SYNTHESIS OF A DIPHENYLETHYLENE DERIVATIVE CARRYING AROMATIC TERTIARYAMINE GROUPS AND ITS USE IN CHAIN-END FUNCTIONALIZATION OF ALKYLLITHIUM-INITIATED POLYMERIZATIONS

1,1-Bis[(4-dimethylamino)phenyl]ethylene was successfully synthesized through the 'Wittig type' reaction of 4,4'-bis(dimethylamino)benzophen one with the 'Tebbe' reagent. The methylenation yields were over 80 wt .-% on the basis of the initial amount of benzophenone derivative used . Terminally functionalized polymers having aromatic tertiary amine gr oups at one end or at both ends were prepared by the crossover reactio ns of n-butyllithium (n-BuLi), poly(styryl)lithium (PSLi), and poly(is oprenyl)lithium (PILI) with the diphenylethylene analogue. The functio nalization yields were over 87 mol.-% based on the results of H-1 NMR spectroscopic analysis. The number-average molecular weights of the po lymers based on the ratio [gram of monomer]/[mole of initiator] are in good accordance with those observed from size exclusion chromatograph ic and H-1 NMR spectroscopic analysis (3,0 x 10(3) similar to 7,5 x 10 (3) g/mol).