Ladder-type conjugated oligomers prepared by the Scholl oxidative cyclodehydrogenation reaction: synthesis, characterization and application in field effect transistors

Abstract

Two novel well defined ladder-type conjugated oligomers have been successfully designed and synthesized through a solution processing method in an excellent yield. The field effect transistors (FETs) fabricated by these ladder-type oligomers with a nice planar structure exhibit excellent charge carrier mobilities, up to 0.10 cm² V⁻¹ s⁻¹ and 0.33 cm² V⁻¹ s⁻¹; furthermore, the devices can work well with a low gate voltage. The ladder-type oligomers are both converted from two precursor co-oligomers, poly(2,7-(1,2,-diphenylethene)-9,9-dioctylfluorene) (PDPF), via an anhydrous FeCl₃ oxidative cyclodehydrogenation. The pronounced red shift shown in the preliminary photoluminescence spectra and the changes of band gaps measured by electrochemical analysis both testify that the better electronic transmission capacity in the FET performance is due to the expanded molecular chain planarization after the chemical cyclodehydrogenation. Interestingly, the precursor oligomers having a linear-type chain and a zigzag-type chain (L-PDPF and Z-PDPF, respectively) show many characteristic differences in their thermal, optical and electrochemical properties. The differences caused by the different types of main chains demonstrate that the macromolecular configurations have a tremendous impact on the functioning of the oligomers.