Chemical Science Blog

Streamlined synthesis yields longer sugar chains

12 Aug 2015

Emma Cooper writes about a hot Chemical Science article for Chemistry World

By using bigger building blocks, scientists in the UK have shown they can make much longer oligosaccharide sequences than previously possible.

The traditional synthetic route to long chain oligosaccharides is drawn out and complicated; they require numerous steps to produce the precursor tetrasaccharides, then further steps to connect these precursors into long chains. Normally they’re made by an iterative two block process, generating chains up to 12 units long. Now, a four block approach, developed by John Gardiner and colleagues at the University of Manchester, significantly reduces the number of steps enabling longer sugar lengths from 16 up to 40 units. Read the full article in Chemistry World»

Read the original journal article in Chemical Science – it’s open access:
Making the longest sugars: a chemical synthesis of heparin-related [4]n oligosaccharides from 16-mer to 40-mer
Steen U. Hansen, Gavin J. Miller, Matthew J. Cliff, Gordon C. Jayson and John M. Gardiner
Chem. Sci., 2015, Advance Article
DOI: 10.1039/C5SC02091C, Edge Article

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Top 25 Chemical Science articles April–June 2015

04 Aug 2015

By Bethany Johnson.

The 25 most-downloaded Chemical Science articles in the second quarter of 2015 were as follows:

Copper-catalyzed intermolecular C(sp³)–H bond functionalization towards the synthesis of tertiary carbamates
Prasanna Kumara Chikkade, Yoichiro Kuninobu and Motomu Kanai
DOI: 10.1039/C5SC00238A, Edge Article

Palladium(0) NHC complexes: a new avenue to highly efficient phosphorescence
Adam F. Henwood, Mathieu Lesieur, Ashu K. Bansal, Vincent Lemaur, David Beljonne, David G. Thompson, Duncan Graham, Alexandra M. Z. Slawin, Ifor D. W. Samuel, Catherine S. J. Cazin and Eli Zysman-Colman
DOI: 10.1039/C4SC03914A, Edge Article

Rh-catalyzed decarbonylation of conjugated ynones via carbon–alkyne bond activation: reaction scope and mechanistic exploration via DFT calculations
Alpay Dermenci, Rachel E. Whittaker, Yang Gao, Faben A. Cruz, Zhi-Xiang Yu and Guangbin Dong
DOI: 10.1039/C5SC00584A, Edge Article

Sulfonyl fluorides as privileged warheads in chemical biology
Arjun Narayanan and Lyn H. Jones
DOI: 10.1039/C5SC00408J, Perspective

Computational discovery and experimental verification of tyrosine kinase inhibitor pazopanib for the reversal of memory and cognitive deficits in rat model neurodegeneration
Yongliang Yang, Guohui Li, Dongyu Zhao, Haoyang Yu, Xiliang Zheng, Xiangda Peng, Xiaoe Zhang, Ting Fu, Xiaoqing Hu, Mingshan Niu, Xuefei Ji, Libo Zou and Jin Wang
DOI: 10.1039/C4SC03416C, Edge Article

A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors
Bo He, Jing Dai, Danylo Zherebetskyy, Teresa L. Chen, Benjamin A. Zhang, Simon J. Teat, Qichun Zhang, Linwang Wang and Yi Liu
DOI: 10.1039/C5SC00304K, Edge Article

Spatial imaging of carbon reactivity centers in Pd/C catalytic systems
E. O. Pentsak, A. S. Kashin, M. V. Polynski, K. O. Kvashnina, P. Glatzel and V. P. Ananikov
DOI: 10.1039/C5SC00802F, Edge Article

Chemical assay-guided natural product isolation via solid-supported chemodosimetric fluorescent probe
Hongjun Jeon, Chaemin Lim, Ji Min Lee and Sanghee Kim
DOI: 10.1039/C5SC00360A, Edge Article

