Home / Publications / 2-Thienyl-substituted 3a,6a-diaza-1,4-diphosphapentalene: Synthesis and complexation with 1,2,4,5-tetracyanobenzene

2-Thienyl-substituted 3a,6a-diaza-1,4-diphosphapentalene: Synthesis and complexation with 1,2,4,5-tetracyanobenzene

Matvey Daniilovich Grishin 1
Matvey Daniilovich Grishin
, 
Nataliya Vadimovna Zolotareva 1
Nataliya Vadimovna Zolotareva
, 
Yuliya Sergeevna Panova 1
Yuliya Sergeevna Panova
, 
Vyacheslav Victorovich Suschev 1
Vyacheslav Victorovich Suschev
, 
Roman Valeryevich Rumyantcev 1
Roman Valeryevich Rumyantcev
, 
Georgy Konstantinovich Fukin 1
Georgy Konstantinovich Fukin
, 
Alexander Nikolaevich Kornev 1
Alexander Nikolaevich Kornev
1 G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, Nizhnii Novgorod, Russian Federation
10.1016/j.mencom.2023.09.013
Published 2023-09-01
Communication , Volume 33, Issue 5, 631-634
4
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Grishin M. D. et al. 2-Thienyl-substituted 3a,6a-diaza-1,4-diphosphapentalene: Synthesis and complexation with 1,2,4,5-tetracyanobenzene // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 631-634.
GOST all authors (up to 50) Copy
Grishin M. D., Zolotareva N. V., Panova Y. S., Suschev V. V., Rumyantcev R. V., Fukin G. K., Kornev A. N. 2-Thienyl-substituted 3a,6a-diaza-1,4-diphosphapentalene: Synthesis and complexation with 1,2,4,5-tetracyanobenzene // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 631-634.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2023.09.013
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.013
TI - 2-Thienyl-substituted 3a,6a-diaza-1,4-diphosphapentalene: Synthesis and complexation with 1,2,4,5-tetracyanobenzene
T2 - Mendeleev Communications
AU - Grishin, Matvey Daniilovich
AU - Zolotareva, Nataliya Vadimovna
AU - Panova, Yuliya Sergeevna
AU - Suschev, Vyacheslav Victorovich
AU - Rumyantcev, Roman Valeryevich
AU - Fukin, Georgy Konstantinovich
AU - Kornev, Alexander Nikolaevich
PY - 2023
DA - 2023/09/01
PB - Mendeleev Communications
SP - 631-634
IS - 5
VL - 33
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2023_Grishin,
author = {Matvey Daniilovich Grishin and Nataliya Vadimovna Zolotareva and Yuliya Sergeevna Panova and Vyacheslav Victorovich Suschev and Roman Valeryevich Rumyantcev and Georgy Konstantinovich Fukin and Alexander Nikolaevich Kornev},
title = {2-Thienyl-substituted 3a,6a-diaza-1,4-diphosphapentalene: Synthesis and complexation with 1,2,4,5-tetracyanobenzene},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.013},
number = {5},
pages = {631--634},
doi = {10.1016/j.mencom.2023.09.013}
}
MLA
Cite this
MLA Copy
Grishin, Matvey Daniilovich, et al. “2-Thienyl-substituted 3a,6a-diaza-1,4-diphosphapentalene: Synthesis and complexation with 1,2,4,5-tetracyanobenzene.” Mendeleev Communications, vol. 33, no. 5, Sep. 2023, pp. 631-634. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.013.

Keywords

1
2
4
5-tetracyanobenzene
charge-transfer complexes
cyclic voltammetry.
diazadiphosphapentalenes
electronic spectroscopy
phosphinidenes
X-ray diffraction

Abstract

Synthesis of 2,5-dimethyl-3,6-di(2-thienyl)-3a,6a-diaza-1,4-diphosphapentalene was accomplished. Interaction of this compound with 1,2,4,5-tetracyanobenzene afforded black crystals of the 1 : 1 adduct containing π-stacks of D-A units with short interplanar spacing of 3.26 A inside the unit and 3.47 A between the D-A units, where tetracyanobenzene is an acceptor of 0.2 e. Estimation of the HOMO−LUMO gap from the onset of optical absorption gave value of 1.28 eV.

