Department of Chemistry, Mississippi State University , Mississippi State, Mississippi 39762, United States.
Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
Org Lett. 2016 Jul 1;18(13):3054-7. doi: 10.1021/acs.orglett.6b01049. Epub 2016 Jun 9.
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 (1)H 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.
双并环戊二烯并蒽（C50H22，5）是通过异环戊二烯呋喃与“双苯炔”的 Diels-Alder 双环加成反应制备的，然后对加合物进行脱氧。尽管存在五并苯核，5 还是足够稳定，可以分离和储存。5 与马来酸酐的环加成反应生成 10，其对 C60 表现出很强的亲和力，这一点可以通过（1）H NMR 滴定实验证明。10 的合成证明了烃 5 在制备基于桶烯的分子夹中的合成实用性，这些分子夹带有两个苯并环戊二烯夹，其在连接体上带有极性取代基，这将允许受体固定在固体载体上。
