Synthesis of macrocyclic polystyrene and macrocyclic poly(9,9-dimethyl-2-vinylfluorene) containing a single 9,10-anthracenylidene group

Polystyryldilithium (PSLi2), polystyryldipotassium (PSK2) or poly(9,9-dimet hyl-2-vinylfluorene)yl dipotassium (PDMVF-K-2), generated by electron trans fer initiated polymerizations, were reacted with 9,10-bis(chloromethyl)anth racene (BCMA) under high dilution conditions to afford 9,10-anthracenyliden e labeled PS or PDMVF macrocycles. However, only potassium ion mediated cou pling reactions with BCMA. gave high extents of 9,10-anthracenylidene incor poration (>90%) while analogous lithium ion systems afforded no more than 5 0% incorporation. Coupling reactions of PSK2 with 9,10-bis(bromomethyl)anth racene (BBMA) also gave lower degrees of coupling and 9,10-anthracenylidene incorporation. Metal-halogen exchange or electron-transfer reactions may b e responsible for the lower degree of 9,10-anthracenylidene labeling.