Functionalized O6–Corona[6]arenes: Synthesis, Structure, and Fullerene Complexation Property

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• 作者：Wen-Sheng Ren ; Liang Zhao ; Mei-Xiang Wang
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：18
• 期：13
• 页码：3126-3129
• 全文大小：340K
• 年卷期：0
• ISSN：1523-7052

文摘

The synthesis, structure, and fullerene complexation property of novel and functionalized O_n–corona[n]arenes were reported. Based on the fragment coupling strategy, ester-containing O_n–corona[n]arenes (n = 6, 8) were obtained readily starting from 1,4-hydroquinone and diethyl 2,5-difluoroterephthalate. Reduction of esters with LiAlH₄ produced almost quantitatively hydroxymethylated O_n–corona[n]arenes, which underwent etherification with MeI to afford methoxymethyl-substituted O_n–corona[n]arenes (n = 6, 8) in good yields. The macrocycles adopt unique corona-type conformation with a large cylindroid cavity. They are strong macrocyclic host molecules to form 1:1 complexes with fullerenes C₆₀ and C₇₀ in toluene with an associate constant up to (1.59 ± 0.04) × 10⁵ M^–1.