An approach to helical tubular self-aggregation using C-2-symmetric self-complementary hydrogen-bonding cavity molecules
Journal article, 2006

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 ⋯O=C-N-H⋯O=C-N-H⋯O=C-N- H⋯, 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 CHCl 3 and CH 2 Cl 2 using the 2-pyridone motif, fitting the equal K model, and that π-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 hydrogen-bonding motifs for aggregation. © 2006 American Chemical Society.


S. Stoncius

Vilnius University

E. Orentas

Vilnius University

E. Butkus

Vilnius University

Lars Öhrström

Chalmers, Chemical and Biological Engineering, Physical Chemistry

O. F. Wendt

Lund University

K. Warnmark

Lund University

Journal of the American Chemical Society

0002-7863 (ISSN) 1520-5126 (eISSN)

Vol. 128 25 8272-8285

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