Functionalized arylacetylene oligomers for Organic Thin-Film Transistors (OTFTs)

Abstract

The preparation of arylacetylene oligomers comprising of three repeating phenylene ethynylene units containing para-substituted electron-donating or electron-withdrawing substitutents was analyzed. The compounds were prepared with product yields up to 91% using a synthetic strategy based on a simple iterative and convergent Pd/Cu-coupling and desilylation protocol. The preparation included treatment of the respective trialkylsilyl iodide and terminal arylalkyne starting material in the presence of PdCl 2(PPh3)2 and CuI at room temperature. It was observed that the relative planar configuration of arylacetylene moieties along the molecules was important for the on-off switch stage.