Effect of including extra phenylazo moiety on the mesophase behaviour of three-ring azo/ester molecules

ABSTRACT

Five homologous series of the four-ring 4-substituted phenylazo phenyl 4ʹ-(4ʹ-alkoxy phenylazo) benzoates (In_a–e) were prepared and their mesophase behaviour investigated by differential scanning calorimetry (DSC) and phases identified by polarised light microscopy (PLM). Compounds prepared were structurally characterised via infrared, ¹H-NMR, mass spectroscopy, thermogravimetric and elemental analysis. Transition temperatures were first correlated with the alkoxy-chain length (n, that varies between 6, 8, 10, 14, and 16 carbons) within each homologous series, and again with the polarisability anisotropy (Δα_X) of the Ar-X bond, where X changes between CH₃O, CH₃, H, Br, and CN groups . Comparative studies were made to investigate the effect of introducing the extra phenyl azo moiety into the previously investigated three-ring compounds, 4-substituted phenyl 4′-(4″-alkoxyphenylazo) benzoates (IIn_a–e), 4-substituted phenylazo 4′-(4″- alkoxy phenyl) benzoates (IIIn_a–e), and 4-(4′-alkoxy phenylazo) phenyl 4″-substituted benzoates (IVn_a–e), each bear the same polar group, X, and the alkoxy group, n .

Graphical Abstract

KEYWORDS:

• Azo-ester
• four rings
• polar substituents
• mesophase stability

Disclosure statement

No potential conflict of interest was reported by the authors.