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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
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URI: https://cronfa.swan.ac.uk/Record/cronfa68128
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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.</abstract><type>Journal Article</type><journal>Dalton Transactions</journal><volume/><journalNumber/><paginationStart/><paginationEnd/><publisher>Royal Society of Chemistry (RSC)</publisher><placeOfPublication/><isbnPrint/><isbnElectronic/><issnPrint>1477-9226</issnPrint><issnElectronic>1477-9234</issnElectronic><keywords/><publishedDay>31</publishedDay><publishedMonth>10</publishedMonth><publishedYear>2024</publishedYear><publishedDate>2024-10-31</publishedDate><doi>10.1039/d4dt02676d</doi><url/><notes/><college>COLLEGE NANME</college><department>Engineering and Applied Sciences School</department><CollegeCode>COLLEGE CODE</CollegeCode><DepartmentCode>EAAS</DepartmentCode><institution>Swansea University</institution><apcterm>Another institution paid the OA fee</apcterm><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). 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spelling v2 68128 2024-10-31 CyreneTM as a green alternative to N,N’-dimethylformamide (DMF) in the synthesis of MLCT-emissive ruthenium(II) polypyridyl complexes for biological applications 485d85b532851e8863cd19c6af7e00f7 0000-0002-1371-5676 Martin Gill Martin Gill true false 2024-10-31 EAAS 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. Journal Article Dalton Transactions Royal Society of Chemistry (RSC) 1477-9226 1477-9234 31 10 2024 2024-10-31 10.1039/d4dt02676d COLLEGE NANME Engineering and Applied Sciences School COLLEGE CODE EAAS Swansea University Another institution paid the OA fee 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. 2024-11-06T14:40:58.9824398 2024-10-31T15:04:15.8062831 Faculty of Science and Engineering School of Engineering and Applied Sciences - Chemistry Steffan D James 1 Christopher E Elgar 2 Dandan Chen 3 Matthew I Lewis 4 Elias T. L. Ash 5 Dominic S Conway 6 Benjamin J. Tuckley 7 Leigh E Phillips 8 Natália Kolozsvári 9 Xiaohe Tian 10 Martin Gill 0000-0002-1371-5676 11 68128__32832__f23d7014b01a4c938a73daf25e6e35d9.pdf 68128.VOR.pdf 2024-11-04T13:10:04.8405417 Output 1152778 application/pdf Version of Record true © The Royal Society of Chemistry 2024. This Open Access Article is licensed under a Creative Commons Attribution 3.0 Unported Licence. true eng http://creativecommons.org/licenses/by/3.0/
title CyreneTM as a green alternative to N,N’-dimethylformamide (DMF) in the synthesis of MLCT-emissive ruthenium(II) polypyridyl complexes for biological applications
spellingShingle CyreneTM as a green alternative to N,N’-dimethylformamide (DMF) in the synthesis of MLCT-emissive ruthenium(II) polypyridyl complexes for biological applications
Martin Gill
title_short CyreneTM as a green alternative to N,N’-dimethylformamide (DMF) in the synthesis of MLCT-emissive ruthenium(II) polypyridyl complexes for biological applications
title_full CyreneTM as a green alternative to N,N’-dimethylformamide (DMF) in the synthesis of MLCT-emissive ruthenium(II) polypyridyl complexes for biological applications
title_fullStr CyreneTM as a green alternative to N,N’-dimethylformamide (DMF) in the synthesis of MLCT-emissive ruthenium(II) polypyridyl complexes for biological applications
title_full_unstemmed CyreneTM as a green alternative to N,N’-dimethylformamide (DMF) in the synthesis of MLCT-emissive ruthenium(II) polypyridyl complexes for biological applications
title_sort CyreneTM as a green alternative to N,N’-dimethylformamide (DMF) in the synthesis of MLCT-emissive ruthenium(II) polypyridyl complexes for biological applications
author_id_str_mv 485d85b532851e8863cd19c6af7e00f7
author_id_fullname_str_mv 485d85b532851e8863cd19c6af7e00f7_***_Martin Gill
author Martin Gill
author2 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
format Journal article
container_title Dalton Transactions
publishDate 2024
institution Swansea University
issn 1477-9226
1477-9234
doi_str_mv 10.1039/d4dt02676d
publisher Royal Society of Chemistry (RSC)
college_str Faculty of Science and Engineering
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hierarchy_top_id facultyofscienceandengineering
hierarchy_top_title Faculty of Science and Engineering
hierarchy_parent_id facultyofscienceandengineering
hierarchy_parent_title Faculty of Science and Engineering
department_str School of Engineering and Applied Sciences - Chemistry{{{_:::_}}}Faculty of Science and Engineering{{{_:::_}}}School of Engineering and Applied Sciences - Chemistry
document_store_str 1
active_str 0
description 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.
published_date 2024-10-31T14:40:57Z
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