Author Archive

Themed Issue: Stimuli responsive materials

We are delighted to present the Chem Soc Rev themed issue on stimuli responsive materials.

Guest editors Patrick Theato, Brent Sumerlin, Rachel O’Reilly and Thomas Epps III introduce the issue in their Editorial.

C3CS90057FMany applications in technology, biology, and society do benefit from materials with increased functionality and adaptability. As a result, according to Theato, Sumerlin, O’Reilly and Epps, materials science has rapidly evolved to meet these demands by enabling the preparation and increased fundamental understanding of responsive materials with adaptable properties and behaviours.

C3CS90067C

Together with our guest editors, we hope this special issue of excellent Review Articles and Tutorial Reviews will serve as a consolidated overview to many of the most important recent advances in the field.

Browse all the reviews from this themed issue online –

Stimuli responsive materials

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Chem Soc Rev reviews in 2013 Cancer Nanotechnology collection– free till 28 July

We are pleased to present a web collection of articles from publications across the RSC journal portfolio demonstrating the use of (nano)technology in the diagnosis, imaging and treatment of cancer.

This web collection will be free to access until the 28th July, so register for an RSC Publishing personal account and read this cutting edge research for free this week!

Read these Chem Soc Rev reviews as part of this special cancer nanotechnology collection:

Cytokines as biomarkers of nanoparticle immunotoxicity
Mahmoud Elsabahy and Karen L. Wooley
Chem. Soc. Rev., 2013,42, 5552-5576
DOI: 10.1039/C3CS60064E

Glyconanotechnology
Niels C. Reichardt, Manuel Martín-Lomas and Soledad Penadés
Chem. Soc. Rev., 2013,42, 4358-4376
DOI: 10.1039/C2CS35427F

Cancer detection using nanoparticle-based sensors
Maëlle Perfézou, Anthony Turner and Arben Merkoçi
Chem. Soc. Rev., 2012,41, 2606-2622
DOI: 10.1039/C1CS15134G

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Huw Davies appointed as Chem Soc Rev Associate Editor

We are very pleased to appoint Professor Huw Davies as a new Associate Editor for Chem Soc Rev.  Huw has been involved with the journal in various capacities since 2004 and will now be handling submissions in the areas of organic chemistry and catalysis.

Huw is the Asa Griggs Candler Professor of Chemistry at Emory University in Atlanta, USA.  Work within the Davies group at Emory draws upon an established knowledge of asymmetric synthesis and catalysis to discover and develop novel methodologies, with the ultimate goal of defining enabling technologies for the chemical community.  In 2007, Huw became a Fellow of the Royal Society of Chemistry.

Chem Soc Rev now has four Associate Editors handling submissions to the journal:

  • David Amabilino (ICMAB) – supramolecular chemistry, macrocycles, self-assembly, chirality  and stereochemistry
  • Huw Davies (Emory University) – organic chemistry and catalysis
  • Douglas Stephan (University of Toronto) – inorganic chemistry
  • Zhong-Qun Tian (Xiamen University) – physical chemistry

Read more about Huw’s research in his recent articles:

Rhodium-catalyzed enantioselective cyclopropanation of electron-deficient alkenes
Hengbin Wang, David M. Guptill, Adrian Varela-Alvarez, Djamaladdin G. Musaev and Huw M. L. Davies
Chem. Sci., 2013, Advance Article
DOI: 10.1039/C3SC50425E, Edge Article

Convenient method for the functionalization of the 4- and 6-positions of the androgen skeleton
Daniel Morton, Allison R. Dick, Debashis Ghosh and Huw M. L. Davies
Chem. Commun., 2012,48, 5838-5840
DOI: 10.1039/C2CC31973J, Communication

Guiding principles for site selective and stereoselective intermolecular C–H functionalization by donor/acceptor rhodium carbenes
Huw M. L. Davies and Daniel Morton
Chem. Soc. Rev., 2011,40, 1857-1869
DOI: 10.1039/C0CS00217H, Tutorial Review
From themed collection C–H Functionalisation in organic synthesis

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New clarity in the mechanism for lithium salt-free Wittig reactions

The Wittig reaction was first reported in 1954 and awarded the Nobel Prize in 1979.  Today, it is widely used for the preparation of alkenes by reaction of a carbonyl compound with a phosphonium ylide.  Despite its age and broad utility, differing mechanisms for the Wittig reaction still feature in the literature and textbooks.

