C3-symmetrical self-assembled structures investigated by vibrational circular dichroism

M.M.J. Smulders, T. Buffeteau, D. Cavagnat, M. Wolffs, A.P.H.J. Schenning, E.W. Meijer

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Abstract

We demonstrate by using vibrational circular dichroism (VCD) spectroscopy that it is possible to investigate the chirality of a supramolecular polymeric system in relatively dilute solutions. Chiral C3-symmetrical discotic molecules, based on a trialkylbenzene-1,3,5-carboxamide, form supramolecular columnar stacks with a right-handed helical structure in solution due to intermolecular hydrogen bonds. The handedness of the supramolecular chirality is determined using electronic spectroscopy measurements. Under dilute conditions (at 10-3 M concentrations), it was also possible to probe the hydrogen bonding moieties with IR and VCD spectroscopy on these self-assembled structures. In combination with density functional theory (DFT) calculations, we could verify the preference for a right-handed chirality in the helical stacks and the nonplanar orientation of the carbonyl groups present in the molecule. This chiral arrangement is in agreement with the structure determined for a related benzene-1,3,5-tricarboxamide by X-ray diffraction. Chirality, 2008.
Original languageEnglish
Pages (from-to)1016-1022
JournalChirality
Volume20
Issue number9
DOIs
Publication statusPublished - 2008

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