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 C(3)-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. (c) 2008 Wiley-Liss, Inc.
journal_name
Chiralityjournal_title
Chiralityauthors
Smulders MM,Buffeteau T,Cavagnat D,Wolffs M,Schenning AP,Meijer EWdoi
10.1002/chir.20568subject
Has Abstractpub_date
2008-09-01 00:00:00pages
1016-22issue
9eissn
0899-0042issn
1520-636Xjournal_volume
20pub_type
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