A series of new norbornene carboxylic cholesteryl ester monomers with and without alkyl spacers, NBCh, and NBCh-n, respectively, were synthesized. New side-chain liquid crystalline homopolymers, PNBCh and PNBCh-n, were cleanly prepared using NBCh and NBCh-n, respectively, with Grubbs 2nd generation catalyst. Molecular and structural characterization of monomers and polymers were carried out by nuclear magnetic resonance, NMR, Fourier transform infrared, FT-IR, spectroscopy, and gel permeation chromatography, GPC. The thermal and liquid crystalline properties of the homopolymers were investigated by differential scanning calorimetry, DSC, thermogravimetric analysis, TGA, and polarized optical microscopy, POM. Small angle and wide angle X-ray studies of PNBCh-n in powder and fiber states not only confirmed the formation of smectic A mesophases, but also established their morphologies. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polyrn Chem 47: 2690-2701, 2009