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Special Issue "Ruthenium Complex"

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A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (28 February 2014)

Special Issue Editors

Guest Editor
Prof. Dr. Albert Demonceau (Website)

University of Liège, Department of Chemistry, Sart-Tilman (B.6a), 4000 Liège, Belgium
Interests: macromolecular chemistry; organometallic synthesis; homogeneous catalysis; carbon-carbon bond formation; ruthenium-arene complexes
Guest Editor
Prof. Dr. Ileana Dragutan

Institute of Organic Chemistry of the Romanian Academy, 202B Spl. Independentei, 060023 Bucharest, P.O. Box 35-108, Romania
Interests: transition metals complexes and their chemistry and use in homogeneous catalysis and polymer synthesis; Ru-catalyzed olefin metathesis; metathesis driven syntheses of some bioactive compounds and metathesis-related processes; stable nitroxide free radicals and their preparation and multifarious applications using ESR
Guest Editor
Prof. Dr. Valerian Dragutan

Institute of Organic Chemistry of the Romanian Academy, 202B Spl. Independentei, 060023 Bucharest, P.O. Box 35-108, Romania
Phone: +4021-316-79.00
Interests: organic synthesis; natural compounds; heterocyclic compounds; reactive organometallic and coordination compounds; bioactive organotin; transition metal complexes; asymmetric catalysis; stereoselective Ziegler-Natta polymerization; organometallic polymers

Special Issue Information

Dear Colleagues,

This hot topic issue of Molecules covers challenging aspects on the design and application of a broad series of ruthenium complexes in catalysis, synthesis of bioactive organic and organometallic compounds, unnatural and natural compounds of biological relevance, chemotherapeutic treatment, supra-molecular chemistry, and materials sciences. Special attention is devoted to recent developments in the synthesis and characterization of coordination and organometallic ruthenium compounds, as well as to selected chemical transformations promoted by highly active and chemo-selective ruthenium-based catalytic systems. Such transformations include C-H and C-X bond activation, hydrogenation and hydrogen transfer reactions, oxidation and hydroxylation, olefin metathesis and related C-C coupling reactions, and isomerization, oligomerization, and polymerization reactions. Topics will be devoted to novel mono- and bi-nuclear ruthenium compounds, complexes with diverse chiral ligands, and ruthenium antitumor agents. Cutting-edge applications in biology and medicine, catalysis, materials science, petrochemicals, and agrochemicals will be covered while disclosing the most relevant trends in future development.

Prof. Dr. Albert Demonceau
Prof. Dr. Ileana Dragutan
Prof. Dr. Valerian Dragutan
Guest Editors

Submission

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are refereed through a peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed Open Access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs).


Keywords

  • anti-tumor agents
  • aqueous ruthenium systems
  • arene ligands
  • bioactive compounds
  • bi-nuclear complexes
  • cage compounds
  • carborane complexes
  • cellular interactions
  • chemotherapeutic treatment
  • chiral complexes
  • dendritic molecules
  • DNA-binding
  • homogeneous catalysis
  • immobilized catalysts
  • N-heterocyclic carbenes
  • porphyrine-ruthenium complexes
  • macro-molecular structures
  • supra-molecular assemblies

Published Papers (11 papers)

