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

Authors :
Elisa Frezza
Silvia Pieraccini
Stefania Mazzini
Alberta Ferrarini
Gian Piero Spada
Source :
Beilstein Journal of Organic Chemistry, Vol 8, Iss 1, Pp 155-163 (2012)
Publication Year :
2012
Publisher :
Beilstein-Institut, 2012.

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.

Details

Language :
English
ISSN :
18605397
Volume :
8
Issue :
1
Database :
Directory of Open Access Journals
Journal :
Beilstein Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsdoj.86e04dd9d347405499620eea0288fd79
Document Type :
article
Full Text :
https://doi.org/10.3762/bjoc.8.16