TY - JOUR
T1 - 2,7-Disubstituted 1,3,6,8-tetraazabenzopyrenes
T2 - Synthesis, characterization, optical and electrochemical properties
AU - Baranov, Denis S.
AU - Krivenko, Olga L.
AU - Nevostruev, Danil A.
AU - Glebov, Evgeni M.
AU - Uvarov, Mikhail N.
AU - Kazantsev, Maxim S.
AU - Mostovich, Evgeny A.
AU - Kulik, Leonid V.
N1 - Publisher Copyright:
© 2019
Copyright:
Copyright 2019 Elsevier B.V., All rights reserved.
PY - 2019/9/1
Y1 - 2019/9/1
N2 - The syntheses of 2,7-diamino-1,3,6,8-tetraazabenzopyrene framework was achieved through CuI-catalyzed double annulation of 1,4-diiodoanthraquinone with guanidine. In addition, the preparation of series of 2,7-disubstituted 1,3,6,8-tetraazabenzopyrenes functionalized by NR 2 , C[dbnd]O, Cl, alkoxy and phenoxy groups with good yields was achieved through the simple transformations such as diazotization, alkylation and nucleophilic aromatic substitution. The properties of 1,3,6,8-tetraazabenzopyrenes synthesized were studied by DFT-calculations, optical and photoluminescence spectroscopy, cyclic voltammetry and light-induced EPR spectroscopy. The luminescence of amino derivatives is quenched in acidic solutions depending on the degree of protonation.
AB - The syntheses of 2,7-diamino-1,3,6,8-tetraazabenzopyrene framework was achieved through CuI-catalyzed double annulation of 1,4-diiodoanthraquinone with guanidine. In addition, the preparation of series of 2,7-disubstituted 1,3,6,8-tetraazabenzopyrenes functionalized by NR 2 , C[dbnd]O, Cl, alkoxy and phenoxy groups with good yields was achieved through the simple transformations such as diazotization, alkylation and nucleophilic aromatic substitution. The properties of 1,3,6,8-tetraazabenzopyrenes synthesized were studied by DFT-calculations, optical and photoluminescence spectroscopy, cyclic voltammetry and light-induced EPR spectroscopy. The luminescence of amino derivatives is quenched in acidic solutions depending on the degree of protonation.
KW - Alkylation
KW - Double peri-annulation
KW - Nucleophilic substitution
KW - Photophysical properties
KW - Tetraazabenzopyrenes
KW - PERFORMANCE
KW - HETEROACENES
KW - MOLECULAR DESIGN
KW - TRANSISTORS
KW - FLUORESCENCE
KW - NITROGEN
KW - BASIS-SETS
KW - EMISSION
KW - PROBE
KW - ORGANIC PHOTOVOLTAICS
UR - http://www.scopus.com/inward/record.url?scp=85065059896&partnerID=8YFLogxK
U2 - 10.1016/j.dyepig.2019.04.062
DO - 10.1016/j.dyepig.2019.04.062
M3 - Article
AN - SCOPUS:85065059896
VL - 168
SP - 219
EP - 227
JO - Dyes and Pigments
JF - Dyes and Pigments
SN - 0143-7208
ER -