SYNTHESIS OF CONJUGATED MICROPOROUS POLYMER FROM NEW THIOPHENE DERIVATIVES

Abstract

Four brominated thiophene derivatives: (5,7-dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methanol (compound 29), (5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methyl 4-methylbenzenesulfonate (compound 30), (5,7-dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methyl 2-chloroacetate (compound 32) and (±)-1,3-Dibromo-4a,5,6,7,8,8a-hexahydrobenzo[e]thieno[3,4-b][1,4]dioxine (compound 37) were a group of monomers that could undergo solid state polymerization. The reactions of compound 29 and 30 were more facile than DBEDOT, although the SSP of compound 37 required higher temperature. Polymers of compound 29, 30 and 37 show higher conductivity than PEDOT. Three derivatives of linked multithiophenes: Bis((2,3-dihydrothieno[3,4-b]dioxin-2-yl)methyl) [1',4']benzene dicarboxylate, Bis((2,3-dihydrothieno[3,4-b][1,4]dioxin-2yl)methyl)malonate and Tris((2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methyl) benzene-1,3,5-tricarboxylate were prepared. They could be turned into the corresponding polymers by chemical polymerizations. The conductivity data indicated that they were relatively poor conductors. However, incorporating 5% of Poly (bis((2,3-dihydrothieno[3,4-b]dioxin-2-yl)methyl) [1',4']benzene dicarboxylate) into PEDOT did not alter electrical conductivity and morphology of PEDOT, but significantly increased the surface area and turned the polymer mixture into a porous conductive material.