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Deep red emitting heteroleptic Ir(III) complexes that incorporate unsymmetrical 4-quinoline carboxylic acid derived ligands

Deep red emitting heteroleptic Ir(III) complexes that incorporate unsymmetrical 4-quinoline carboxylic acid derived ligands
Deep red emitting heteroleptic Ir(III) complexes that incorporate unsymmetrical 4-quinoline carboxylic acid derived ligands

Six disubstituted ligands based upon 2-(2′-pyridinyl/pyrazinyl)quinoline-4-carboxylic acids have been synthesised, solvent-free, in one step from a range of commercially available isatin derivatives. These species behave as ancillary chelating ligands for Ir(III) complexes of the form [Ir(C^N)2(N^N)]PF6 (where C^N=cyclometalating ligand; N^N=2-(2′-pyridinyl/pyrazinyl)quinoline-4-carboxylic acids). An X-ray crystallographic study on one complex shows a distorted octahedral geometry wherein a cis-C,C and trans-N,N coordination mode is observed for the cyclometalating ligands. DFT calculations predicted that variations in N^N ligand from 2,2′-bipyridine to L1–6 should localise the LUMO on to the Ln ligand and that the complexes are predicted to display MLCT/LLCT character. All complexes displayed luminescence in the deep red part of the visible region (674–679 nm) and emit from triplet states, but with little apparent tuning as a function of L1–6. Further time-resolved transient absorption spectroscopy supports the participation of these triplet states to the excited state character.

4-quinolinecarboxylic acid, cyclometalation, iridium, luminescence, synthesis
1434-1948
Elgar, Christopher E.
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Otaif, Haleema Y.
1b365536-1683-40d5-b6d2-3f869cdac579
Beames, Joseph M.
73b04545-4859-44ad-999e-551f82924c29
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Coles, Simon J.
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Hallett, Andrew J.
36cc4f6a-74d4-4894-8a65-8dd9d7803593
O'Kell, Sean P.
01ff0d06-c93a-455d-9586-c62b101eefc8
Pope, Simon J.A.
db9a489c-29ba-41cd-a96a-623bace0889d
Elgar, Christopher E.
f59426b7-72ba-4125-96e3-b9b63da790ff
Otaif, Haleema Y.
1b365536-1683-40d5-b6d2-3f869cdac579
Beames, Joseph M.
73b04545-4859-44ad-999e-551f82924c29
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hallett, Andrew J.
36cc4f6a-74d4-4894-8a65-8dd9d7803593
O'Kell, Sean P.
01ff0d06-c93a-455d-9586-c62b101eefc8
Pope, Simon J.A.
db9a489c-29ba-41cd-a96a-623bace0889d

Elgar, Christopher E., Otaif, Haleema Y., Beames, Joseph M., Horton, Peter N., Coles, Simon J., Hallett, Andrew J., O'Kell, Sean P. and Pope, Simon J.A. (2023) Deep red emitting heteroleptic Ir(III) complexes that incorporate unsymmetrical 4-quinoline carboxylic acid derived ligands. European Journal of Inorganic Chemistry, 26 (18), [e202300102]. (doi:10.1002/ejic.202300102).

Record type: Article

Abstract

Six disubstituted ligands based upon 2-(2′-pyridinyl/pyrazinyl)quinoline-4-carboxylic acids have been synthesised, solvent-free, in one step from a range of commercially available isatin derivatives. These species behave as ancillary chelating ligands for Ir(III) complexes of the form [Ir(C^N)2(N^N)]PF6 (where C^N=cyclometalating ligand; N^N=2-(2′-pyridinyl/pyrazinyl)quinoline-4-carboxylic acids). An X-ray crystallographic study on one complex shows a distorted octahedral geometry wherein a cis-C,C and trans-N,N coordination mode is observed for the cyclometalating ligands. DFT calculations predicted that variations in N^N ligand from 2,2′-bipyridine to L1–6 should localise the LUMO on to the Ln ligand and that the complexes are predicted to display MLCT/LLCT character. All complexes displayed luminescence in the deep red part of the visible region (674–679 nm) and emit from triplet states, but with little apparent tuning as a function of L1–6. Further time-resolved transient absorption spectroscopy supports the participation of these triplet states to the excited state character.

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Eur J Inorg Chem - 2023 - Elgar - Deep Red Emitting Heteroleptic Ir III Complexes that Incorporate Unsymmetrical - Version of Record
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Accepted/In Press date: 28 March 2023
e-pub ahead of print date: 11 April 2023
Published date: 23 June 2023
Additional Information: Funding Information: Cardiff University (Knowledge Economy Skills Scholarships to C.E.E.) and STG Aerospace are thanked for financial support. We thank the EPSRC UK National Crystallographic Service at the University of Southampton and the Chemistry Department, Jazan University, Saudi Arabia, for financial support and a scholarship to H.Y.O.
Keywords: 4-quinolinecarboxylic acid, cyclometalation, iridium, luminescence, synthesis

Identifiers

Local EPrints ID: 477509
URI: http://eprints.soton.ac.uk/id/eprint/477509
ISSN: 1434-1948
PURE UUID: 34974e1c-52dd-44d7-ad5f-4267636c8667
ORCID for Peter N. Horton: ORCID iD orcid.org/0000-0001-8886-2016
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 07 Jun 2023 16:59
Last modified: 18 Mar 2024 02:51

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Contributors

Author: Christopher E. Elgar
Author: Haleema Y. Otaif
Author: Joseph M. Beames
Author: Peter N. Horton ORCID iD
Author: Simon J. Coles ORCID iD
Author: Andrew J. Hallett
Author: Sean P. O'Kell
Author: Simon J.A. Pope

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