Design and synthesis of new Pentacene derivatives containing Dimethoxydiphenylamine arms and theoretical study

• A novel series of arylamine-capped pentacene derivatives have been reported for the first time. • The length of the aryl spacer and the nature of the arms were modified to study their effects on the structure-property relationship. • These unprecedented compounds showed excellent solubility and stability, high thermal stability and high rigidity. • Strong candidates for organic thin-film transistors and interface layers in perovskite solar cells. In a quest of exploitation of soluble and stable pentacene derivatives for organic electronics devices or for interface layers in perovskite solar cells, a novel series of arylamine-capped pentacene derivatives namely DMPA(Ph)Pent, DMPA(Ph) 2 Pent, DMPA(Ph) 3 Pent , and Cz(Ph)Pent were synthesized, characterized, and studied. Two key parameters were investigated in this work: i) the length of the aryl spacer and ii) the substitution of dimethoxyphenylamine (DMPA) arms with carbazole-DMPA arms, to study their effects on the structure-property relationship. These unprecedented compounds, synthesized via a two-step, showed excellent solubility and stability as a result of the introduction of DMPA and carbazole-DMPA arms. The HOMO-LUMO energy gaps were calculated through experimentally and theoretically. These new pentacene derivatives exhibited high thermal stability, with decomposition temperatures around 470 °C and high rigidity with glass transition temperatures ranging from 125 °C to 231 °C. These promising thermal and electrochemical properties highlight these new soluble and stable materials as potential strong candidates for a range of applications, including organic thin-film transistors and interface layers in perovskite solar cells.