Synthesis and Recognition Properties of Aromatic Amide Oligomers: Molecular Zippers

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• 作者：Adrian P. Bisson ; Fiona J. Carver ; Drake S. Eggleston ; R. Curtis Haltiwanger ; Christopher A. Hunter ; David L. Livingstone ; James F. McCabe ; Carmen Rotger ; and Alan E. Rowan
• 刊名：Journal of the American Chemical Society
• 出版年：2000
• 出版时间：September 20, 2000
• 年：2000
• 卷：122
• 期：37
• 页码：8856 - 8868
• 全文大小：417K
• 年卷期：v.122,no.37(September 20, 2000)
• ISSN：1520-5126

文摘

A series of amide oligomers have been prepared from isophthalic acid and a bisaniline derivative.These compounds assemble into double-stranded zipper complexes in solution via hydrogen-bonding and edge-to-face aromatic interactions. The stability and structures of the complexes have been determined by ¹H NMRspectroscopy in chloroform solution. The stability of the complexes increases with increasing chain length,indicating cooperativity between the individual recognition sites in the oligomers. Oligomers which arecomplementary form more stable complexes than non-complementary systems with overhanging ends. Additionof polar solvents such as methanol destabilizes the complexes, because it competes for hydrogen-bondinginteractions which appear to be the main driving force for binding in this system.