Bis-corannulenoanthracene: An Angularly Fused Pentacene as a Precursor for Barrelene-Tethered Receptors for Fullerenes

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• 作者：K. G. Upul R. Kumarasinghe ; Frank R. Fronczek ; Henry U. Valle ; Andrzej Sygula
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：18
• 期：13
• 页码：3054-3057
• 全文大小：315K
• 年卷期：0
• ISSN：1523-7052

文摘

Bis-corannulenoanthracene (C₅₀H₂₂, 5) was prepared by the Diels–Alder double cycloaddition of isocorannulenofuran with “bis-benzyne”, followed by deoxygenation of the adducts. Despite the presence of a pentacene core, 5 is stable enough to be isolated and stored. A cycloaddition reaction of 5 with maleic anhydride produces 10 which exhibits strong affinity toward C₆₀, as evidenced by ¹H NMR titration experiment. Synthesis of 10 demonstrates the synthetic utility of hydrocarbon 5 in the preparation of the barrelene-based molecular clips with two benzocorannulene pincers adorned with polar substituents on their tethers, which will allow for immobilization of the receptors on solid supports.