Method for the Preparation of Derivatives of Heptiptycene: Toward Dual-Cavity Baskets

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• 作者：Keith Hermann ; Stephen Sardini ; Yian Ruan ; Ryan J. Yoder ; Mrinal Chakraborty ; Shubham Vyas ; Christopher M. Hadad ; Jovica D. Badji膰
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：April 5, 2013
• 年：2013
• 卷：78
• 期：7
• 页码：2984-2991
• 全文大小：552K
• 年卷期：v.78,no.7(April 5, 2013)
• ISSN：1520-6904

文摘

We have developed a novel synthetic method that enables the preparation of functional derivatives of heptiptycene, i.e., cavitands with two juxtaposed cavities. The homocoupling of bicyclic dibromoalkenes is promoted by Pd(OAc)₂ (10%) in dioxane (100 掳C) to give cyclotrimers in 27鈥?7% yield under optimized reaction conditions (Ph₃P, K₂CO₃, n-Bu₄NBr, N₂, 4 脜 MS). These dual-cavity baskets show a strong 蟺 鈫?蟺* absorption at 241 nm (蔚 = 939 000 M^鈥? cm^鈥?), along with a subsequent fluorescence emission at 305 nm.