The double-twisted helical structure was confirmed for the first time for t
he smectic phase of a banana-shaped molecular system from observation of th
e microscopic pattern. Optically polarized microscopic textures and phase t
ransitions of 1,3-phenylene bis [4-(3-chloro-3-n-octyloxyphenyliminomethyl)
benzoate (PBCOB) and related compounds are described. The chloro-substitue
nt introduced into the 3-position of the Schiff's base moiety of the banana
-shaped molecule destabilized the smectic phase and enhanced new mesomorphi
c properties. The mesophases exhibited by the octyloxy homologue of the chl
oro-substituted compound were of the smectic phases, SmX1 and SmX2. The mix
ing behaviour between chloro-substituted and non-chloro-substituted compoun
ds resulted in the appearance of a wide miscibility gap and enlargement of
the SmX1 phase which can be seen in a lateral chloro-substituted compound.