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

Dalton Transactions

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
Online Access: Check full text

URI: https://cronfa.swan.ac.uk/Record/cronfa68128
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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.

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