Novel alkyne chromophore of the isophorone derivatives: synthesis, electrochemical evaluation, DFT, and processable bottom contact/top-gate OFET applications

Abstract

Fused alkyne molecules are important in organic semiconductors due to their desirable properties. Here, we report the design and synthesis of a new series of A-pi-D molecules (III-VII) that can serve as mild electron acceptors to generate wide-bandgap p-type small compounds for use in organic field-effect transistors. The incorporation of donor units into fused isophorone frameworks can be used to tune the frontier molecular orbital energies. The electrochemical, optical, and thermal properties of the compounds were characterized. Compound VI, which has a fused phenyl-substituted alkyne moiety, had the highest occupied molecular orbital energy level as determined by optical and electrochemical analysis. Density functional theory calculations revealed that compounds VI and III had lower hole reorganization energy (lambda h) than the corresponding isophorone extended conjugated-based compounds (I-II). Conversely, compounds I and II had lower electron reorganization energy (lambda e) than the corresponding fused alkyne compounds. This is in line with the observed adiabatic ionization potential and electron affinity values. Consequently, devices fabricated with compound VI exhibited high mobility and low threshold voltage.