Very bright mechanoluminescence and remarkable mechanochromism using a tetraphenylethene derivative with aggregation-induced emission
Bingjia Xu, Jiajun He, Yingxiao Mu, Qiangzhong Zhu, Sikai Wu, Yifan Wang, Yi Zhang, Chongjun Jin, Changcheng Lo, Zhenguo Chi, Alan Lien, Siwei Liu and Jiarui Xu
DOI: 10.1039/C5SC00466G, Edge Article

Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry
Swati S. Nigudkar and Alexei V. Demchenko
DOI: 10.1039/C5SC00280J, Perspective

Combination of Ru(II) complexes and light: new frontiers in cancer therapy
Cristina Mari, Vanessa Pierroz, Stefano Ferrari and Gilles Gasser
DOI: 10.1039/C4SC03759F, Perspective

Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations
Alan R. Burns, Amaël G. E. Madec, Darryl W. Low, Iain D. Roy and Hon Wai Lam
DOI: 10.1039/C5SC00753D, Edge Article

Ratiometric detection of pH fluctuation in mitochondria with a new fluorescein/cyanine hybrid sensor
Yuncong Chen, Chengcheng Zhu, Jiajie Cen, Yang Bai, Weijiang He and Zijian Guo
DOI: 10.1039/C4SC04021J, Edge Article

Enantioselective and diastereoselective azo-coupling/iminium-cyclizations: a unified strategy for the total syntheses of (−)-psychotriasine and (+)-pestalazine B
Qi Li, Tingting Xia, Licheng Yao, Haiteng Deng and Xuebin Liao
DOI: 10.1039/C5SC00338E, Edge Article

Iron(II)-catalyzed asymmetric intramolecular olefin aminochlorination using chloride ion
Cheng-Liang Zhu, Jun-Shan Tian, Zhen-Yuan Gu, Guo-Wen Xing and Hao Xu
DOI: 10.1039/C5SC00221D, Edge Article

Reversible photo-induced trap formation in mixed-halide hybrid perovskites for photovoltaics
Eric T. Hoke, Daniel J. Slotcavage, Emma R. Dohner, Andrea R. Bowring, Hemamala I. Karunadasa and Michael D. McGehee
DOI: 10.1039/C4SC03141E, Edge Article

Evaluating metal–organic frameworks for natural gas storage
Jarad A. Mason, Mike Veenstra and Jeffrey R. Long
DOI: 10.1039/C3SC52633J, Perspective

Enhancing H₂ evolution performance of an immobilised cobalt catalyst by rational ligand design
Janina Willkomm, Nicoleta M. Muresan and Erwin Reisner
DOI: 10.1039/C4SC03946G, Edge Article

Dialkylbiaryl phosphines in Pd-catalyzed amination: a user’s guide
David S. Surry and Stephen L. Buchwald
DOI: 10.1039/C0SC00331J, Perspective

Diverse reactivity of a tricoordinate organoboron L₂PhB: (L = oxazol-2-ylidene) towards alkali metal, group 9 metal, and coinage metal precursors
Lingbing Kong, Rakesh Ganguly, Yongxin Li and Rei Kinjo
DOI: 10.1039/C5SC00404G, Edge Article

Is a polymer semiconductor having a “perfect” regular structure desirable for organic thin film transistors?
Wei Hong, Shaoyun Chen, Bin Sun, Mark A. Arnould, Yuezhong Meng and Yuning Li
DOI: 10.1039/C5SC00843C, Edge Article

Palladium-catalyzed cross-coupling of α-bromocarbonyls and allylic alcohols for the synthesis of α-aryl dicarbonyl compounds
Yang Yu and Uttam K. Tambar
DOI: 10.1039/C5SC00505A, Edge Article

Charging and discharging at the nanoscale: Fermi level equilibration of metallic nanoparticles
Micheál D. Scanlon, Pekka Peljo, Manuel A. Méndez, Evgeny Smirnov and Hubert H. Girault
DOI: 10.1039/C5SC00461F, Perspective

