An approach to helical tubular self-aggregation using C2-symmetric self-complementary hydrogen-bonding cavity molecules

被引:57
作者
Stoncius, Sigitas
Orentas, Edvinas
Butkus, Eugenius
Ohrstrom, Lars
Wendt, Ola F.
Warnmark, Kenneth
机构
[1] Vilnius State Univ, Dept Organ Chem, LT-03225 Vilnius, Lithuania
[2] Chalmers Univ Technol, Dept Chem & Biol Engn, SE-41296 Gothenburg, Sweden
[3] Lund Univ, Dept Chem, SE-22100 Lund, Sweden
关键词
D O I
10.1021/ja061160z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In an approach to helical self-aggregation, C-2-symmetric cavity compounds based on the fusion of the bicyclo[3.3.1] nonane and indole framework and incorporating two 2-pyridone hydrogen-bonding motifs, compounds (-)-4 (pyrrole N-butyl) and (-)-5 (pyrrole N-decyl), have been synthesized. The 2-pyridone AD-DA hydrogen-bonding motif failed to operate in the solid state as demonstrated by X-ray diffraction analysis of (-)-4. Instead, the hydrogen- bonded (D-A) chains center dot center dot center dot O=C-N-H center dot center dot center dot O=C-N-H center dot center dot center dot O=C-N-H center dot center dot center dot, interconnecting columnar stacks, comprise helices of the right-handed (P) chirality motif. In solution, the aggregation of (-)-5 was studied by NMR, electronic, and CD spectroscopies, and VPO measurements. These investigations strongly suggest that (-)-5 associates to oligomers in CHCl3 and CH2Cl2 using the 2-pyridone motif, fitting the equal K model, and that pi-stacking can be ruled out as a mode of aggregation. We conclude that the so formed aggregates of (-)-5 have a helical structure, based on the fact that only helical tubular structures can result when enantiomerically pure 5 uses its 2-pyridone AD-DA hydrogenbonding motifs for aggregation.
引用
收藏
页码:8272 / 8285
页数:14
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