Novel freebase and zinc bilinone dimers with optically active peripheral groups. Synthesis and application to chiral nematic induction in a nematic mesophase

Novel freebase and zinc bilinone dimers with optically active peripheral groups. Synthesis and... In order to investigate effective dopants to induce chiral nematic liquid crystalline phases, novel freebase (FbBL) and zinc bilinone (ZnBL) derivatives bearing optically active aliphatic groups ((S)-3,7-dimethyloctyls) at the peripheral positions were prepared. From the CD spectra, it was confirmed that M-helicity in the bilinone frameworks was modestly enriched for ZnBLs, whereas helicity was hardly induced for FbBLs except for the o-xylylene-spaced dimer. When N-(4-methoxybenzylidene)-4-butylaniline (MBBA) was doped with the bilinone derivatives, the chiral nematic phase was effectively induced, and the helical twisting powers (βMs) ranged from −95 to −159 μm−1. The control experiment using (S)-3,7-dimethyl-1-phenyloctane (βM = +14 μm−1) clearly showed that the induced chiral helical frameworks of FbBL and ZnBL predominantly contribute to chiral nematic induction of MBBA. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Novel freebase and zinc bilinone dimers with optically active peripheral groups. Synthesis and application to chiral nematic induction in a nematic mesophase

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Publisher
Springer Netherlands
Copyright
Copyright © 2009 by Springer Science+Business Media BV
Subject
Chemistry; Inorganic Chemistry ; Physical Chemistry ; Catalysis
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-009-0078-9
Publisher site
See Article on Publisher Site

Abstract

In order to investigate effective dopants to induce chiral nematic liquid crystalline phases, novel freebase (FbBL) and zinc bilinone (ZnBL) derivatives bearing optically active aliphatic groups ((S)-3,7-dimethyloctyls) at the peripheral positions were prepared. From the CD spectra, it was confirmed that M-helicity in the bilinone frameworks was modestly enriched for ZnBLs, whereas helicity was hardly induced for FbBLs except for the o-xylylene-spaced dimer. When N-(4-methoxybenzylidene)-4-butylaniline (MBBA) was doped with the bilinone derivatives, the chiral nematic phase was effectively induced, and the helical twisting powers (βMs) ranged from −95 to −159 μm−1. The control experiment using (S)-3,7-dimethyl-1-phenyloctane (βM = +14 μm−1) clearly showed that the induced chiral helical frameworks of FbBL and ZnBL predominantly contribute to chiral nematic induction of MBBA.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Oct 10, 2009

References

  • First enantioselective catalysis using a helical diphosphane
    Reetz, MT; Beuttenmüller, EW; Goddard, R
  • Kinetic resolution in Pd-catalyzed allylic substitution using the PHelix ligand
    Reetz, MT; Sostmann, S
  • A new helicopodand: molecular recognition of dicarboxylic acids with high diastereoselectivity
    Owens, L; Thilgen, C; Diederich, F; Knobler, CB

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