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Beilstein J Org Chem. 2012;8:155-63. doi: 10.3762/bjoc.8.16. Epub 2012 Jan 24.

The interplay of configuration and conformation in helical perylenequinones: Insights from chirality induction in liquid crystals and calculations.

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  • 1Department of Chemical Sciences, University of Padova, via Marzolo 1, 35131 Padova, Italy.

Abstract

The chirality transfer in liquid crystals induced by two helical perylenequinones (namely, the natural compounds cercosporin and phleichrome) was investigated by integrating measurements of helical twisting power with a conformational analysis by DFT calculations and with the prediction of their twisting ability by the surface-chirality method. The two quasi-enantiomeric derivatives induce oppositely handed cholesteric phases when introduced as dopants in nematic solvents. We evaluated the role of the different conformations of the chiral hydroxyalkyl side chains in determining the helical twisting power: They were found to affect the strength of the chirality transfer, although the handedness of the induced cholesteric phase is essentially determined by the axial chirality (helicity) of the core of the perylenequinones.

KEYWORDS:

DFT calculations; chirality; conformational analysis; helical twisting power; nematic liquid crystals

PMID:
22423282
[PubMed]
PMCID:
PMC3302075
Free PMC Article

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