Hydrogen-Bonded Aryl Amide Macrocycles: Synthesis, Single-Crystal Structures, and Stacking Interactions with Fullerenes and Coronene

详细信息    查看全文

• 作者：Yuan-Yuan Zhu ; Chuang Li ; Guang-Yu Li ; Xi-Kui Jiang ; Zhan-Ting Li
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：March 7, 2008
• 年：2008
• 卷：73
• 期：5
• 页码：1745 - 1751
• 全文大小：266K
• 年卷期：v.73,no.5(March 7, 2008)
• ISSN：1520-6904

文摘

ournals/joceah/73/i05/figures/jo702046fn00001.gif" ALIGN="left" HSPACE=5>

Six hydrogen-bonded shape-persistent aryl amide macrocycles have been prepared by using one-stepand (for some) step-by-step approaches. From the one-step reactions, 3 + 3, 2 + 2, or even 1 + 1macrocycles were obtained in modest to good yields. The reaction selectivity was highly dependent onthe structures of the precursors. The X-ray structural analysis of two methoxyl-bearing macrocycles revealedintramolecular hydrogen bonding and weak intermolecular stacking interaction; no column-styled stackingstructures were observed. The ¹H (DOSY) NMR, UV-vis, and fluorescent experiments indicated thatthe new rigidified macrocycles complex fullerenes or coronene in chloroform through intermolecular-stacking interaction. The association constants of the corresponding 1:1 complexes have been determinedif the stacking was able to cause important fluorescent quenching of the macrocycles or coronene.