Synthesis of isoelectronic polyazomethine and poly(arylene vinylene) by a palladium-catalyzed Suzuki coupling method

Two fully conjugated copolymers containing 2,7-(9,9-dioctyl) fluorene and 3,6-(N-hexyl-9H-carbazole) disubstituted rings and arylene vinylene or azomethine units in the main chain were synthesized through a palladium-catalyzed Suzuki coupling method of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan2-yl)-9,9-dioctyl fluorene with 1,4-bis(6-bromo-N-hexyl-9H-carbazole-3-yl vinyl) benzene or N,N-bis(6-bromo-N-hexyl-9H-carbazole-3-yl methylidene) 1,4-phenylenediamine. Bisbromine arylene vinylene and arylenazomethine monomers were synthesized by condensation of 3-formyl-N-hexyl-6-bromo carbazole with tetraethyl-p-xylylene diphosphonate or 1,4-phenylenediamine. Copolymers were characterized by FTIR, H-1-NMR, DSC, UV-visible and photoluminescence methods. (c) 2005 Society of Chemical Industry.