Issue 44, 2023

2-(Thienyl)quinoxaline derivatives and their application in Ir(iii) complexes yielding tuneable deep red emitters

Abstract

The synthesis and characterisation of eleven different 2-(thienyl)quinoxaline species that incorporate different points of functionality, including at the thiophene or quinoxaline rings, are described. These species display variable fluorescence properties in the visible region (λem = 401–491 nm) depending upon the molecular structures and extent of conjugation. The series of 2-(thienyl)quinoxaline species were then investigated as cyclometalating agents for Ir(III) to yield [Ir(C^N)2(bipy)]PF6 (where C^N = the cyclometalated ligand; bipy = 2,2′-bipyridine). Eight complexes were successfully isolated and fully characterised by an array of spectroscopic and analytical techniques. Two Ir(III) examples were structurally characterised in the solid state using single crystal X-ray diffraction; both structures confirmed the proposed formulations and coordination spheres in each case showing that the thiophene coordinates via a Ir–C bond. The photophysical properties of the complexes revealed that each complex is luminescent under ambient conditions with a range of emission wavelengths observed (665–751 nm) indicating that electronic tuning can be achieved via both the thienyl and quinoxaline moieties.

Graphical abstract: 2-(Thienyl)quinoxaline derivatives and their application in Ir(iii) complexes yielding tuneable deep red emitters

Supplementary files

Article information

Article type
Paper
Submitted
12 Jul 2023
Accepted
19 Oct 2023
First published
24 Oct 2023
This article is Open Access
Creative Commons BY license

Dalton Trans., 2023,52, 16480-16491

2-(Thienyl)quinoxaline derivatives and their application in Ir(III) complexes yielding tuneable deep red emitters

S. A. Fitzgerald, E. N. Payce, P. N. Horton, S. J. Coles and S. J. A. Pope, Dalton Trans., 2023, 52, 16480 DOI: 10.1039/D3DT02193A

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