Peter Byrne and Declan Gilheany at University College Dublin have written a substantial review of this transformation, which provides definitive evidence regarding the mechanism of lithium salt-free Wittig reactions of phosphonium ylides.

Phosphonium ylides can be represented in either ylide (1a) or ylene (1b) form and they are classified according to their substitution at the α-carbon.  The P–C­ bond of a phosphonium ylide is heavily polarised towards carbon and so ‘R’ groups that offer a greater degree of conjugative stabilisation increase the overall stabilisation of the ylide. Additionally, the nature of the ‘R’ group influences the selectivity for formation of Z or E alkenes.

The mechanism that features in many undergraduate textbooks involves the attack of the carbonyl carbon by the nucleophilic ylide α-carbon to form a betaine intermediate (7), which undergoes ring closure to form an oxaphosphetane (OPA) (8) and subsequently decomposes to form the product alkene (9) and a phosphine oxide (10) by-product.

Byrne and Gilheany present a body of evidence that disputes this mechanistic pathway and instead supports an irreversible [2 + 2] cycloaddition between the ylide and carbonyl compound to directly form the OPA (8).  The OPA then decomposes in a stereospecific manner, meaning that the stereochemistry of the alkene product is determined by the shape of the transition state for the [2 + 2] cycloaddition, and hence the structure of the OPA.  The E-selectivity commonly observed in the case of semi-stabilised and stabilised ylides is explained by a kinetic preference for the formation of trans-OPA, which decomposes to form the E-alkene.

This clarification of the mechanism for the lithium salt-free Wittig reaction will likely feature in future editions of undergraduate textbooks and will encourage many chemistry lecturers to update their course notes before the start of the new academic year.

For more, read this HOT Chem Soc Rev Review Article in full:

The Modern Interpretation of the Wittig Reaction Mechanism
Peter A. Byrne and Declan G. Gilheany
Chem. Soc. Rev., 2013, Advance Article
DOI: 10.1039/C3CS60105F

Alice Williamson is a guest web-writer for Chem Soc Rev.  She is currently a postdoc for the OSDDMalaria Project in Dr. Matthew H Todd’s group at the University of Sydney.

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Themed Issue: Multivalent scaffolds in glycosciences

We are delighted to present the Chem Soc Rev themed issue on multivalent scaffolds in glycosciences .

Guest editors Olivier Renaudet and René Roy introduce the issue in their Editorial.

C3CS90029K

Multivalent interactions between carbohydrates and proteins are involved in major physiological and pathological processes.  According to Renaudet and Roy, with the recent emergence of glycomics, the development of glycoclusters and glycodendrimers capable of mimicking the multivalent display of the cell surface glycocalix has become a major field of research due to their evident interest as diagnostic and therapeutic tool. C3CS90038JA large variety of scaffolds are now available for the multivalent presentation of carbohydrates.

This themed issue contains an excellent collection of Review Articles and Tutorial Reviews which highlights recent advances focused on the chemistry and applications of such multivalent glycosylated structures.

Browse all the reviews from this themed issue online –

Multivalent scaffolds in glycosciences

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Carbohydrate chemistry themed issue

We are delighted to present Chem Soc Rev‘s themed issue on Carbohydrate chemistry – now available online.

Guest editors Injae Shin and Kwan Soo Kim, both from Yonsei University in Seoul, introduce the issue in their Editorial.

