydrocarbon, diazulenopentalene, achieved via a Pt-mediated rearrangement arylation, with the mechanism elucidated by computational studies. Single-crystal analysis, complemented by aromaticity calculations, revealed that diazulenopentalene comprises distinct pentalene and azulene units. The synthetic strategy presented here provides a promising platform for a deeper investigation into this unique linear molecular carbon.
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