Calix[3]carbazole: One-Step Synthesis and Host–Guest Binding

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• 作者：Peng Yang ; Yong Jian ; Xue Zhou ; Gang Li ; Tuo Deng ; Hongyan Shen ; Zhaozheng Yang ; Zhangmin Tian
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：April 1, 2016
• 年：2016
• 卷：81
• 期：7
• 页码：2974-2980
• 全文大小：451K
• ISSN：1520-6904

文摘

The one-step synthetic strategy for the preparation of the hitherto unknown calix[3]carbazole from readily available starting materials is described. Calix[3]carbazole is obtained in 20% yield, and it could selectively bind the N(C₂H₅)₄⁺ cation (tetraethylammonium, TEA) via cation−π interactions. The experimental and modeling results indicate that calix[3]carbazole possesses a larger π-cavity as well as a better chromophoric property than the traditional phenol-based macrocycles, and thus is capable of binding to and optically responding to the relatively large guest TEA.