Polystyryldilithium (PSLi2), polystyryldipotassium (PSK2) or poly(9,9-dimethyl-2-vinylfluorene)yl dipotassium (PDMVF-K-2), generated by electron transfer initiated polymerizations, were reacted with 9,10-bis(chloromethyl)anthracene (BCMA) under high dilution conditions to afford 9,10-anthracenylidene labeled PS or PDMVF macrocycles. However, only potassium ion mediated coupling reactions with BCMA. gave high extents of 9,10-anthracenylidene incorporation (>90%) while analogous lithium ion systems afforded no more than 50% incorporation. Coupling reactions of PSK2 with 9,10-bis(bromomethyl)anthracene (BBMA) also gave lower degrees of coupling and 9,10-anthracenylidene incorporation. Metal-halogen exchange or electron-transfer reactions may be responsible for the lower degree of 9,10-anthracenylidene labeling.