The synthesis of a novel silylcarborane-containing fluorene monomer is reported in the present paper. Homo- and copolymerization via microwave-assisted Ni(0)-medialed coupling are described, and the influence of sterically crowded silylcarboranes on the polymerization outcome is assessed. The fluorescence spectra and thermal characteristics of the resulting polymers are analyzed and compared to determine the impact of carborane cages. Pendant carboranes are shown to improve the stability of annealed thin films. and potential implications in sensing devices and neutron detection are discussed.