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Research

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Open AccessArticle An Unusual Conversion of Paramagnetic [3-Cl-3,3,8-{Ph2P(CH2)nPPh-µ-(C6H4-ortho)}-1,2-(CH3)2-closo-3,1,2-RuIIIC2B9H8] (n = 3 and 4) to Form the First 18-Electron P-Phenylene ortho-Cycloboronated closo-Ruthenacarboranes with a Dioxygen Ligand
Molecules 2014, 19(6), 7094-7103; doi:10.3390/molecules19067094
Received: 21 April 2014 / Revised: 16 May 2014 / Accepted: 22 May 2014 / Published: 30 May 2014
PDF Full-text (565 KB) | HTML Full-text | XML Full-text
Abstract
Treatment of [3-Cl-3,3,8-[Ph2P(CH2)nPPh-µ-(C6H4-ortho)]-1,2-Me2-closo-3,1,2-RuIIIC2B9H8] (1, n = 3; 2, n = 4) with an excess of [...] Read more.
Treatment of [3-Cl-3,3,8-[Ph2P(CH2)nPPh-µ-(C6H4-ortho)]-1,2-Me2-closo-3,1,2-RuIIIC2B9H8] (1, n = 3; 2, n = 4) with an excess of KOH in a 1:1 benzene/methanol mixture at room temperature in air affords new dioxygen closo-ruthenacarborane complexes [3-(η2-O2)-3,3,8-[Ph2P(CH2)nPPh-µ-(C6H4-ortho)]-1,2-Me2-closo-3,1,2-RuIIIC2B9H8] (3, n = 3) and (4, n = 4) in 42.5% and 45.8% yield respectively. The structures of dioxygen complexes 3 and 4 were established by single-crystal X-ray diffraction. The IR and multinuclear NMR data [1H, 13C{1H}, 31P{1H} and 11B{1H}] along with 2D HSQC correlation spectra for the new dioxygen closo-ruthenacarboranes are discussed. Full article
(This article belongs to the Special Issue Ruthenium Complex)
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Open AccessArticle Nanostructured Lipid Systems as a Strategy to Improve the in Vitro Cytotoxicity of Ruthenium(II) Compounds
Molecules 2014, 19(5), 5999-6008; doi:10.3390/molecules19055999
Received: 1 March 2014 / Revised: 26 April 2014 / Accepted: 4 May 2014 / Published: 9 May 2014
Cited by 2 | PDF Full-text (219 KB) | HTML Full-text | XML Full-text
Abstract
Tuberculosis is an ancient disease that is still present as a global public health problem. Our group has been investigating new molecules with anti-TB activity. In this context, inorganic chemistry has been a quite promising source of such molecules, with excellent results [...] Read more.
Tuberculosis is an ancient disease that is still present as a global public health problem. Our group has been investigating new molecules with anti-TB activity. In this context, inorganic chemistry has been a quite promising source of such molecules, with excellent results seen with ruthenium compounds. Nanostructured lipid systems may potentiate the action of drugs by reducing the required dosage and side effects and improving the antimicrobial effects. The aim of this study was to develop a nanostructured lipid system and then characterize and apply these encapsulated compounds (SCARs 1, 2 and 4) with the goal of improving their activity by decreasing the Minimum Inhibitory Concentration (MIC90) and reducing the cytotoxicity (IC50). The nanostructured system was composed of 10% phase oil (cholesterol), 10% surfactant (soy oleate, soy phosphatidylcholine and Eumulgin®) and 80% aqueous phase (phosphate buffer pH = 7.4). Good activity against Mycobacterium tuberculosis was maintained after the incorporation of the compounds into the nanostructured lipid system, while the cytotoxicity decreased dramatically, in some cases up to 20 times less toxic than the unencapsulated drug. Full article
(This article belongs to the Special Issue Ruthenium Complex)
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Open AccessArticle Improved Metathesis Lifetime: Chelating Pyridinyl-Alcoholato Ligands in the Second Generation Grubbs Precatalyst
Molecules 2014, 19(5), 5522-5537; doi:10.3390/molecules19055522
Received: 16 March 2014 / Revised: 22 April 2014 / Accepted: 24 April 2014 / Published: 29 April 2014
