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9-[6-(Diphenylphosphino)pyridin-2-yl]-9H-carbazole: synthesis and coordination properties toward CuI and PdII

Andrey Yu Baranov 1
Andrey Yu Baranov
, 
Irina Yuryevna Bagryanskaya 2
Irina Yuryevna Bagryanskaya
, 
Alexandr Viktorovich Artem’ev 1
Alexandr Viktorovich Artem’ev
1 A. V. Nikolaev Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russian Federation
2 N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russian Federation
10.71267/mencom.7548
Published 2025-01-24
Communication , Volume 35, Issue 1, 39-41
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Baranov A. Yu., Bagryanskaya I. Y., Artem’ev A. V. 9-[6-(Diphenylphosphino)pyridin-2-yl]-9H-carbazole: synthesis and coordination properties toward CuI and PdII // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 39-41.
GOST all authors (up to 50) Copy
Baranov A. Yu., Bagryanskaya I. Y., Artem’ev A. V. 9-[6-(Diphenylphosphino)pyridin-2-yl]-9H-carbazole: synthesis and coordination properties toward CuI and PdII // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 39-41.
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TY - JOUR
DO - 10.71267/mencom.7548
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7548
TI - 9-[6-(Diphenylphosphino)pyridin-2-yl]-9H-carbazole: synthesis and coordination properties toward CuI and PdII
T2 - Mendeleev Communications
AU - Baranov, Andrey Yu
AU - Bagryanskaya, Irina Yuryevna
AU - Artem’ev, Alexandr Viktorovich
PY - 2025
DA - 2025/01/24
PB - Mendeleev Communications
SP - 39-41
IS - 1
VL - 35
ER -
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@article{2025_Baranov,
author = {Andrey Yu Baranov and Irina Yuryevna Bagryanskaya and Alexandr Viktorovich Artem’ev},
title = {9-[6-(Diphenylphosphino)pyridin-2-yl]-9H-carbazole: synthesis and coordination properties toward CuI and PdII},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7548},
number = {1},
pages = {39--41},
doi = {10.71267/mencom.7548}
}
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Baranov, Andrey Yu., et al. “9-[6-(Diphenylphosphino)pyridin-2-yl]-9H-carbazole: synthesis and coordination properties toward CuI and PdII.” Mendeleev Communications, vol. 35, no. 1, Jan. 2025, pp. 39-41. https://mendcomm.colab.ws/publications/10.71267/mencom.7548.

Keywords

9-[6-(diphenylphosphino)pyridin-2-yl]-9H-carbazole
copper(I) iodide complexes
crystal structure
palladium(II) chloride complexes
phosphonium salt

Abstract

9-[6-(Diphenylphosphino)pyridin-2-yl]-9H-carbazole was synthesized in two steps involving cross-coupling of 2,6-dibromopyridine with carbazole followed by treatment of the formed monobromo pyridine derivative with Ph2PCl. The coordination properties of the synthesized ligand were demonstrated by the reaction with Pd(COD)Cl2 and CuI. The alkylation of the title compound with MeI proceeds selectively at the P atom to afford the corresponding phosphonium salt.

