Rational design and synthesis of a novel laterally-tetrafluorinated tricyclic mesogen with large negative dielectric anisotropy

Organic & Biomolecular Chemistry
Shigeyuki YamadaTsutomu Konno

Abstract

Guided by theoretical calculations, we predicted that 5,5,6,6-tetrafluoro-1-methoxycyclohex-1-ene, a new structural motif, exhibits a large negative dielectric anisotropy, and then developed a synthetic strategy for the preparation of the novel tetrafluorinated tricyclic mesogen in twelve reaction steps starting from a commercially available fluorinated starting material. During the evaluation of its liquid-crystalline characteristics, the tetrafluorinated mesogen was found to display low birefringence and a large negative dielectric anisotropy, confirming that its molecular structure is a reasonable design for the further development of novel mesogenic molecules with large negative dielectric anisotropies.

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Methods Mentioned

BETA
optical
differential scanning calorimetry
NMR
column chromatography
silica gel column chromatography
silica-gel column chromatography

Software Mentioned

Gaussian

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