NJC Blog

Selective sensing of phosphates derivatives, including nucleotides and inorganic phosphates, is high on the targets list due to their pivotal role in biological systems. In this NJC paper, Kumaresh Ghosh et al. (University of Kalyani, India) have designed a simple pincer-like receptor that selectively recognises tetra- butylammonium dihydrogenphosphate in CH3CN over a series of other anions by exhibiting characteristic excimer emission in fluorescence. Also the simple receptor 1 fluoro- metrically distinguishes ATP from ADP and AMP in aqueous CH3CN.

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A new ortho-phenylenediamine-based cleft for selective sensing of H2PO4− and ATP, Kumaresh Ghosh and Indrajit Saha
New J. Chem., 2011, Advance Article
DOI: 10.1039/C1NJ20116F

Continuing on their pioneering studies, the Roses and co-workers show in this NJC Letter how phosphino and thienyl substituents are incorporated to (cyclohexadienyl)Mn(CO)3 systems, ultimately forming arenes or chiral cyclohexenones.
‘The new eta-5 complexes are particularly attractive, knowing that planar chiral ligands based on tricarbonyl-metal complexes are beginning to play important roles in enantioselective catalysis, with a “spectator” metal distinct from the catalytically active metal’, says Francoise Rose-Munch

So far, most of the previous examples relied on a planar chiral (η6-arene)Cr(CO)3 scaffold and more scarcely on (η5-Cp)Mn(CO)3. The latter compounds containing a cyclopentadienyl platform are the only tricarbonylmanganese complexes used as catalysts and up to now, complexes such as (η5-cyclohexadienyl)Mn(CO)3 had never been employed for the design of planar chiral ligands.

This NJC letter has been selected as a ‘Hot’, and will be of interest to organometallic chemists and the synthetic organic community alike, in the search of new routes to chiral systems.

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• This article will be included in the NJC special issue in the Honour of Didier Astruc, on the occasion of his 65th birthday – Coming soon.

Phosphino-substituted (η5-cyclohexadienyl)tricarbonylmanganese complexes: synthesis and structure
Françoise Rose-Munch, Derya Cetiner, Murielle Chavarot-Kerlidou and Eric Rose
New J. Chem., 2011, Advance Article
DOI: 10.1039/C1NJ20152B, Letter

Crooks and co-workers (University of Texas, USA) report the synthesis and characterization of Pt and Pd dendrimer-encapsulated nanoparticles (DENs) using the method of galvanic exchange. In the presence of either PtCl₄²⁻ or PdCl₄²⁻, the less noble Cu DENs oxidize to Cu²⁺ leaving behind an equal-sized DEN of Pt or Pd, respectively. This methodology is shown to be much faster and giving higher yields than using the common synthetic route i.e. direct reduction with BH₄⁻.Equally important, the detailed characterization presented demonstrates that the structure and composition of Pt and Pd DENs synthesized by direct BH₄⁻ reduction and galvanic exchange are indistinguishable.



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Synthesis, characterization, and electrocatalysis using Pt and Pd dendrimer-encapsulated nanoparticles prepared by galvanic exchange
Surojit Pande, Michael G. Weir, Brian A. Zaccheo and Richard M. Crooks
New J. Chem., 2011, Advance Article DOI: 10.1039/C1NJ20083F, Paper.

Scientists from the Universities of Rennes and Nancy in France have developed dual-role biphotonic chromophores for photodynamic therapy (PDT) applications that retain fluorescence properties, thus enabling their 3-D localization and the selective irradiation of cancer cells when combined with targeting.

In their paper selected as ‘Hot Article’, the collaboration led by Mireille Blanchard-Desce presents the synthesis and photophysical study of “banana-shaped” chromophores where the nature of the conjugated backbone is modified by playing with the aromatic units (a complementary approach to that based on the incorporation of heavy atom substituents).

By optimizing the chromophore structure of a series of fluorene derivatives, the researchers were able to design photosensitizers exhibiting large two-photon adsorption (TPA) cross section in the biologically useful spectral region combined with singlet oxygen production.

‘This route allows to combine in a single biphotonic chromophore several features highly desirable for two-photon PDT: fluorescence (for localisation and subsequent localized irradiation), large and broad TPA responses in the spectral range of interest for bio-oriented applications (700-1000 nm), as well reasonable singlet oxygen sensitization ability’, says Mireille Blanchard-Desce.

