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Ruthenium Complex

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

Deadline for manuscript submissions: closed (28 February 2014) | Viewed by 105692

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Prof. Dr. Albert Demonceau

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

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Institute of Organic Chemistry of the Romanian Academy, 202B Spl. Independentei, 060023 Bucharest, 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
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Prof. Dr. Valerian Dragutan

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Institute of Organic Chemistry of the Romanian Academy, 202B Spl. Independentei, 060023 Bucharest, Romania
Interests: organic chemistry; organic synthesis; organometallic chemistry; coordination complexes; catalysis; free radicals; metathesis chemistry; polymerization chemistry
Special Issues, Collections and Topics in MDPI journals

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

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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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565 KiB

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-Ru^IIIC₂B₉H₈] (n = 3 and 4) to Form the First 18-Electron P-Phenylene ortho-Cycloboronated closo-Ruthenacarboranes with a Dioxygen Ligand

by Alexander Y. Kostukovich, Dmitrii I. D'yachihin, Fedor M. Dolgushin, Alexander F. Smol'yakov, Ivan A. Godovikov and Igor T. Chizhevsky

Molecules 2014, 19(6), 7094-7103; https://doi.org/10.3390/molecules19067094 - 30 May 2014

Cited by 7 | Viewed by 5255

Abstract

Treatment of [3-Cl-3,3,8-[Ph₂P(CH₂)_nPPh-µ-(C₆H₄-ortho)]-1,2-Me₂-closo-3,1,2-Ru^IIIC₂B₉H₈] (1, n = 3; 2, n = 4) with an excess of KOH [...] Read more.

Treatment of [3-Cl-3,3,8-[Ph₂P(CH₂)_nPPh-µ-(C₆H₄-ortho)]-1,2-Me₂-closo-3,1,2-Ru^IIIC₂B₉H₈] (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-Ru^IIIC₂B₉H₈] (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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219 KiB

Open AccessArticle

Nanostructured Lipid Systems as a Strategy to Improve the in Vitro Cytotoxicity of Ruthenium(II) Compounds

by Eduardo Sinesio De Freitas, Patricia Bento Da Silva, Marlus Chorilli, Alzir Azevedo Batista, Érica De Oliveira Lopes, Monize Martins da Silva, Clarice Queico Fujimura Leite and Fernando Rogério Pavan

Molecules 2014, 19(5), 5999-6008; https://doi.org/10.3390/molecules19055999 - 09 May 2014

Cited by 21 | Viewed by 6115

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 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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1081 KiB

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Improved Metathesis Lifetime: Chelating Pyridinyl-Alcoholato Ligands in the Second Generation Grubbs Precatalyst

by Jean I. Du Toit, Margaritha Jordaan, Carlijn A. A. Huijsmans, Johannes H. L. Jordaan, Cornelia G. C. E. Van Sittert and Hermanus C. M. Vosloo

Molecules 2014, 19(5), 5522-5537; https://doi.org/10.3390/molecules19055522 - 29 Apr 2014

Cited by 14 | Viewed by 5550

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 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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408 KiB

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In Vitro Studies of the Activity of Dithiocarbamate Organoruthenium Complexes against Clinically Relevant Fungal Pathogens

by Claudio L. Donnici, Luciano J. Nogueira, Maria Helena Araujo, Sheila Rodrigues Oliveira, Thais F. F. Magalhães, Miriam T. P. Lopes, Ana Cândida Araújo e Silva, Ana Maria da Costa Ferreira, Cleide V. B. Martins and Maria A. De Resende Stoianoff

Molecules 2014, 19(4), 5402-5420; https://doi.org/10.3390/molecules19045402 - 24 Apr 2014

Cited by 12 | Viewed by 7146

Abstract

The in vitro antifungal activity of nine dirutheniumpentadithiocarbamate complexes C1–C9 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 C1–C9 and also the free ligands L1–L9 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

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763 KiB

Open AccessReview

Editorial of Special Issue Ruthenium Complex: The Expanding Chemistry of the Ruthenium Complexes

by Ileana Dragutan, Valerian Dragutan and Albert Demonceau

Molecules 2015, 20(9), 17244-17274; https://doi.org/10.3390/molecules200917244 - 18 Sep 2015

Cited by 65 | Viewed by 9294

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)

534 KiB

Open AccessReview

Towards the Development of Functionalized PolypyridineLigands for Ru(II) Complexes as Photosensitizers inDye-Sensitized Solar Cells (DSSCs)

by Adewale O. Adeloye and Peter A. Ajibade

Molecules 2014, 19(8), 12421-12460; https://doi.org/10.3390/molecules190812421 - 15 Aug 2014

Cited by 58 | Viewed by 11695

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 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)

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1534 KiB

Open AccessReview

Ruthenium Complexes as NO Donors for Vascular Relaxation Induction

by Renata Galvão De Lima, Bruno Rodrigues Silva, Roberto Santana Da Silva and Lusiane Maria Bendhack

Molecules 2014, 19(7), 9628-9654; https://doi.org/10.3390/molecules19079628 - 07 Jul 2014

Cited by 34 | Viewed by 10890

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 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)

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596 KiB

Open AccessReview

Experimental and Theoretical Perspectives of the Noyori-Ikariya Asymmetric Transfer Hydrogenation of Imines

by Jiří Václavík, Petr Šot, Jan Pecháček, Beáta Vilhanová, Ondřej Matuška, Marek Kuzma and Petr Kačer

Molecules 2014, 19(6), 6987-7007; https://doi.org/10.3390/molecules19066987 - 28 May 2014

Cited by 17 | Viewed by 8817

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. 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)

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519 KiB

Open AccessReview

Ruthenium Tetroxide and Perruthenate Chemistry. Recent Advances and Related Transformations Mediated by Other Transition Metal Oxo-species

by Vincenzo Piccialli

Molecules 2014, 19(5), 6534-6582; https://doi.org/10.3390/molecules19056534 - 21 May 2014

Cited by 54 | Viewed by 15539

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 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)

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1408 KiB

Open AccessReview

Ruthenium^II Complexes bearing Fused Polycyclic Ligands: From Fundamental Aspects to Potential Applications

by Ludovic Troian-Gautier and Cécile Moucheron

Molecules 2014, 19(4), 5028-5087; https://doi.org/10.3390/molecules19045028 - 22 Apr 2014

Cited by 59 | Viewed by 16539

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 based [...] Read more.

(This article belongs to the Special Issue Ruthenium Complex)

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488 KiB

Open AccessReview

Magnetically Recoverable Ruthenium Catalysts in Organic Synthesis

by Dong Wang and Didier Astruc

Molecules 2014, 19(4), 4635-4653; https://doi.org/10.3390/molecules19044635 - 15 Apr 2014

Cited by 36 | Viewed by 7515

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 focused [...] Read more.

(This article belongs to the Special Issue Ruthenium Complex)

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