Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes

• DOI: 10.1002/cptc.202100127
• Publication Date: 2021-09-14T09:16:32Z
• Authors: Jan Richtar; Martin Ciganek; Anna Jancik Proch...; Alexander Kovalenko; Hathaichanok Seel...; Matouš Kratochvíl; Martin Weiter; Cigdem Yumusak; Niyazi Serdar Sar...; Vladimir Lukeš; Jozef Krajcovic
• Keywords: Adamantane; Thermal Stability; HOMO/LUMO

Abstract The synthesis, experimental and theoretical study of the novel air‐stable four adamantane‐bearing dyes based on trans‐ epindolidione ( EPI ) quinacridone QA cores are presented. Compared to parent , methyl‐/ethyladamantyl substitution ensures that their structural stability in crystals is preserved due self‐organizing properties adamantyl groups. investigated materials solution‐processable common organic solvents possess excellent thermal stability. very good solubility was achieved by a one‐step short easy which resulted moderate yields new family synthesized dyes. ethyladamantyl derivative 3 exhibits unique rise reaching 412 °C. resulting electrochemical band gap carried out thin‐film evaporated ITO‐coated glass electrodes range 2.4–2.5 eV. HOMO energies from −6.2 −6.0 eV, LUMO lay between −3.7 −3.5 prepared compounds characterized strong fluorescence solutions powder, suggesting decrease extent non‐radiative relaxation processes.