The team is now working on developing nano-objects with very high TPA, that incorporate the biphotonic sensitizers.

Banana-shaped biphotonic quadrupolar chromophores: from fluorophores to biphotonic photosensitizers
Cédric Rouxel, Marina Charlot, Youssef Mir, Céline Frochot, Olivier Mongin and Mireille Blanchard-Desce
New J. Chem., 2011, Advance Article
DOI: 10.1039/C1NJ20073A, Paper

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In this NJC Hot Article, Richard Compton and co-workers at the University of Oxford highlight novel electro-synthetic applications of ionic liquids.

The team has decorated carbon nanotubes with Palladium nanoparticles and used the composite material for the efficient electrochemical deprotection of common functional groups in ionic liquids (IL), thus demonstrating that Pd nanoparticles can be used for clean, efficient, safe electro- chemical hydrogenolysis in IL media.

This NJC article will be of interest to synthetic organic and inorganic chemists, electrochemists, material chemists, pharmaceutical chemists and process chemists alike.

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Palladium nanoparticle-modified carbon nanotubes for electrochemical hydrogenolysis in ionic liquids
Yao Meng, Leigh Aldous, Ben S. Pilgrim, Timothy J. Donohoe and Richard G. Compton
New J. Chem., 2011, Advance Article
DOI: 10.1039/C1NJ20070D, Paper

Ferrocene units confer a set of interesting properties to ligands for transition metal complexes, such as reversible redox- properties, planar chirality, or strong electron donating ability. While there are numerous examples of ferrocenylphosphines in which the ferrocene unit is directly bonded to the active coordination center – therefore maximizing its impact – attempts at stabilizing a carbene center using one or two ferrocenyl substituents had yet to prove successful.

Now, Guy Bertrand and colleagues at the University of California, Riverside, have successfully prepared the first stable carbene featuring a ferrocenyl unit directly bonded to the electron-deficient center, by using a pi-electron-donating substituent in the form of an amino group. The team was able to spectroscopically characterize and chemically trap the novel (amino)(ferrocenyl)carbene compound.

Such work is envisioned to open perspectives for the synthesis of new types of carbene ligands, and will be of high relevance to researchers in fundamental chemistry, organometallics, supramolecular chemistry, catalysis and beyond. Challenges ahead now include the further stabilization of such carbenes, via the preparation of cyclic ferrocenylaldiminium systems.

A persistent (amino)(ferrocenyl)carbene
Alan DeHope, Daniel Mendoza-Espinosa, Bruno Donnadieu and Guy Bertrand
New J. Chem., 2011, Advance Article
DOI: 10.1039/C1NJ20170K, Paper

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This article will be part of the themed issue of NJC honouring the life and work of Prof. Didier Astruc, on the occasion of his 65th birthday – Coming soon.

A new facet of Phosphole chemistry is being uncovered it this NJC Letter by François Mathey et al. at the Nanyang Technological University, Singapore. Phosphole rings have been known for a long time to dimerize via [4+2] cycloaddition whenever the phosphorus lone pair is oxidized or complexed. The [2+2] dimerization, on the contrary, is almost unknown.

Now, the authors show that a minor change in the structure of the bisphospholes derivative – i.e. P-O-P vs. P-S-P – completely suppresses the familiar (4+2)-cycloaddition in favour of the thermally forbidden (2+2) -cycloaddition despite considerable steric constraint.

Under solar light at room temperature, the tungsten pentacarbonyl complex of the P–S–P-linked biphosphole undergoes a [2+2] intramolecular cycloaddition. Then, this [2+2] dimer gives the original [4+4] dimer via a Cope rearrangement. This sequence stands in sharp contrast with the behavior of the corresponding P–O–P-linked biphosphole which undergoes a classical [4+2] cycloaddition.

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Intramolecular [4+2] versus [2+2] cycloadditions in P–X–P-linked biphospholes (X = O, S)
Matthew P. Duffy, Yuhan Lin, Liow Yu Ting and François Mathey
New J. Chem., 2011, Advance Article
DOI: 10.1039/C1NJ20087A, Letter

This article will be part of the themed issue of NJC honouring the life and work of Prof. Didier Astruc, on the occasion of his 65th birthday – Coming soon.