Cited by 2 | PDF Full-text (1081 KB) | HTML Full-text | XML Full-text
Abstract
Hemilabile ligands can release a free coordination site “on demand” of an incoming nucleophilic substrate while occupying it otherwise. This is believed to increase the thermal stability and activity of catalytic systems and therefore prevent decomposition via free coordination sites. In this [...] Read more.
Hemilabile ligands can release a free coordination site “on demand” of an incoming nucleophilic substrate while occupying it otherwise. This is believed to increase the thermal stability and activity of catalytic systems and therefore prevent decomposition via free coordination sites. In this investigation chelating pyridinyl-alcoholato ligands were identified as possible hemilabile ligands for incorporation into the second generation Grubbs precatalyst. The O,N-alcoholato ligands with different steric bulk could be successfully incorporated into the precatalysts. The incorporation of the sterically hindered, hemilabile O,N-ligands improved the thermal stability, activity, selectivity and lifetime of these complexes towards the metathesis of 1-octene. A decrease in the activity of the second generation Grubbs precatalyst was additionally observed after incorporating a hemilabile O,N-ligand with two phenyl groups into the system, while increasing their lifetime. Full article
(This article belongs to the Special Issue Ruthenium Complex)
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Open AccessArticle In Vitro Studies of the Activity of Dithiocarbamate Organoruthenium Complexes against Clinically Relevant Fungal Pathogens
Molecules 2014, 19(4), 5402-5420; doi:10.3390/molecules19045402
Received: 26 February 2014 / Revised: 17 April 2014 / Accepted: 22 April 2014 / Published: 24 April 2014
Cited by 2 | PDF Full-text (408 KB) | HTML Full-text | XML Full-text
Abstract
The in vitro antifungal activity of nine dirutheniumpentadithiocarbamate complexes C1C9 was investigated and assessed for its activity against four different fungal species with clinical interest and related to invasive fungal infections (IFIs), such as Candida spp. [C. albicans (two [...] Read more.
The in vitro antifungal activity of nine dirutheniumpentadithiocarbamate complexes C1C9 was investigated and assessed for its activity against four different fungal species with clinical interest and related to invasive fungal infections (IFIs), such as Candida spp. [C. albicans (two clinical isolates), C. glabrata, C. krusei, C. parapsolisis, C. tropicalis, C.dubliniensis (six clinical isolates)], Paracoccidioides brasiliensis (seven clinical isolates), Cryptococcus neoformans and Sporothrix schenckii. All synthesized complexes C1C9 and also the free ligands L1L9 were submitted to in vitro tests against those fungi and the results are very promising, since some of the obtained MIC (minimal inhibitory concentration) values were very low (from 10−6 mol mL−1 to 10−8 mol mL−1) against all investigated clinically relevant fungal pathogens, except for C. glabrata, that the MIC values are close to the ones obtained for fluconazole, the standard antifungal agent tested. Preliminary structure-activity relations (SAR) might be suggested and a strong influence from steric and lipophilic parameters in the antifungal activity can be noticed. Cytotoxicity assays (IC50) showed that the complexes are not as toxic (IC50 values are much higher—30 to 200 fold—than MIC values). These ruthenium complexes are very promising lead compounds for novel antifungal drug development, especially in IFIs, one of most harmful emerging infection diseases (EIDs). Full article
(This article belongs to the Special Issue Ruthenium Complex)
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Review

