Side-chain supramolecular polymers that show columnar mesomorphism have been prepared through H-bonding interactions between a polyvinylpyridine polymer as H-acceptor and different H-donors derived from benzoic acid. These compounds have been designed according to a promesogenic structure, that is, either disk-like or banana-like, to promote stacking and therefore the formation of columnar arrangements. IR studies confirmed the formation of H-bonds and demonstrated that the H-bond intensity decreases upon increasing temperature. The mesophase organizations were studied by polarized optical microscopy, differential scanning calorimetry, and X-ray diffraction. Associations containing poly-3-methyl-4-vinylpyridine showed supramolecular optical activity, as evidenced by circular dichroism studies oil thin films. It is proposed that these supramolecular polymers adopt a helical structure that can be biased toward a given handedness by virtue of the configuration of the stereogenic centers in the peripheral tails of the acids. (C) 2008 Wiley Periodicals, Inc.