Phenyl groups were successively introduced at the bridgehead positions of cage compound HC(SiMe2SiMe2)(3)CH via deprotonation-cyclohexenylation-dehydrogenation. UV absorption spectra of the cage compounds suggested the possibility of electronic interaction between the cage and aromatic moieties. Bromination of the phenylated cage molecule gave a p-bromo derivative that was transformed to liquid crystalline compounds.