Chemical Communications: Editor’s Choice

Be sure to read our latest Editor’s Choice article as chosen by Associate Editor Jean-Louis Reymond!

This article is free-to-access until 8th November and can be found alongside our previously chosen articles in our online Editor’s Choice web-collection!

Heptylmannose-functionalized cellulose for the binding and specific detection of pathogenic E. coli” by Jean-Louis Reymond:

In their communication “Heptylmannose-functionalized cellulose for the binding and specific detection of pathogenic E. coli” Madeleine Cauwel et al. exploited the well-known FimH lectin system to devise a selective detection system for adherent-invasive E. coli (AIEC) involved in the pathogenesis of Crohn’s disease (CD). FimH is well known to bind mannosyl glycosides and to occur in AIEC. The trick here was to prepare a modified cellulose (as nanofiber or paper) using click chemistry, profile its lectin binding with state-of-the art chip analysis, verify its ability to block binding of AIEC from a CD patient to intestinal epithelial cells and to decrease AIEC levels in gut microbiota in a murine model, and finally to show that the modified paper binds selectively to pathogenic AIEC but not to benign E. coli.

Simple but effective chemistry, thorough experiments with relevant samples, impressive results. Chemical biology at its best.

 

 

Find our full Editor’s Choice collection online!

Keep up-to-date with our latest journal news on Twitter @ChemCommun or via our blog!

Learn more about ChemComm online! Submit your latest high impact research here!

 

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ChemComm Emerging Investigator Lectureship – nominations now open!

Know an outstanding emerging scientist who deserves recognition? Nominate now for the 2020 ChemComm Emerging Investigator Lectureship

We are pleased to welcome nominations for the 2020 Emerging Investigator Lectureship for ChemComm.

All nominations must be received by Friday 29th November 2019.

ChemComm Emerging Investigator LectureshipChemComm Banner
• Recognises emerging scientists in the early stages of their independent academic career.
• Eligible nominees should have completed their PhD in 2012 or later.
Appropriate consideration will be given to those who have taken a career break or followed a different study path.

Lectureship details
• The recipient of the lectureship will be invited to present a lecture at three different locations over a 12-month period, with at least one of these events taking place at an international conference.
• The recipient will receive a contribution of £1500 towards travel and accommodation costs for their lectures, as well as a certificate.
• The recipient will be asked to contribute a review article for the journal.

How to nominate
Self-nomination is not permitted. Nominators must send the following to the editorial team via 
chemcomm-rsc@rsc.org by Friday 29th November 2019.
• Recommendation letter, including the name, contact details and website URL of the nominee.
• A one-page CV for the nominee, including a summary of their education, dates of key career achievements, a list of up to five of their top independent publications, total numbers of publications and patents, and other indicators of esteem, together with evidence of career independence.
• A copy of the candidate’s best publication to date (as judged by the nominator).
• Two supporting letters of recommendation from two independent referees. These should not be someone from the same institution or the candidate’s post doc or PhD supervisor.

The nominator and independent referees should comment on the candidate’s presenting skills.

Incomplete nominations or those not adhering to the above requirements will not be considered, and nominees will not be contacted regarding any missing or incorrect documents.

Selection procedure
• The editorial team will screen each nomination for eligibility and draw up a shortlist of candidates based on the nomination documents provided.
• The recipient of the lectureship will then be selected and endorsed by a selection panel composed of members of the ChemComm Editorial Board. The winner will be announced in the first half of 2020.

NB: Please note that members of the selection panel from the ChemComm Editorial Board are not eligible to nominate, or provide references, for this lectureship.

For any queries, please contact the editorial team at chemcomm-rsc@rsc.org.

 

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Chemical Communications: Editor’s Choice

Be sure to read our Editor’s Choice articles as chosen by Associate Editors Prof. Penny Brothers & Prof. Manfred Scheer!

Both articles are free-to-access until 4th October and can be found alongside our previously chosen articles in our online Editor’s Choice web-collection!

 

NO sorption, in-crystal nitrite and nitrate production with arylamine oxidation in gas–solid single crystal to single crystal reactions” by et al., as chosen by Penny Brothers:

This year marks 100 years since Alfred Werner’s death in 1919, and it is over a century since he won the 2013 Nobel prize for developing the conceptual framework that we now understand as coordination chemistry. Studies on cobalt complexes formed the cornerstone of Werner’s work, and this paper shows they are still relevant and important well into the 21st century, although with some surprising twists.  Single crystals of tetranuclear Co(II) and Co(III) complexes chemisorb nitric oxide (NO) which, after exposure to O2 physisorbed from air, is transformed to nitrite, nitrate and an aryl nitro group in remarkable single crystal to single crystal reactions.  The medical and biological significance of NO and the solventless redox chemistry all occurring in the crystalline phase suggest exciting possibilities for its highly selective capture and conversion.