A highly selective ratiometric near-infrared fluorescent cyanine sensor for cysteine with remarkable shift and its application in bioimaging
Zhiqian Guo, SeongWon Nam, Sungsu Park and Juyoung Yoon
DOI: 10.1039/C2SC20540H, Edge Article

Virtual screening for high affinity guests for synthetic supramolecular receptors
William Cullen, Simon Turega, Christopher A. Hunter and Michael D. Ward
DOI: 10.1039/C5SC00534E, Edge Article

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Join us in Brazil for Challenges in Chemical Renewable Energy

03 Aug 2015

By Heather Montgomery, Deputy Editor.

Don’t miss out on great student rates: $80 for Royal Society of Chemistry/Brazilian Chemical Society members and $90 for non-members.

It is just a few weeks until the International Symposia on Advancing the Chemical Sciences (ISACS) symposia take the series to Brazil for the first time.

Register by 1 September, 2015 to secure your place

We will have a lively programme discussing the current Challenges in Chemical Renewable Energy with researchers from across the globe, incuding:

James Durrant (Imperial College London, UK)

Eduardo Falabella (Federal University of Rio de Janeiro and PETROBRAS, Brazil)

Marc Fontecave (Collège de France, France)

Hubert Girault (Federal Polytechnic School of Lausanne, Switzerland)

Ernesto R. Gonzalez (University of São Paulo, Brazil)

Daniel Nocera (Harvard University, USA)

Erwin Reisner (University of Cambridge, UK)

Keith Waldron (Institute of Food Research, UK)

Karen Wilson (Aston University, UK)

Check out the full provisional programme on our website.

*Students, take advantage of a generous discount: $80 for Royal Society of Chemistry/Brazilian Chemical Society members and $90 for non-members!*

Our hope is that delegates will be exposed to new areas of research, encouraging the cross fertilization of ideas. We look forward to seeing you in Brazil!

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Boroles get a stability boost

28 Jul 2015

By Bethany Johnson.

Anisha Ratan writes about a hot Chemical Science article for Chemistry World

Scientists from Germany have reported a breakthrough in borole stability, using bulky fluoromesityl groups, which could help these anti-aromatic molecules realise their potential in optoelectronic devices.

Boroles are heterocycles with a 4π-electron BC4 ring and subsequent electron-accepting abilities. This makes them great candidates for electron-transporting and accepting materials in organic light-emitting diodes and photovoltaics. Read the full article in Chemistry World»

Read the original journal article in Chemical Science – it’s open access:
Taming the beast: fluoromesityl groups induce a dramatic stability enhancement in boroles
Zuolun Zhang, Robert M. Edkins, Martin Haehnel, Marius Wehner, Antonius Eichhorn, Lisa Mailänder, Michael Meier, Johannes Brand, Franziska Brede, Klaus Müller-Buschbaum, Holger Braunschweig and Todd B. Marder
Chem. Sci., 2015, Advance Article, DOI: 10.1039/C5SC02205C, Edge Article

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Photoredox catalysis mechanisms seen in new light

24 Jul 2015

By Bethany Johnson.

Richard Massey writes about a hot Chemical Science article for Chemistry World

A debate over whether photoredox-catalysed reactions proceed via chain processes may now be settled, thanks to new mechanistic insight brought to light by scientists in the US. The research, led by Tehshik Yoon at the University of Wisconsin–Madison, shows that commonly used light/dark experiments can result in mechanistic misdiagnosis.

Whilst interest in photoredox catalysis has recently burgeoned – the reactions are used in natural product and pharmaceutical synthesis – our understanding of their mechanisms hasn’t kept pace. In particular, the extent to which the reactions involve chain processes is not fully understood, leading to conflicting explanations. Several groups have reported that the final product-generating step proceeds only by reduction of the radical cation product by the reduced photocatalyst in a closed catalytic cycle, whilst others have reported that the product is formed by an additional chain propagation step involving another equivalent of substrate. Read the full article in Chemistry World»

Read the original journal article in Chemical Science – it’s open access:
Characterizing chain processes in visible light photoredox catalysis
Megan A. Cismesia and Tehshik P. Yoon
Chem. Sci., 2015, Advance Article, DOI: 10.1039/C5SC02185E, Edge Article

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Hot Chemical Science articles for July

13 Jul 2015

By Bethany Johnson.