Jump to: Research

Open AccessReview Editorial of Special Issue Ruthenium Complex: The Expanding Chemistry of the Ruthenium Complexes
Molecules 2015, 20(9), 17244-17274; doi:10.3390/molecules200917244
Received: 6 August 2015 / Revised: 9 September 2015 / Accepted: 11 September 2015 / Published: 18 September 2015
Cited by 5 | PDF Full-text (763 KB) | HTML Full-text | XML Full-text
Abstract Recent trends in Ru complex chemistry are surveyed with emphasis on the development of anticancer drugs and applications in catalysis, polymers, materials science and nanotechnology. Full article
(This article belongs to the Special Issue Ruthenium Complex)
Open AccessReview Towards the Development of Functionalized PolypyridineLigands for Ru(II) Complexes as Photosensitizers inDye-Sensitized Solar Cells (DSSCs)
Molecules 2014, 19(8), 12421-12460; doi:10.3390/molecules190812421
Received: 22 July 2014 / Revised: 4 August 2014 / Accepted: 12 August 2014 / Published: 15 August 2014
Cited by 6 | PDF Full-text (534 KB) | HTML Full-text | XML Full-text
Abstract
A number of novel ruthenium(II) polypyridine complexes have been designedand synthesized for use as photosensitizers in dye-sensitized solar cells (DSSCs) due totheir rich photophysical properties such as intense absorption, long-lived lifetimes, highemission quantum yields and unique redox characteristics. Many of these complexesexhibit [...] Read more.
A number of novel ruthenium(II) polypyridine complexes have been designedand synthesized for use as photosensitizers in dye-sensitized solar cells (DSSCs) due totheir rich photophysical properties such as intense absorption, long-lived lifetimes, highemission quantum yields and unique redox characteristics. Many of these complexesexhibit photophysical behavior that can be readily controlled through a careful choice ofligands and/or substituents. With this perspective, we review the design and general syntheticmethods of some polypyridine ligands based on bipyridine, phenanthroline, terpyridine andquaterpyridine with/without anchoring groups with a view to correlate functionality ofligand structures with the observed photophysical, electroredox and power conversionefficiency of some examples of Ru(II) polypyridyl complexes that have been reported andparticularly used in the DSSCs applications. The main interest, however, is focused onshowing the development of new polypyridine ligand materials containing long-rangeelectron transfer motifs such as the alkenyl, alkynyl and polyaromatic donor functionalities. Full article
(This article belongs to the Special Issue Ruthenium Complex)
Open AccessReview Ruthenium Complexes as NO Donors for Vascular Relaxation Induction
Molecules 2014, 19(7), 9628-9654; doi:10.3390/molecules19079628
Received: 8 April 2014 / Revised: 9 June 2014 / Accepted: 26 June 2014 / Published: 7 July 2014
Cited by 9 | PDF Full-text (1534 KB) | HTML Full-text | XML Full-text
Abstract
Nitric oxide (NO) donors are substances that can release NO. Vascular relaxation induction is among the several functions of NO, and the administration of NO donors is a pharmacological alternative to treat hypertension. This review will focus on the physicochemical description of [...] Read more.
Nitric oxide (NO) donors are substances that can release NO. Vascular relaxation induction is among the several functions of NO, and the administration of NO donors is a pharmacological alternative to treat hypertension. This review will focus on the physicochemical description of ruthenium-derived NO donor complexes that release NO via reduction and light stimulation. In particular, we will discuss the complexes synthesized by our research group over the last ten years, and we will focus on the vasodilation and arterial pressure control elicited by these complexes. Soluble guanylyl cyclase (sGC) and potassium channels are the main targets of the NO species released from the inorganic compounds. We will consider the importance of the chemical structure of the ruthenium complexes and their vascular effects. Full article
(This article belongs to the Special Issue Ruthenium Complex)
Open AccessReview Experimental and Theoretical Perspectives of the Noyori-Ikariya Asymmetric Transfer Hydrogenation of Imines
Molecules 2014, 19(6), 6987-7007; doi:10.3390/molecules19066987
Received: 28 February 2014 / Revised: 13 May 2014 / Accepted: 21 May 2014 / Published: 28 May 2014
Cited by 7 | PDF Full-text (596 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The asymmetric transfer hydrogenation (ATH) of imines catalyzed by the Noyori-Ikariya [RuCl(η6-arene)(N-arylsulfonyl-DPEN)] (DPEN = 1,2-diphenylethylene-1,2-diamine) half-sandwich complexes is a research topic that is still being intensively developed. This article focuses on selected aspects of this catalytic system. [...] Read more.
The asymmetric transfer hydrogenation (ATH) of imines catalyzed by the Noyori-Ikariya [RuCl(η6-arene)(N-arylsulfonyl-DPEN)] (DPEN = 1,2-diphenylethylene-1,2-diamine) half-sandwich complexes is a research topic that is still being intensively developed. This article focuses on selected aspects of this catalytic system. First, a great deal of attention is devoted to the N-arylsulfonyl moiety of the catalysts in terms of its interaction with protonated imines (substrates) and amines (components of the hydrogen-donor mixture). The second part is oriented toward the role of the η6-coordinated arene. The final part concerns the imine substrate structural modifications and their importance in connection with ATH. Throughout the text, the summary of known findings is complemented with newly-presented ones, which have been approached both experimentally and computationally. Full article
