Synthesis and mesomorphism of modified 2,5-Di(4-dodecoxyphen-1-yl)-c-cyclopentene-pyridines

ABSTRACT

Herein, we report on a new series of mesomorphic compounds synthesised by directional functionalisation of 2,5-di(4-dodecoxyphen-1-yl-c-cyclopentene-pyridine) on the c-cyclopentene moiety. The first functionalisation of the starting compound gave rise to a racemic product modified with a hydroxyl group on the fused cyclopentene ring. Further oxidation of this alcohol to a prochiral ketone and subsequent enantioselective reduction back to the alcohol afforded a new chiral alcohol. Further, the hydroxyl group of the chiral alcohol could be substituted by fluorine in a S_N2 reaction, leading to a chiral compound with enantiomeric excess (ee) of 66% and chiral nematic liquid-crystalline (LC) phase.

GRAPHICAL ABSTRACT

KEYWORDS:

• Phenylpyridines
• chirality
• nematics
• mesomorphism

Acknowledgements

The authors thank Richard Taylor (York) for helpful discussions and Stephen Cowling (York) for measurements of helical pitch.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was supported by Ministry of Education and Science of the Russian Federation (state task 4.1626.2014/K) and the Royal Society for the Joint Project Grant [IE121115].