Author： McCubbin Adam Snieckus Victor Lemieux Robert
Publisher： Taylor & Francis Ltd
ISSN： 0267-8292
Source： Liquid Crystals, Vol.32, Iss.9, 2005-09, pp. : 1195-1203
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Abstract
The chiral fluorenone mesogens ( R )‐1‐fluoro‐2‐(2‐octyloxy)‐7‐(4‐undecyloxybenzoyloxy)fluoren‐9‐one (2) and ( R )‐2‐(2‐octyloxy)‐7‐(4‐undecyloxybenzoyloxy)‐3‐azafluoren‐9‐one (3) were synthesized using a combined ortho ‐directed and remote metalation strategy, which also incorporates a Suzuki–Miyaura crosscoupling step. These compounds form chiral SmC* liquid crystal phases with reduced polarizations (P o ) of +475 and +332 nC cm −2 at 10 K below the Curie point, respectively. These values are considerably larger than that previously reported for the unsubstituted fluorenone ( R )‐2‐(2‐octyloxy)‐7‐(4‐undecyloxybenzoyloxy)fluoren‐9‐one (1), which is +111 nC cm −2 at 10 K below the Curie point. Molecular modelling based on the Boulder model suggests that the larger polarizations result from a conformational bias of the fluorenone core dipole moment along the polar axis of the SmC* phase caused by stereo‐polar coupling with the chiral 2‐octyloxy side chain.
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