A novel synthesis of polymers with anthracene and dihydroanthracene subunits in the main chain

A new polycondensation method to connect redox-active and chromophoric subunits by forming a C-C bond and leading to a polyhydrocarbon is described. 1,ω-bis(9,10-Dihydro-9-anthry)alkanes with various alkylene spacers can be deprotonated by butyllithium to afford a monoanion in each dihydroanthracene moiety. Alkylation with dielectrophiles such as dibromoalkanes yields soluble polymers with dihydroanthracene units in the main chain. The reaction proceeds regioselectively in the 9,10-position. Aromatization generates a polymer with anthracene units. The molecular weights are determined by GPC up to Mn = 10 000. To prove the structure and to calibrate the GPC, suitable model compounds were syn…