2,7-Disubstituted 1,3,6,8-tetraazabenzopyrenes

Standard

2,7-Disubstituted 1,3,6,8-tetraazabenzopyrenes : Synthesis, characterization, optical and electrochemical properties. / Baranov, Denis S.; Krivenko, Olga L.; Nevostruev, Danil A. et al.

In: Dyes and Pigments, Vol. 168, 01.09.2019, p. 219-227.

Research output: Contribution to journal › Article › peer-review

Author

Baranov, Denis S. ; Krivenko, Olga L. ; Nevostruev, Danil A. et al. / 2,7-Disubstituted 1,3,6,8-tetraazabenzopyrenes : Synthesis, characterization, optical and electrochemical properties. In: Dyes and Pigments. 2019 ; Vol. 168. pp. 219-227.

BibTeX

@article{91c4609559e547468dc6a2a85e60f0e7,

title = "2,7-Disubstituted 1,3,6,8-tetraazabenzopyrenes: Synthesis, characterization, optical and electrochemical properties",

abstract = " 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. ",

keywords = "Alkylation, Double peri-annulation, Nucleophilic substitution, Photophysical properties, Tetraazabenzopyrenes, PERFORMANCE, HETEROACENES, MOLECULAR DESIGN, TRANSISTORS, FLUORESCENCE, NITROGEN, BASIS-SETS, EMISSION, PROBE, ORGANIC PHOTOVOLTAICS",

author = "Baranov, {Denis S.} and Krivenko, {Olga L.} and Nevostruev, {Danil A.} and Glebov, {Evgeni M.} and Uvarov, {Mikhail N.} and Kazantsev, {Maxim S.} and Mostovich, {Evgeny A.} and Kulik, {Leonid V.}",

year = "2019",

month = sep,

day = "1",

doi = "10.1016/j.dyepig.2019.04.062",

language = "English",

volume = "168",

pages = "219--227",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier",

}

RIS

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.

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 -

ID: 20043935