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Issue 20, 2020
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Luminescent organic dyes containing a phenanthro[9,10-D]imidazole core and [Ir(N^C)(N^N)]+ complexes based on the cyclometalating and diimine ligands of this type

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Abstract

A family of diimine (N^N) and cyclometalating (N^C) ligands based on a phenanthro-imidazole aromatic system: 2-pyridyl-1H-phenanthro[9,10-d]imidazole (N^N); 2-R-1-phenyl-1H-phenanthro[9,10-d]imidazole, R = phenyl (N^C4), 3-iodophenyl (N^C5) and 4-nitrophenyl (N^C6) were prepared. It was found that N^C4 and N^C5 show π–π* fluorescence typical of aromatic systems of this sort, whereas the donor–acceptor architecture of N^C6 leads to strong emission solvatochromism and acidochromism, indicating the charge transfer character of the fluorescence observed. Six iridium(III) complexes (1–6) [Ir(N^C#)2(N^N)]+, where # = 1–6 and N^C1 = 2-phenylpyridine, N^C2 = 2-(benzo[b]thiophen-2-yl)pyridine, and N^C3 = methyl 2-phenylquinoline-4-carboxylate, were also synthesized and characterized. The complexes obtained display moderate to bright phosphorescence with quantum yields up to 46% in degassed solution. The photophysical characteristics of 1–6 were studied in detail. DFT and TD DFT calculations were used for the assignment of electronic transitions responsible for the absorption and emission of these compounds. The variations in the cyclometalating ligand structure give rise to rich photophysics of the complexes obtained. It was found that the orbitals of both N^C and N^N ligands make a major contribution to the formation of emissive excited states and a delicate balance between the energy of the ligands’ frontier orbitals determines the emission character.

Graphical abstract: Luminescent organic dyes containing a phenanthro[9,10-D]imidazole core and [Ir(N^C)(N^N)]+ complexes based on the cyclometalating and diimine ligands of this type

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Supplementary files

Article information


Submitted
15 Feb 2020
Accepted
14 Apr 2020
First published
14 Apr 2020

Dalton Trans., 2020,49, 6751-6763
Article type
Paper

Luminescent organic dyes containing a phenanthro[9,10-D]imidazole core and [Ir(N^C)(N^N)]+ complexes based on the cyclometalating and diimine ligands of this type

A. I. Solomatina, K. M. Kuznetsov, V. V. Gurzhiy, V. V. Pavlovskiy, V. V. Porsev, R. A. Evarestov and S. P. Tunik, Dalton Trans., 2020, 49, 6751
DOI: 10.1039/D0DT00568A

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