Home / Publications / Assembly of annulated 1,3-diazapyrenes by consecutive cross-coupling and cyclodehydrogenation of (het)arene moieties

Assembly of annulated 1,3-diazapyrenes by consecutive cross-coupling and cyclodehydrogenation of (het)arene moieties

Egor Vladimirovich Verbitskiy 1, 2
Egor Vladimirovich Verbitskiy
, 
Ekaterina Mikhailovna Dinastiya 1
Ekaterina Mikhailovna Dinastiya
, 
Oleg Stanislavovich Eltsov 1, 2
Oleg Stanislavovich Eltsov
, 
Ekaterina Fedorovna Zhilina 1
Ekaterina Fedorovna Zhilina
, 
Alexander V Shchepochkin 1, 2
Alexander V Shchepochkin
, 
Gennady Leonidovich Rusinov 1, 2
Gennady Leonidovich Rusinov
, 
Oleg Nikolaevich Chupakhin 1, 2
Oleg Nikolaevich Chupakhin
, 
Valery Nikolaevich Charushin 1, 2
Valery Nikolaevich Charushin
10.1016/j.mencom.2020.03.003
Published 2020-03-02
Communication , Volume 30, Issue 2, 142-144
13
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Verbitskiy E. V. et al. Assembly of annulated 1,3-diazapyrenes by consecutive cross-coupling and cyclodehydrogenation of (het)arene moieties // Mendeleev Communications. 2020. Vol. 30. No. 2. pp. 142-144.
GOST all authors (up to 50) Copy
Verbitskiy E. V., Dinastiya E. M., Eltsov O. S., Zhilina E. F., Shchepochkin A. V., Rusinov G. L., Chupakhin O. N., Charushin V. N. Assembly of annulated 1,3-diazapyrenes by consecutive cross-coupling and cyclodehydrogenation of (het)arene moieties // Mendeleev Communications. 2020. Vol. 30. No. 2. pp. 142-144.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2020.03.003
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.003
TI - Assembly of annulated 1,3-diazapyrenes by consecutive cross-coupling and cyclodehydrogenation of (het)arene moieties
T2 - Mendeleev Communications
AU - Verbitskiy, Egor Vladimirovich
AU - Dinastiya, Ekaterina Mikhailovna
AU - Eltsov, Oleg Stanislavovich
AU - Zhilina, Ekaterina Fedorovna
AU - Shchepochkin, Alexander V
AU - Rusinov, Gennady Leonidovich
AU - Chupakhin, Oleg Nikolaevich
AU - Charushin, Valery Nikolaevich
PY - 2020
DA - 2020/03/02
PB - Mendeleev Communications
SP - 142-144
IS - 2
VL - 30
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2020_Verbitskiy,
author = {Egor Vladimirovich Verbitskiy and Ekaterina Mikhailovna Dinastiya and Oleg Stanislavovich Eltsov and Ekaterina Fedorovna Zhilina and Alexander V Shchepochkin and Gennady Leonidovich Rusinov and Oleg Nikolaevich Chupakhin and Valery Nikolaevich Charushin},
title = {Assembly of annulated 1,3-diazapyrenes by consecutive cross-coupling and cyclodehydrogenation of (het)arene moieties},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.003},
number = {2},
pages = {142--144},
doi = {10.1016/j.mencom.2020.03.003}
}
MLA
Cite this
MLA Copy
Verbitskiy, Egor Vladimirovich, et al. “Assembly of annulated 1,3-diazapyrenes by consecutive cross-coupling and cyclodehydrogenation of (het)arene moieties.” Mendeleev Communications, vol. 30, no. 2, Mar. 2020, pp. 142-144. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.003.

Abstract

Di(het)areno[e,l][1,3]diazapyrene core was constructed by FeCl3-mediated intramolecular oxidative cyclodehydrogenation of 5-[2,6-di(het)arylphenyl]pyrimidine precursors, which in turn were obtained by the Suzuki cross-coupling of 5-(2,6-dibromophenyl)pyrimidine derivative with the corresponding (het)arylboronic acids. Molecular orbital calculations as well as redox and photophysical measurements show that the fused products are promising for organic electronic application.

References

1.
Pyrene-Based Materials for Organic Electronics
Figueira-Duarte T.M., Müllen K.
Chemical Reviews, 2011
2.
1,3,6,8-Tetraazapyrenes: Synthesis, Solid-State Structures, and Properties as Redox-Active Materials
Geib S., Martens S.C., Zschieschang U., Lombeck F., Wadepohl H., Klauk H., Gade L.H.
Journal of Organic Chemistry, 2012
5.
Heteroatom-Doped Nanographenes with Structural Precision
Wang X., Yao X., Narita A., Müllen K.
Accounts of Chemical Research, 2019
6.
Pyrimidines as Surrogates for 1,3-Dicarbonyl Compounds inperiAnnulation of Perimidines en Route to 1,3-Diazapyrenes
Aksenov A.V., Shcherbakov S.V., Lobach I.V., Aksenova I.V., Rubin M.
European Journal of Organic Chemistry, 2017
7.
Heteroacenes Bearing the Pyrimidine Scaffold: Synthesis, Photophysical and Electrochemical Properties
Verbitskiy E.V., Cheprakova E.M., Makarova N.I., Dorogan I.V., Metelitsa A.V., Minkin V.I., Slepukhin P.A., Svalova T.S., Ivanova A.V., Kozitsina A.N., Rusinov G.L., Chupakhin O.N., Charushin V.N.
European Journal of Organic Chemistry, 2016
8.
10.1016/j.mencom.2020.03.003_bib0040
Grzybowski
Angew. Chem., Int. Ed., 2019
10.
Recent Advances in Direct C–H Functionalization of Pyrimidines
Verbitskiy E., Rusinov G., Chupakhin O., Charushin V.
Synthesis, 2017
11.
New approach to unsymmetrical 1,3-diazatriphenylenes through intramolecular oxidative cyclodehydrogenation
Verbitskiy E.V., Eltsov O.S., Zhilina E.F., Pakhomov I.M., Rusinov G.L., Chupakhin O.N., Charushin V.N.
Tetrahedron, 2019
12.
K. Rurack, in Standardization and Quality Assurance in Fluorescence Measurements I. Techniques (Springer Series on Fluorescence, ed. M. Hof, vol. 5), ed. U. Resch-Genger, Springer, Berlin, 2008, pp. 101-145.
13.
10.1016/j.mencom.2020.03.003_bib0065
Ghalib
Aust. J. Basic Appl. Sci., 2014
14.
Thienoacene-Based Organic Semiconductors
Takimiya K., Shinamura S., Osaka I., Miyazaki E.
Advanced Materials, 2011