Here are some recent referee-recommended Chemical Science articles for you to enjoy – all are open access and free to download:

Theoretical studies on a carbonaceous molecular bearing: association thermodynamics and dual-mode rolling dynamics
Hiroyuki Isobe, Kosuke Nakamura, Shunpei Hitosugi, Sota Sato, Hiroaki Tokoyama, Hideo Yamakado, Koichi Ohno and Hirohiko Kono
DOI: 10.1039/C5SC00335K, Edge Article

C5SC00335K GA

Molecular understandings on the activation of light hydrocarbons over heterogeneous catalysts
Zhi-Jian Zhao, Cheng-chau Chiu and Jinlong Gong
DOI: 10.1039/C5SC01227A, Perspective

C5SC01227A GA

Selective glycoprotein detection through covalent templating and allosteric click-imprinting
Alexander Stephenson-Brown, Aaron L. Acton, Jon A. Preece, John S. Fossey and Paula M. Mendes
DOI: 10.1039/C5SC02031J, Edge Article

C5SC02031J GA

Biomimetic versus enzymatic high-potential electrocatalytic reduction of hydrogen peroxide on a functionalized carbon nanotube electrode
Bertrand Reuillard, Solène Gentil, Marie Carrière, Alan Le Goff and Serge Cosnier
DOI: 10.1039/C5SC01473E, Edge Article

C5SC01473E GA

Small molecular logic systems can draw the outlines of objects via edge visualization
Jue Ling, Gaowa Naren, Jessica Kelly, David B. Fox and A. Prasanna de Silva
DOI: 10.1039/C5SC01537E, Edge Article

C5SC01537E GA

Imaging metals in biology: balancing sensitivity, selectivity and spatial resolution
Dominic J. Hare, Elizabeth J. New, Martin D. de Jonge and Gawain McColl
DOI: 10.1039/C5CS00055F, Tutorial Review

C5CS00055F GA

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Smaller, better chemosensing porous polymers

10 Jul 2015

By Anthea Blackburn, Web Science Writer.

Researchers from the CSIR–National Chemical Laboratory have demonstrated that upon exfoliation of an imide-based covalent organic framework to its nanosheet counterpart, its ability to detect the presence of nitroaromatices is dramatically enhanced.

The exploitation of porous frameworks, both metal-organic and wholly organic in nature, for their ability to take up and store gases and small molecules, has been well reported over the past few decades. The modularity of these frameworks with respect to their size, flexibility and chemical functionality gives rise to their propensity to adsorb a myriad of chemicals; however, this process is not always selective and the chemical instability of these frameworks can cause difficulties in their extension towards real-life applications. A framework that a) is able to favourably and preferentially adsorb chemicals with high sensitivity, and b) exhibits chemical stability under a wide range of conditions, remains somewhat elusive and is thus a hot topic of investigation in many research groups.

Whilst the uptake and sensing properties of two-dimensional porous polymers have been well studied, the bulk nature of these materials often results in the decrease of their properties on account of the extensive aggregation of the polymer layers and resulting reduction of electrons available to interact with guest molecules. Rahul Banerjee and researchers from the Council of Scientific and Industrial Research – National Chemical Laboratory set out to address this limitation in the field of porous polymers through the Liquid Phase Exfoliation of an imide-based covalent organic framework to its covalent organic nanosheet (CON) analogue. Such a CON, which contains between five and fifteen layers of the material, has chemical and thermal stability equal to that of its bulk counterpart; however, its sensing ability down to 10^–5 M towards 2,4,6-trinitrophenol (TNP) and other nitroaromatic explosive chemicals is far superior. Furthermore, this reversible detection upon uptake can be seen both spectroscopically in solution and visually in the solid state via the turning off and on of the CON luminescence respectively.