 

 

Imidazolium-benzimidazolates as convenient sources of donor-functionalised normal and abnormal N-heterocyclic carbenes” by et al., as chosen by Manfred Scheer:

Mesomeric betaines are related to N-heterocyclic carbenes because of their interconversion by tautomerisation and therefore can act as “instant carbenes”. The authors established now imidazolium-benzimidazolates as a new and highly versatile “instant carbene” system. Depending on the steric demand of the imidazole N-substituent, normal but also abnormal NHC carbene coordination is observed. Thus, unstable but nevertheless highly interesting species are available starting from stable betainic precursors. Therefore, this paper contributes substantially to the chemistry of normal and abnormal N-heterocyclic carbenes.

 

 

 

Find our full Editor’s Choice collection online!

Keep up-to-date with our latest journal news on Twitter @ChemCommun or via our blog!

Learn more about ChemComm online! Submit your latest high impact research here!

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Mechanical Stress Turns These Dendrimers Blue

We all know what happens when materials take too much mechanical stress – they eventually break.

What if you could easily tell when something like a support was close to its maximum stress, before it undergoes a catastrophic event, just by looking at it? One option is to incorporate a mechanochromic polymer, a polymer that changes color when under sufficient mechanical stress, to provide a visual indicator that a material has reached a specific stress threshold. The polymers don’t need to be entirely composed of mechanochromically active moieties to exhibit useful properties; many studies have focused on a single active mechanophore at the center of a large polymer chain. In fact, the mechanical force is greatest at the center of a chain and is directly proportional to the length of the chains. This holds for polymers in solution but hasn’t been extensively studied in the types of bulk systems useful for applications.

Recently, researchers in Japan set out to characterize the effects of chain length and branching on mechanochromic dendrimers, polymers with monodisperse and regularly branched globular structures. Showing that dendrimers exhibit mechanochromism is already a novel result, but their well-defined nature allowed the researchers to draw correlations between structure and bulk responsiveness. They employed diarylbibenzylfuranone (DABBF) as the mechanochromic moiety since it generates arylbenzofuranone (ABF) radicals, which are blue, air-stable, and electron paramagnetic resonance spectroscopy (EPR) active, when exposed to mechanical force (Figure 1).

Figure 1. Structure of the DABBF moiety and the active ABF radicals generated by its dissociation.

These characteristics allow for straightforward qualitative and quantitative analysis. The team coupled the DABBF moiety with two series of dendrimers, with increasing generations having larger and more highly branched monomer units, to create a range of molecular weights and degrees of branching for study. The dendrimers showed a color change from white to blue (Figure 2) when ground in a ball mill, which was used to ensure the reproducibility of the force applied to all samples.

Figure 2. Photographs of the first (top) and second (bottom) mechanochromic dendrimers before and after grinding, showing the color change associated with the generation of ABF radicals.

EPR measurements confirmed the presence of the ABF radicals in the samples after milling, demonstrating that the color change is due to the cleavage of the DABBF. The integrated EPR spectra were used to quantitatively determine the percentage of DABBF moieties that dissociated. The responsiveness of the dendrimers increased exponentially with increasing generation and branching. However, the primary factor governing ABF generation was found to be molecular weight. Two dendrimers with different levels of chain entanglement, but similar molecular weights, exhibited comparable cleavage ratios.  The question then became does molecular weight increase the transfer efficiency of force to the DABBF or does the increased steric bulk make it harder for the ABF radicals to recombine? To probe the kinetics of this process, the researchers varied the grinding time and saw that within 5 minutes all the highly branched samples reached their maximum dissociation level. Additionally, monitoring the ABF recombination showed that even after 6 hours approximately 95% of the radicals remained dissociated in all 3rd and 4th generation dendrimers. These data suggest that the enhancement in responsiveness can be attributed to better force transmission to the DABBF.

This work shows mechanoresponsiveness in a range of dendrimers with varying degrees of branching and rigidity. Not only did they demonstrate novel activity, but the researchers also probed the mechanism of the enhanced activity with increasing molecular weight. This initial study opens avenues to explore polymer rigidity, surface functionality, and other dendrimer features to design new, functional materials.

