We synthesized new 3,5-bis(hydroxymethyl)phenylacetylene (HPA) monomers connected with a rigid and linear pi-conjugated oligomer. The monomers were successfully polymerized with a rhodium catalyst [Rh(nbd)Cl](2) in the presence of chiral PEA to give the corresponding polymers. Helix-sense-selective polymerization proceeded for DBHPA. CD, UV, and WAXS spectroscopic studies revealed that the intramolecular hydrogen bonds of the polymers contributed to the stabilization of their helical conformation but the stability depended on the length of the rigid and linear pi-conjugated side group.