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

• DOI: 10.1021/jo702046f
• Publication Date: 2008-01-31T11:21:22Z
• Authors: Yuan-Yuan Zhu; Chuang Li; Guang-Yu Li; Xi-Kui Jiang; Zhan-Ting Li
• Keywords: Coronene; Pyridazine; Amide

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