Hydrogen-bonded aryl amide macrocycles: synthesis, single-crystal structures, and stacking interactions with fullerenes and coronene.
Six hydrogen-bonded shape-persistent aryl amide macrocycles have been prepared by using one-step and (for some) step-by-step approaches. From the one-step reactions, 3 + 3, 2 + 2, or even 1 + 1 macrocycles were obtained in modest to good yields. The reaction selectivity was highly dependent on the structures of the precursors. The X-ray structural analysis of two methoxyl-bearing macrocycles revealed intramolecular hydrogen bonding and weak intermolecular stacking interaction; no column-styled stacking structures were observed. The 1H (DOSY) NMR, UV-vis, and fluorescent experiments indicated that the new rigidified macrocycles complex fullerenes or coronene in chloroform through intermolecular pi-stacking interaction. The association constants of the corresponding 1:1 complexes have been determined if the stacking was able to cause important fluorescent quenching of the macrocycles or coronene.
Zhu
Yuan-Yuan
YY
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Li
Chuang
C
Li
Guang-Yu
GY
Jiang
Xi-Kui
XK
Li
Zhan-Ting
ZT
D000577:Amides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D037741:Fullerenes / Q000737:chemistry*; D006860:Hydrogen Bonding; D047028:Macrocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet
D000577:Amides; D037741:Fullerenes; D047028:Macrocyclic Compounds; D011083:Polycyclic Compounds; C012256:coronene