The ability to quickly and selectively detect chemicals is of paramount interest to researchers worldwide, particularly those chemicals that pose a threat to societal health and safety. The methodology involving covalent organic nanosheets developed in this research offers a new approach to and a first step towards increasing the selectivity and sensitivity of detection by porous frameworks for chemicals, in this case nitroaromatics like TNT.

Read this HOT ChemSci article in full – it’s open access and free to download:

Chemical sensing in two dimensional porous covalent organic nanosheets
Gobinda Das, Bishnu P. Biswal, Sharath Kandambeth, V. Venkatesh, Gagandeep Kaur, Matthew Addicoat, Thomas Heine, Sandeep Verma and Rahul Banerjee
Chem. Sci., 2015, 6, 3931–3939.
DOI: 10.1039/C5SC00512D, Edge Article

About the Writer

Anthea Blackburn is a guest web writer for Chemical Science. Anthea is a recent graduate student hailing from New Zealand, who studied at Northwestern University in the US under the tutelage of Prof. Fraser Stoddart (a Scot), where she exploited supramolecular chemistry to develop multidimensional systems and study the emergent properties that arise in these superstructures. When time and money allow, she is ambitiously attempting to visit all 50 US states.

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Vy Dong’s organic love story

08 Jul 2015

By Bethany Johnson.

Chemical Science Associate editor Vy Dong recently gave a TEDx talk at UC Irvine. Check out her inspirational 15 minute lecture on YouTube: in it she tells how her family came to the US from Vietnam and why she chose a career in organic chemistry. She also compares organic chemistry to her favourite childhood toy, Lego, and talks about why she describes her students as ‘molecular architects’!

Submit your next high-quality manuscript to Vy Dong’s Chemical Science editorial office

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Insights on a high performing MOF

06 Jul 2015

By Bethany Johnson.

Victoria Richards highlights a recent Chemical Science Perspective article looking at HKUST-1

Metal-organic frameworks (MOFs) have received over a decade’s worth of attention from scientists worldwide. These porous materials can be constructed from almost an infinite combination of organic ligands and metal ions, which has spurred scientists to become creative in their designs, delivering materials with a wide range of useful applications.

In this recently published Chemical Science Perspective, Christopher Hendon and Aron Walsh (recently announced as the winner of the 2015 Chemical Society Reviews Emerging Investigator Lectureship) provide unique insight on the importance of the electronic, magnetic and physical properties of MOFs, focusing their attention on the body of evidence available on HKUST-1.

Many of the most successful MOFs contain arrays of copper paddle wheel motifs, and HKUST-1 is no exception. First reported by Williams in 1999¹, HKUST-1 remains one of the most high-performing materials of its kind and, thanks to it being high in demand, is one of few commercially available MOFs on the market.

With fresh analysis in hand, this report provides researchers with key design principles for the construction of MOFs with tailored chemical and electronic properties, potentially furthering the high-performance applications of these materials.

Read Walsh and Hendon’s Perspective in Chemical Science – it’s open access, and free to download:
Chemical principles underpinning the performance of the metal–organic framework HKUST-1
Christopher H. Hendon and Aron Walsh
Chem. Sci., 2015, Advance Article
DOI: 10.1039/C5SC01489A, Perspective

¹S. S. Chui, S. M. Lo, J. P. H. Charmant, A. G. Orpen and I. D. Williams, Science, 1999, 283, 1148

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Chemical Science Blog

Streamlined synthesis yields longer sugar chains

Join us in Brazil for Challenges in Chemical Renewable Energy

More hot Chemical Science articles for July

Boroles get a stability boost

Photoredox catalysis mechanisms seen in new light

Hot Chemical Science articles for July

Smaller, better chemosensing porous polymers

Vy Dong’s organic love story

Insights on a high performing MOF

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