This issue contains an excellent collection of Review Articles and Tutorial Reviews which highlights recent advances in glycochemistry and chemical glycobiology, including:

Review Articles

Chemical approaches to study O-GlcNAcylation
Partha S. Banerjee, Gerald W. Hart and Jin Won Cho
Chem. Soc. Rev., 2013, 42, 4345-4357
DOI: 10.1039/C2CS35412H

Glyconanotechnology
Niels C. Reichardt, Manuel Martín-Lomas and Soledad Penadés
Chem. Soc. Rev., 2013, 42, 4358-4376
DOI: 10.1039/C2CS35427F

The development of synthetic antitumour vaccines from mucin glycopeptide antigens
Nikola Gaidzik, Ulrika Westerlind and Horst Kunz
Chem. Soc. Rev., 2013, 42, 4421-4442
DOI: 10.1039/C3CS35470A

Guest editors-C3CS90030DGlycopolymer probes of signal transduction
Laura L. Kiessling and Joseph C. Grim
Chem. Soc. Rev., 2013, 42, 4476-4491
DOI: 10.1039/C3CS60097A

Tutorial Reviews

Chemical probing of glycans in cells and organisms
Sara H. Rouhanifard, Lars Ulrik Nordstrøm, Tianqing Zheng and Peng Wu
Chem. Soc. Rev., 2013, 42, 4284-4296
DOI: 10.1039/C2CS35416K

Fluoro-C-glycosides and fluoro-carbasugars, hydrolytically stable and synthetically challenging glycomimetics
Eric Leclerc, Xavier Pannecoucke, Mélanie Ethève-Quelquejeu and Matthieu Sollogoub
Chem. Soc. Rev., 2013, 42, 4270-4283
DOI: 10.1039/C2CS35403A

Browse all the reviews from this themed issue online – Carbohydrate chemistry

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Xile Hu wins Chem Soc Rev Emerging Investigator Lectureship 2013

On behalf of the Chem Soc Rev Editorial Board, I am delighted to announce that Professor Xile Hu from the Ecole Polytechnique Fédérale de Lausanne (EPFL), Switzerland, has been chosen as the winner of the 2013 Chem Soc Rev Emerging Investigator Lectureship.

This annual award recognises an emerging scientist who has made a significant contribution to their research field.  The Editorial Board commended Professor Hu’s research in the field of catalysis, particularly his development of catalysts, composed of earth-abundant elements, which are used in sustainable chemical synthesis and for efficient chemical energy storage.  With his research group, he has developed base metal catalysts for organic synthesis, bio-mimetic synthetic compounds for [Fe]-hydrogenase, and non-precious and scalable electrocatalysts for H2 production from water.

On winning the Lectureship, Professor Hu says, “It was a nice surprise for me to learn that I was selected for this award, because I know there are many other equally deserving candidates.  I want to thank the Editorial Board members and the staff of Chem Soc Rev for their interest in my group’s research and their support for my career.  The credit is really due to my co-workers who have exercised tremendous creativity, persistence, and work ethic to push our research endeavors forward.  On their behalf, I am thrilled and honoured to accept this award.”

Professor Hu will present his award lecture at an international conference later in the year– keep an eye on this blog for more details.

You can find out more about Professor Hu’s exciting research by reading his recent articles on Chem Soc Rev, Chemical Science and ChemComm:

Organic molecules as mediators and catalysts for photocatalytic and electrocatalytic CO2 reduction
Yeonji Oh and Xile Hu
Chem. Soc. Rev., 2013, 42, 2253-2261
From themed issue on Solar fuels

Fe, Co, and Ni ions promote the catalytic activity of amorphous molybdenum sulfide films for hydrogen evolution
Daniel Merki, Heron Vrubel, Lorenzo Rovelli, Stéphane Fierro and Xile Hu
Chem. Sci., 2012, 3, 2515-2525

Hydrogen evolution across nano-Schottky junctions at carbon supported MoS2 catalysts in biphasic liquid systems
Peiyu Ge, Micheál D. Scanlon, Pekka Peljo, Xiaojun Bian, Heron Vubrel, Arlene O’Neill, Jonathan N. Coleman, Marco Cantoni, Xile Hu, Kyösti Kontturi, BaoHong Liu and Hubert H. Girault
Chem. Commun., 2012, 48, 6484-6486

Nickel-catalyzed cross coupling of non-activated alkyl halides: a mechanistic perspective
Xile Hu
Chem. Sci., 2011, 2, 1867-1886

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1,8-Naphthalimide Derivatives: Chemistry, Physical Properties and Activity as Anticancer and Fluorescent Imaging Agents

Written by guest web-writer Kevin Murnaghan.