(This article belongs to the Special Issue Ruthenium Complex)
Open AccessReview Ruthenium Tetroxide and Perruthenate Chemistry. Recent Advances and Related Transformations Mediated by Other Transition Metal Oxo-species
Molecules 2014, 19(5), 6534-6582; doi:10.3390/molecules19056534
Received: 24 February 2014 / Revised: 14 May 2014 / Accepted: 16 May 2014 / Published: 21 May 2014
Cited by 12 | PDF Full-text (519 KB) | HTML Full-text | XML Full-text
Abstract
In the last years ruthenium tetroxide is increasingly being used in organic synthesis. Thanks to the fine tuning of the reaction conditions, including pH control of the medium and the use of a wider range of co-oxidants, this species has proven to [...] Read more.
In the last years ruthenium tetroxide is increasingly being used in organic synthesis. Thanks to the fine tuning of the reaction conditions, including pH control of the medium and the use of a wider range of co-oxidants, this species has proven to be a reagent able to catalyse useful synthetic transformations which are either a valuable alternative to established methods or even, in some cases, the method of choice. Protocols for oxidation of hydrocarbons, oxidative cleavage of C–C double bonds, even stopping the process at the aldehyde stage, oxidative cleavage of terminal and internal alkynes, oxidation of alcohols to carboxylic acids, dihydroxylation of alkenes, oxidative degradation of phenyl and other heteroaromatic nuclei, oxidative cyclization of dienes, have now reached a good level of improvement and are more and more included into complex synthetic sequences. The perruthenate ion is a ruthenium (VII) oxo-species. Since its introduction in the mid-eighties, tetrapropylammonium perruthenate (TPAP) has reached a great popularity among organic chemists and it is mostly employed in catalytic amounts in conjunction with N-methylmorpholine N-oxide (NMO) for the mild oxidation of primary and secondary alcohols to carbonyl compounds. Its use in the oxidation of other functionalities is known and recently, its utility in new synthetic transformations has been demonstrated. New processes, synthetic applications, theoretical studies and unusual transformations, published in the last eight years (2006–2013), in the chemistry of these two oxo-species, will be covered in this review with the aim of offering a clear picture of their reactivity. When appropriate, related oxidative transformations mediated by other metal oxo-species will be presented to highlight similarities and differences. An historical overview of some aspects of the ruthenium tetroxide chemistry will be presented as well. Full article
(This article belongs to the Special Issue Ruthenium Complex)
Open AccessReview RutheniumII Complexes bearing Fused Polycyclic Ligands: From Fundamental Aspects to Potential Applications
Molecules 2014, 19(4), 5028-5087; doi:10.3390/molecules19045028
Received: 28 February 2014 / Revised: 15 April 2014 / Accepted: 16 April 2014 / Published: 22 April 2014
Cited by 6 | PDF Full-text (1408 KB) | HTML Full-text | XML Full-text
Abstract
In this review, we first discuss the photophysics reported in the literature for mononuclear ruthenium complexes bearing ligands with extended aromaticity such as dipyrido[3,2-a:2',3'-c]phenazine (DPPZ), tetrapyrido[3,2-a:2',3'-c:3'',2''-h:2''',3'''-j]-phenazine (TPPHZ),  tetrapyrido[3,2-a:2',3'-c:3'',2''-h:2''',3'''-j]acridine (TPAC), 1,10-phenanthrolino[5,6-b]1,4,5,8,9,12-hexaazatriphenylene (PHEHAT) 9,11,20,22-tetraaza- tetrapyrido[3,2-a:2',3'-c:3'',2''-l:2''',3'''-n]pentacene (TATPP), etc. Photophysical properties of binuclear and polynuclear complexes [...] Read more.
In this review, we first discuss the photophysics reported in the literature for mononuclear ruthenium complexes bearing ligands with extended aromaticity such as dipyrido[3,2-a:2',3'-c]phenazine (DPPZ), tetrapyrido[3,2-a:2',3'-c:3'',2''-h:2''',3'''-j]-phenazine (TPPHZ),  tetrapyrido[3,2-a:2',3'-c:3'',2''-h:2''',3'''-j]acridine (TPAC), 1,10-phenanthrolino[5,6-b]1,4,5,8,9,12-hexaazatriphenylene (PHEHAT) 9,11,20,22-tetraaza- tetrapyrido[3,2-a:2',3'-c:3'',2''-l:2''',3'''-n]pentacene (TATPP), etc. Photophysical properties of binuclear and polynuclear complexes based on these extended ligands are then reported. We finally develop the use of binuclear complexes with extended π-systems for applications such as photocatalysis. Full article
(This article belongs to the Special Issue Ruthenium Complex)
Open AccessReview Magnetically Recoverable Ruthenium Catalysts in Organic Synthesis
Molecules 2014, 19(4), 4635-4653; doi:10.3390/molecules19044635
Received: 24 February 2014 / Revised: 1 April 2014 / Accepted: 10 April 2014 / Published: 15 April 2014
Cited by 13 | PDF Full-text (488 KB) | HTML Full-text | XML Full-text
Abstract
Magnetically recyclable catalysts with magnetic nanoparticles (MNPs) are becoming a major trend towards sustainable catalysts. In this area, recyclable supported ruthenium complexes and ruthenium nanoparticles occupy a key place and present great advantages compared to classic catalysts. In this micro-review, attention is [...] Read more.
Magnetically recyclable catalysts with magnetic nanoparticles (MNPs) are becoming a major trend towards sustainable catalysts. In this area, recyclable supported ruthenium complexes and ruthenium nanoparticles occupy a key place and present great advantages compared to classic catalysts. In this micro-review, attention is focused on the fabrication of MNP-supported ruthenium catalysts and their catalytic applications in various organic syntheses. Full article
(This article belongs to the Special Issue Ruthenium Complex)

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