Diaza-analogs of benzopyrene and perylene containing thienyl and 4-(phenylamino)phenyl groups: Synthesis, characterization, optical and electrochemical properties

作者：Baranov Denis S; Uvarov Mikhail N; Kazantsev Maxim S; Mostovich Evgeny A; Glebov Evgeni M; Gatilov Yurii V; Kulik Leonid V

来源：Dyes and Pigments, 2017, 136: 707-714.

DOI：10.1016/j.dyepig.2016.09.026

• Diazabenzopyrenes
• Diazaperylenes
• Push-pull polycondensed small molecules
• Solid-state luminescence

Series of 1,8-diazabenzopyrenes and 1,7-diazaperylenes with thienyl or 4-(phenylamino)phenyl groups were designed and synthesized by a one-pot process from the functionalized terminal alkynes and either 1,4- or 1,5-diiodoanthraquinones in order to investigate the effect of extending pi-conjugation at the 2,7 and 2,8-positions on the optical and electrochemical properties. The substances synthesized were characterized by X-ray analysis, cyclic voltammetry, UV-vis and luminescence spectroscopy. Energies and spin-densities of frontier molecular orbitals were calculated by DFT. Practically planar crystal structures of 1,8-diazabenzopyrene and 1,7-diazaperylene with thienyl groups were confirmed by X-ray diffraction data. Solid-state luminescence was obtained for the synthesized substances in drop-casted films and in 1,4-dioxane/water mixtures.

• 出版日期2017-1