In this Review, which is part of the Alfred Werner Nobel Centenary Issue, chemists from the Gunnlaugsson group at Trinity College Dublin (TCD) describe recent advances in the development and use of 1,8-naphthalimides, primarily as anti-cancer agents. The scope and breadth of the review are impressive. The use of 1,8-naphthalimide derivatives as DNA binders and cytotoxic agents, as well as their mode of action, cellular uptake and cell selectivity are discussed and compared.

The group at TCD, among others, have prepared a large library of 1,8-naphthalimides. A richly diverse group of materials of varying complexity has been realised, enabled by a powerful, yet simple synthetic strategy. Materials designed to modulate the photophysical response of the aromatic unit are described, as are a range of bis-naphthalimides.

General synthetic route and numbering of 1,8-naphthlimide.

Examples of materials reviewed include mono and bis 1,8-naphthalimides derived from polyamines, amino acids, peptides, Tröger’s bases, and norbornanes. Details are given of effective therapeutics with varying naphthalimide substituents, and also with other aromatics or heteroatomics containing similar functionality. A part of the review is devoted to the coordination chemistry of selected derivatives with metal likes gold or platinum. Additionally, the properties of examples bearing organometallic and coordinated metal fragments such as ruthenium tris-bipyridine are discussed.

The absorption, excitation and emission spectra of a 4-aminonaphthalimide derivative in 10 mM phosphate buffer at pH 7.0 (for structure 68)

The naphthilamide group can neatly interact with biomolecules such as DNA via several modes, including intercalation. This combined with favourable photophysical properties ensures that these materials make extremely useful dual function therapeutic and fluorescent imaging agents. Much qualitative and quantitative clinical information is presented. Best performing derivatives are identified and described in various stage clinical trials against selected cell lines and clinical models.

This broad, highly informative and concise Review should prove to be of interest to a wide range of scientists from pure and multi disciplinary fields. A vast amount of information is given and is well referenced, dealing with the physical, chemical, supramolecular and favourable therapeutic properties of 1,8-napthalimide derivatives.

Read this Chemical Society Reviews article today:

Recent advances in the development of 1,8-naphthalimide based DNA targeting binders, anticancer and fluorescent cellular imaging agents

Swagata Banerjee, Emma B. Veale, Caroline M. Phelan, Samantha A. Murphy, Gillian M. Tocci, Lisa J. Gillespie, Daniel O. Frimannsson, John M. Kelly and Thorfinnur Gunnlaugsson
Chem. Soc. Rev., 2013, 42, 1601-1618
DOI: 10.1039/C2CS35467E

Kevin Murnaghan is a guest web-writer for Chemical Society Reviews.  He is currently a Research Chemist in the Adhesive Technologies Business Sector of Henkel AG & Co. KGaA, based in Düsseldorf, Germany. His research interests focus primarily on enabling chemistries and technologies for next generation adhesives and surface treatments.  (Any views expressed here are his personal ones and not those of Henkel AG & Co. KGaA.)

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Designing a new antifungal glycoconjugate vaccine

Potential conjugate vaccines against Candida albicans, a common pathogen which in its most virulent form may cause life-threatening bloodstream infections such as bacterial meningitis in infants and immunocompromised adults, are currently being developed.

As part of the upcoming Chem Soc Rev carbohydrate chemistry themed issue, this review article by members of the Bundle Research Group from the Alberta Glycomics Centre at the University of Alberta highlights the latest and most significant prospects for candidate vaccines against C. albicans. It also contextualises their work on conjugate vaccine design and evaluation within current knowledge on antibody-carbohydrate interactions and glycoconjugate vaccines development.

Their experimental findings show that conjugate vaccines containing disaccharide or trisaccharide attached to immunogenic proteins reduced fungal burden.

graphical abstract

Related PowerPoint slides on “β1,2-Mannans Conformationally Interesting Molecules” are also available as electronic supplementary information (ESI) – take a look at these for free.

Read this Chemical Society Reviews article today:

Designing a new antifungal glycoconjugate vaccine
Margaret A. Johnson and David R. Bundle
Chem. Soc. Rev., 2013, Advance Article
DOI: 10.1039/C2CS35382B

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