A cruciform 6, 6′-dipentacenyl: Synthesis, solid-state packing and applications in thin-film transistors

Abstract

A novel molecular design concept 6,6'-linked pentacene dimer, 13,13'-bis(triisopropylsilylethynyl)-6,6'-dipentacenyl (Dips-TIPS) for high-performance organic semiconductors by using cruciform molecules as potential 2D isotropic charge transporting materials was reported. Dip-TIPS, exhibits the desired two-directional isotropic face-to-face π stacking, and FET mobilities of up to 0.11 cm2V-1s-1 were obtained based on vapor-deposited thin films. Dip-TIPS have good solubility in normal organic solvents, such as chloroform and THF. The absorption spectrum of Dip-TIPS in thin film displays an obvious bathochromic shift, which suggests that the molecules adopt a π-aggregated form in the solid state. The electrochemical properties of Dip-TIPS were investigated in CH 2Cl2, by using cyclic voltammetry. Differential scanning calorimetry (DSC) measurement of Dip-TIPS did not show any transitions below 350°C.