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Cyrene™ as a green alternative to N,N′-dimethylformamide (DMF) in the synthesis of MLCT-emissive ruthenium(ii) polypyridyl complexes for biological applications

Steffan D. James, Christopher E. Elgar Orcid Logo, Dandan Chen Orcid Logo, Matthew I. Lewis, Elias T. L. Ash, Dominic S. Conway, Benjamin J. Tuckley, Leigh E. Phillips Orcid Logo, Natália Kolozsvári, Xiaohe Tian Orcid Logo, Martin Gill Orcid Logo

Dalton Transactions, Volume: 53, Issue: 46, Pages: 18506 - 18514

Swansea University Author: Martin Gill Orcid Logo

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DOI (Published version): 10.1039/d4dt02676d

Abstract

Ruthenium(II) polypyridyl complexes (RPCs) that emit from triplet metal to ligand charge transfer (MLCT) states find a wide variety of uses ranging from luminophores to potential anti-cancer or anti-bacterial therapeutics. Herein we describe a greener, microwave-assisted synthetic pathway for the pr...

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Published in: Dalton Transactions
ISSN: 1477-9226 1477-9234
Published: Royal Society of Chemistry (RSC) 2024
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URI: https://cronfa.swan.ac.uk/Record/cronfa68128
Abstract: Ruthenium(II) polypyridyl complexes (RPCs) that emit from triplet metal to ligand charge transfer (MLCT) states find a wide variety of uses ranging from luminophores to potential anti-cancer or anti-bacterial therapeutics. Herein we describe a greener, microwave-assisted synthetic pathway for the preparation of homoleptic [Ru(N^N)3]2+ and bis-heteroleptic [Ru(N^N)2(N^N)]2+ type complexes. This employs the bio-renewable solvent CyreneTM, dihydrolevoglucosenone, as a green alternative to N,N’-dimethylformamide (DMF) in the synthesis of Ru(N^N)2Cl2 intermediate complexes, obtaining comparable yields for N^N = 2,2’-bipyridine, 1,10-phenanthroline and methylated derivatives. Employing these intermediates, a range of RPCs were prepared and we verify that the ubiquitous luminophore [Ru(bpy)3]2+ (bpy = 2,2’-bipyridine) can be prepared by this two-step green pathway where it is virtually indistinguishable from a commercial reference. Furthermore, the novel complexes [Ru(bpy)2(10,11-dmdppz)]2+ (10,11-dmdppz = 10,11-dimethyl-dipyridophenazine) and [Ru(5,5’-dmbpy)2(10,11-dmdppz)]2+ (5,5’-dmbpy = 5,5’-dimethyl-bpy) intercalate duplex DNA with high affinity (DNA binding constants, Kb = 5.7 x107 and 1.0x107 M-1, respectively) and function as plasma membrane and nuclear DNA dyes for confocal and STED microscopies courtesy of their long-lived MLCT luminescence.
College: Faculty of Science and Engineering
Funders: This work was supported by Royal Society of Chemistry (RSC) Research Fund and Research Enablement grants (R20-8717 and E21-9540096197) and the National Natural Science Foundation of China (32171361). We thank the James Pantyfedwen Foundation for a scholarship to SJ.
Issue: 46
Start Page: 18506
End Page: 18514

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