Funders

Ministry of Education and Science of the Russian Federation

References

1.
SHELXT– Integrated space-group and crystal-structure determination
Sheldrick G.M.
Acta Crystallographica Section A: Foundations and Advances, 2015
2.
van der Waals Volumes and Radii
Bondi A.
The Journal of Physical Chemistry, 1964
3.
Phosphine-pyridyl and related ligands in synthesis and catalysis
Espinet P., Soulantica K.
Coordination Chemistry Reviews, 1999
5.
Luminescent Silver(I) and Copper(I) Systems Containing Pyridyl Phosphine Bridges
Crespo O., Gimeno M.C., Laguna A., Larraz C.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2009
6.
Cu(I) complexes – Thermally activated delayed fluorescence. Photophysical approach and material design
Czerwieniec R., Leitl M.J., Homeier H.H., Yersin H.
Coordination Chemistry Reviews, 2016
7.
Heteroleptic, Dinuclear Copper(I) Complexes for Application in Organic Light-Emitting Diodes
Zink D.M., Volz D., Baumann T., Mydlak M., Flügge H., Friedrichs J., Nieger M., Bräse S.
Chemistry of Materials, 2013
9.
Bluish-Green Cu(I) Dimers Chelated with Thiophene Ring-Introduced Diphosphine Ligands for Both Singlet and Triplet Harvesting in OLEDs.
Li X., Zhang J., Zhao Z., Yu X., Li P., Yao Y., Liu Z., Jin Q., Bian Z., Lu Z., Huang C.
ACS applied materials & interfaces, 2019
10.
Bright Coppertunities: Multinuclear CuIComplexes with N-P Ligands and Their Applications
Wallesch M., Volz D., Zink D.M., Schepers U., Nieger M., Baumann T., Bräse S.
Chemistry - A European Journal, 2014
11.
Luminescent Thermochromism in a Gold(I)–Copper(I) Phosphine–Pyridine Complex
Chen K., Catalano V.J.
European Journal of Inorganic Chemistry, 2015
12.
Unprecedented Luminescent Heteropolynuclear Aggregates with Gold Thiolates as Building Blocks
Crespo O., Gimeno M.C., Laguna A., Lahoz F.J., Larraz C.
Inorganic Chemistry, 2011
13.
Heteropolynuclear Gold Complexes with Metallophilic Interactions: Modulation of the Luminescent Properties
Calhorda M.J., Ceamanos C., Crespo O., Gimeno M.C., Laguna A., Larraz C., Vaz P.D., Villacampa M.D.
Inorganic Chemistry, 2010
14.
1,3-P,N hybrid ligands in mononuclear coordination chemistry and homogeneous catalysis
Rong M.K., Holtrop F., Slootweg J.C., Lammertsma K.
Coordination Chemistry Reviews, 2019
15.
Dramatic Rate Acceleration by a Diphenyl-2-pyridylphosphine Ligand in the Hydration of Nitriles Catalyzed by Ru(acac)2 Complexes
Oshiki T., Yamashita H., Sawada K., Utsunomiya M., Takahashi K., Takai K.
Organometallics, 2005
16.
Pyridylphosphines
Newkome G.R.
Chemical Reviews, 1993
17.
SYNTHESIS AND STRUCTURE OF A BINUCLEAR Pd(II) CHLORANILATE COMPLEX
Romashev N.F., Bakaev I.V., Komlyagina V.I., Fomenko I.S., Laricheva Y.A., Petrov P.A., Gushchin A.L.
Journal of Structural Chemistry, 2021
18.
Efficient palladium catalysts for the carbonylation of alkynes
Drent E., Arnoldy P., Budzelaar P.H.
Journal of Organometallic Chemistry, 1993
19.
Synthesis of novel pyridyl containing phospholanes and their polynuclear luminescent copper(i) complexes.
Musina E.I., Shamsieva A.V., Strelnik I.D., Gerasimova T.P., Krivolapov D.B., Kolesnikov I.E., Grachova E.V., Tunik S.P., Bannwarth C., Grimme S., Katsyuba S.A., Karasik A.A., Sinyashin O.G.
Dalton Transactions, 2016
20.
Cu(I) Complexes of Multidentate N,C,N- and P,C,P-Carbodiphosphorane Ligands and Their Photoluminescence
Klein M., Demirel N., Schinabeck A., Yersin H., Sundermeyer J.
Molecules, 2020
21.
Assembly of Heterometallic AuICu2I2Cores on the Scaffold of NPPN-Bridging Cyclic Bisphosphine
Dayanova I.R., Shamsieva A.V., Strelnik I.D., Gerasimova T.P., Kolesnikov I.E., Fayzullin R.R., Islamov D.R., Saifina A.F., Musina E.I., Hey-Hawkins E., Karasik A.A.
Inorganic Chemistry, 2021
22.
Controllable Synthesis and Luminescence Behavior of Tetrahedral Au@Cu4 and Au@Ag4 Clusters Supported by tris(2-Pyridyl)phosphine
Baranov A.Y., Slavova S.O., Berezin A.S., Petrovskii S.K., Samsonenko D.G., Bagryanskaya I.Y., Fedin V.P., Grachova E.V., Artem’ev A.V.
Inorganic Chemistry, 2022
23.
An Alternative Host Material for Long-Lifespan Blue Organic Light-Emitting Diodes Using Thermally Activated Delayed Fluorescence
Ihn S., Lee N., Jeon S.O., Sim M., Kang H., Jung Y., Huh D.H., Son Y.M., Lee S.Y., Numata M., Miyazaki H., Gómez-Bombarelli R., Aguilera-Iparraguirre J., Hirzel T., Aspuru-Guzik A., et. al.
Advanced Science, 2017
24.
Trigonal Planar Au@Ag 3 Clusters Showing Exceptionally Fast and Efficient Phosphorescence in Violet to Deep‐Blue Region
Artem'ev A.V., Baranov A.Y., Berezin A.S., Lapteva U.A., Samsonenko D.G., Bagryanskaya I.Y.
Chemistry - A European Journal, 2022
26.
Multidentate 2-pyridyl-phosphine ligands – towards ligand tuning and chirality
Hanf S., García-Rodríguez R., Feldmann S., Bond A.D., Hey-Hawkins E., Wright D.S.
Dalton Transactions, 2017
27.
[1,2-Bis(diphenylphosphanyl)ethane-κ2P,P′]dichloridopalladium(II) dimethyl sulfoxide monosolvate
Warad I., Aldwayyan A.S., Al-Jekhedab F.M., Choudhary M.I., Yousuf S.
Acta Crystallographica Section E Structure Reports Online, 2012
28.
Dinuclear and tetranuclear copper(I) iodide complexes with P and P^N donor ligands: Structural and photoluminescence studies
Neshat A., Aghakhanpour R.B., Mastrorilli P., Todisco S., Molani F., Wojtczak A.
Polyhedron, 2018
30.
Architecture and synthesis of P,N-heterocyclic phosphine ligands
Munzeiwa W.A., Omondi B., Nyamori V.O.
Beilstein Journal of Organic Chemistry, 2020
31.
Singlet harvesting copper-based emitters: a modular approach towards next-generation OLED technology
Zink D.M., Bergmann L., Ambrosek D., Wallesch M., Volz D., Mydlak M.
Translational Materials Research, 2014
32.
Sukhikh T.S., Davydova M.P., Artem'ev A.V.
Mendeleev Communications, 2023
33.
Hydrogenation of biomass derivate catalysed by ruthenium (II) complexes containing phosphorus-nitrogen ligands under mild conditions
Valdebenito G., Parra-Melipan S., Dinamarca C.F., López V., Vega A., Abarca G., Aguirre P.
Molecular Catalysis, 2023
34.
Heterometallic Au(I)–Cu(I) Clusters: Luminescence Studies and 1O2 Production
Romo-Islas G., Ward J.S., Rissanen K., Rodríguez L.
Inorganic Chemistry, 2023
38.
Davydova M.P., Sukhikh T.S., Artem’ev A.V.
Mendeleev Communications, 2024