Synthesis, Thermal, Optical and Electrochemical Properties of Acridone and Thioxanthone Based Push-Pull Molecules

Abstract

© 2020 Wiley-VCH GmbH Two series of eight visible-light-absorbing redox active molecules derived from 9(10H)-acridone and thioxanthen-9-one were designed and synthetized. The different dyes were characterized by UV-vis absorption and fluorescent spectroscopy, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and cyclic voltammetry (CV) for their thermal, optical and electrochemical properties, respectively. Theoretical calculations DFT were also carried out to support the experimental results. These molecules are thermally stable with Td (decomposition temperature) range from 290 °C to 418 °C and have glass forming properties with Tg (glass transition temperature) varying from 44 °C to 134 °C. These chromophores strongly absorb and emit in the visible spectral range (400–550 nm for absorption and 450–650 for fluorescence). Their frontier orbitals’ energy levels as well as optical bandgaps can be tuned by changing the nature and the number of the arylamine electron-donating groups. These compounds have been found to be promising candidates for photo-initiators for photo-polymerization process applied in 3D printing technique. They could also be potentially applied as hole transporting materials for hybrid perovskite photovoltaics.