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The preparation and characterization of laterally substituted 4-alkoxy-stilbazoles, 4-alkoxy-benzoic acids, and 4-alkoxy phenols and hydrogen bonded heterodimeric mixtures of these compounds are reported. Lateral substitution has a minimal effect on the ring electronics of 4-alkoxy benzoic acids and 4-alkoxy phenols; however the ring electronics of stilbazole units is extremely sensitive to lateral substitution. While lateral substitution is an effective technique for lowering the melting points of both hydrogen bonded complexes and their individual components, its effect on the electronics of stilbazoles and steric disruption of both intermolecular hydrogen bonding and molecular packing in the solid state disrupts the formation of liquid crystalline phases in both the individual components and hydrogen bonded complexes

Effect of Lateral Substitution on the Electronics and Phase Transitions of Stilbazoles, Benzoic Acids, Phenols, and Hydrogen Bonded Mixtures