A cholesteryloxyallene (1) bearing chiral cholesteryl pendant group was designed and synthesized. Living polymerization of this monomer with an allylnickel complex as a catalyst give poly(cholesteryloxyallene)s (poly-1(m)s) in high yields with controllable molecular weights and narrow molecular weight distributions. These polymers were found to possess a dynamic helical conformation with a preferred handedness in n-hexane as confirmed by circular dichroism and absorption spectra as well as optical ratios. The helical conformation of the polymers was revealed to stabilize as the number of repeat units increased until the degree of polymerization reached 100. The helical conformation of poly-1(100) could be controlled by altering the temperature of solutions. (c) 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2227-2233