TY - JOUR

T1 - Diaza-analogs of benzopyrene and perylene containing thienyl and 4-(phenylamino)phenyl groups

T2 - Synthesis, characterization, optical and electrochemical properties

AU - Baranov, Denis S.

AU - Uvarov, Mikhail N.

AU - Kazantsev, Maxim S.

AU - Mostovich, Evgeny A.

AU - Glebov, Evgeni M.

AU - Gatilov, Yurii V.

AU - Kulik, Leonid V.

N1 - Publisher Copyright: © 2016 Elsevier Ltd

PY - 2017/1/1

Y1 - 2017/1/1

N2 - 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 π-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.

AB - 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 π-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.

KW - Diazabenzopyrenes

KW - Diazaperylenes

KW - Push-pull polycondensed small molecules

KW - Solid-state luminescence

KW - SOLAR-CELLS

KW - PYRENE

KW - SEMICONDUCTORS

KW - COMPOSITES

KW - TRANSISTORS

KW - FLUORESCENCE

KW - DIIMIDES

KW - NAPHTHALENE

KW - BASIS-SETS

KW - INDUCED ELECTRON-TRANSFER

UR - http://www.scopus.com/inward/record.url?scp=84988481796&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2016.09.026

DO - 10.1016/j.dyepig.2016.09.026

M3 - Article

AN - SCOPUS:84988481796

VL - 136

SP - 707

EP - 714

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

ER -