Alternating 2,6-/3,5-Substituted Pyridine-Acetylene Macrocycles: π-Stacking Self-Assemblies Enhanced by Intermolecular Dipole–Dipole Interaction

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• 作者：Hajime Abe ; Kohei Ohtani ; Daiki Suzuki ; Yusuke Chida ; Yuta Shimada ; Shinya Matsumoto ; Masahiko Inouye
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：February 7, 2014
• 年：2014
• 卷：16
• 期：3
• 页码：828-831
• 全文大小：310K
• ISSN：1523-7052

文摘

Macrocyclic compounds consisting of three 2,6-pyridylene and three 3,5-pyridylene units linked by acetylene bonds were synthesized by a Sonogashira reaction. The X-ray structures showed 蟺-stacked pairs of two macrocycles, in which a 2,6-pyridylene unit of the one molecule overlaps a 3,5-pyridylene of the other molecule because of dipole鈥揹ipole interaction. Atomic force microscope (AFM) measurements revealed fibril structures indicating the stacking of the rigid planar macrocycles. Hydrogen-bonding ability of the macrocyclic inside was demonstrated by the addition of octyl 尾-d-glucopyranoside.