References

.
Chulanova E.A., Semenov N.A., Pushkarevsky N.A., Gritsan N.P., Zibarev A.V.
Mendeleev Communications, 2018
.
Charge-transfer complexes: new perspectives on an old class of compounds
Goetz K.P., Vermeulen D., Payne M.E., Kloc C., McNeil L.E., Jurchescu O.D.
Journal of Materials Chemistry C, 2014
.
Organic Donor–Acceptor Complexes as Novel Organic Semiconductors
Zhang J., Xu W., Sheng P., Zhao G., Zhu D.
Accounts of Chemical Research, 2017
.
Recent Advances in the Chemistry of Anellated Azaphospholes
Bansal R., Gupta N., Kumawat S.
Current Organic Chemistry, 2006
.
Maleeva A.V., Ershova I.V., Trofimova O.Y., Arsenyeva K.V., Yakushev I.A., Piskunov A.V.
Mendeleev Communications, 2022
.
Crystal Growth, Structure, and Transport Properties of the Charge-Transfer Salt Picene/2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane
Mahns B., Kataeva O., Islamov D., Hampel S., Steckel F., Hess C., Knupfer M., Büchner B., Himcinschi C., Hahn T., Renger R., Kortus J.
Crystal Growth and Design, 2014
.
The Nature of P(σ2λ3↔σ2λ1) Dualism: 3a,6a-Diaza-1,4-diphosphapentalene as a Form of Stabilized Singlet Phosphinidene
Kornev A.N., Panova Y.S., Sushev V.V., Dorado Daza D.F., Novikov A.S., Cherkasov A.V., Fukin G.K., Abakumov G.A.
Inorganic Chemistry, 2019
.
Dual Reactivity of 3a,6a-Diaza-1,4-diphosphapentalene: π-Donor versus n-Donor
Panova Y.S., Sushev V.V., Dorado Daza D.F., Zolotareva N.V., Rumyantcev R.V., Fukin G.K., Kornev A.N.
Inorganic Chemistry, 2020
.
1,1‐ and 1,4‐Addition Reactions with 3a,6a‐Diaza‐1,4‐diphosphapentalene Containing Two‐Coordinate and Formally Divalent Phosphorus
Kornev A.N., Galperin V.E., Sushev V.V., Zolotareva N.V., Baranov E.V., Fukin G.K., Abakumov G.A.
European Journal of Inorganic Chemistry, 2016
.
Reactions of 3а,6a-diaza-1,4-diphosphapentalene with activated acetylenes
Kornev A.N., Galperin V.E., Panova Y.S., Sushev V.V., Cherkasov A.V., Arapova A.V., Abakumov G.A.
Russian Chemical Bulletin, 2018
.
Tetrathiafulvalene derivatives for organic field effect transistors
Mas-Torrent M., Rovira C.
Journal of Materials Chemistry A, 2006
.
Rearrangements and reductive cleavage of 3a,6a-diaza-1,4-diphosphapentalenes
Panova Y.S., Khristolyubova A.V., Sushev V.V., Zolotareva N.V., Baranov E.V., Fukin G.K., Kornev A.N.
New Journal of Chemistry, 2021
.
Interaction of dicoordinate phosphorus with boranes: chemistry of 3a,6a-diaza-1,4-diphosphapentalene as masked phosphinidene
Panova Y., Khristolyubova A., Zolotareva N., Sushev V., Galperin V., Rumyantcev R., Fukin G., Kornev A.
Dalton Transactions, 2021
.
The Structure of Fractionally Charged Tetracyanobenzenen− Present in [TCNB]32−
Bagnato J.D., Shum W.W., Strohmeier M., Grant D.M., Arif A.M., Miller J.S.
Angewandte Chemie - International Edition, 2006
.
3a,6a‐Diaza‐1,4‐diphosphapentalenes: Synthesis and Complexation with the Organic π‐Acceptor 1,2,4,5‐Tetracyanobenzene
Zolotareva N., Sushev V., Panova Y., Khristolyubova A., Grishin M., Rumyantcev R., Fukin G., Kornev A.N.
ChemPlusChem, 2023