<p>Two series of new hydroxy tail-terminated cyanobiphenyl compounds are described. The 4′-ω-hydroxyalkynyl-4-cyanobiphenyl compounds (<b>1a</b>–<b>1g</b>) were synthesised as the key intermediates to the 4′-?ω-hydroxyalkyl-4-cyanobiphenyl compounds (<b>2a</b>–<b>2g</b>) obtained upon reduction of the acetylenes. Many of these ω-hydroxyalkynyl and ω-hydroxyalkyl cyanobiphenyl compounds exhibit nematic mesophases and they also serve as precursors for the synthesis of other interesting materials. Using density functional theory, we calculate the dipole moment of all relevant ω-hydroxyalkynyl and ω-hydroxyalkyl cyanobiphenyl compounds and find a correlation between the calculated dipole moments and measured crystalline to nematic or isotropic liquid transition temperatures.</p
