The direct and nearly quantitative incorporation of 9,10-anthracenylidene (AN) chromophores into polystyrene occurred via the reaction of polystyryllithimn (PSLi) with 9,10-bis(chloromethyl)anthracene (BCMA) at -78 degreesC in tetrahydrofuran (THF)/ hexane containing between 30 and 40 vol % hexane. Although the reaction of PSLi and BCMA or 9,10-bis(bromomethyl)anthracene (BBMA) in THF at -78 degreesC gave nearly quantitative coupling, typically only 30-50% AN incorporation was observed, as determined by ultraviolet-visible spectrometry. Model coupling reactions of 3,3-dimethyl-1,1-diphenyl-1-lithiobutane, (1,1,2,2-tetramethyl)propylcyclopentadienyllithium, 9-methylfluorenyllithium, and triphenylmethyllithium with BCMA or BBMA at -78 degreesC in THF in nearly all cases gave several AN-containing coupling products. This was consistent with lithium-halogen exchange leading to the linking of multiple AN groups.