Syntheses and Structures of Functionalized [9]Cycloparaphenylenes as Carbon Nanohoops Bearing Carbomethoxy and N-Phenylphthalimido Groups

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• 作者：Shuangjiang Li ; Changfeng Huang ; Haresh Thakellapalli ; Behzad Farajidizaji ; Brian V. Popp ; Jeffrey L. Petersen ; Kung K. Wang
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：18
• 期：9
• 页码：2268-2271
• 全文大小：424K
• 年卷期：0
• ISSN：1523-7052

文摘

Functionalized [9]cycloparaphenylenes ([9]CPPs) bearing nine aromatic units in the macrocyclic structures were synthesized. The macrocyclic structures were substituted with carbomethoxy or N-phenylphthalimido groups. The Diels–Alder reaction of (E,E)-1,4-bis(4-bromophenyl)-1,3-butadiene or a related diene with dimethyl acetylenedicarboxylate followed by the nickel-mediated homocoupling reactions and oxidative aromatization produced the functionalized [9]CPPs. Treatment of a resultant [9]CPP with aniline or 1,4-diaminobenzene gave the corresponding N-phenylphthalimides. The X-ray structure of a [9]CPP bearing six carbomethoxy groups was obtained.