To find out more, please read:

Mechanochromic dendrimers: the relationship between primary structure and mechanochromic properties in the bulk

Takuma Watabe, Kuniaki Ishizuki, Daisuke Aoki, and Hideyuki Otsuka

Chem. Commun., 2019, 55, 6831-6834.

About the blogger:

Beth Mundy is a PhD candidate in chemistry in the Cossairt lab at the University of Washington in Seattle, Washington. Her research focuses on developing new and better ways to synthesize nanomaterials for energy applications. She is often spotted knitting in seminars or with her nose in a good book. You can find her on Twitter at @BethMundySci.

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Synthesizing Polymers Using CO2

Ring-opening polymerizations produce commercial polymeric materials including epoxy resins, but they usually liberate small molecules such as the greenhouse gas, CO2. In the context of climate change, it is urgent to reduce CO2 emissions. Recently, a group of UK researchers led by Prof. Charlotte K. Williams at the University of Oxford developed a step-growth polymerization method that self-consumed CO2. The work has been published in a recent issue of Chemical Communications.

The synthesis involved two catalytic cycles (Figure 1). The first cycle polymerized L-lactide-O-carboxyanhydride into poly(L-lactide acid) (PLLA) via a ring-opening polymerization and released one CO2 molecule per polymer repeat unit. In the second cycle, epoxide molecules (cyclohexeneoxide) combined with the CO2 generated in the first step and grew into poly(cyclohexene carbonate) (PCHC) from the terminal ends of the PLLA chains. A di-zinc-alkoxide compound catalyzed both cycles and coupled the two processes together. The product is PLLA-b-PCHC block copolymers, which are composed of PLLA and PCHC covalently tethered together.

Figure 1. The two catalytic cycles are joined by a zinc-based catalyst, [LZn2(OAc)2]. The CO2 gas produced in the first step serves as a reactant in the second step. OCA: O-carboxyanhydride; ROP: ring-opening polymerization; CHO: cyclohexeneoxide; ROCOP: ring-opening copolymerization.

The two reactions resulted in block copolymers with few byproducts. In-situ 1H NMR revealed that the reactants in the first step (LLAOCA) were rapidly consumed during the first four hours (Step I, Figure 2a), and the concentration of PLLA increased notably. The concentration of PCHC only markedly increased after the concentration of PLLA saturated (Step II, Figure 2a). The byproduct of the second step, trans-cyclohexene carbonate, exhibited consistently low concentrations. The pronounced single peak in each size-exclusion chromatogram of the corresponding product confirmed the presence of block copolymers, instead of polymer mixtures (Figure 2b). Although the authors did not fully elucidate the origin of the excellent selectivity towards the block copolymer, they speculated that the change in CO2 partial pressure played a role. Significantly, nearly all CO2 molecules were consumed in the second step, with 91% incorporated into the block copolymer, and 9% converted to the byproduct.

Figure 2. (a) The evolution of the concentrations of PLLA, PCHC, and trans-CHC (the byproduct of the second step) with reaction time. (b) Size-exclusion chromatograms of the products at different reaction times. Mn: number-average molecular weight; Đ: polydispersity.

The authors are investigating the detailed polymerization mechanism, as well as identifying new catalysts to expand the polymerization scheme to other polymers.

 

To find out more, please read:

Waste Not, Want Not: CO2 (Re)cycling into Block Copolymers

Sumesh K. Raman, Robert Raja, Polly L. Arnold, Matthew G. Davidson, and Charlotte K. Williams

Chem. Commun., 2019, 55, 7315-7318

 

About the blogger:

Tianyu Liu obtained his Ph.D. (2017) in Chemistry from University of California, Santa Cruz in the United States. He is passionate about scientific communication to introduce cutting-edge research to both the general public and scientists with diverse research expertise. He is a blog writer for Chem. Commun. and Chem. Sci. More information about him can be found at http://liutianyuresearch.weebly.com/.

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Chemical Communications: Editor’s Choice

Featuring exciting research published in ChemComm, hand-picked by our Associate Editors as their favorite recent articles!

Be sure to read our Editor’s Choice articles as chosen by Associate Editors Prof. Jonathan Steed & Prof. Jonathan Sessler!

All articles are free-to-access until 31st August and can be found in our online Editor’s Choice web-collection!

Planar rings in nano-Saturns and related complexes” by Steven M. Bachrach, as chosen by Jonathan Steed:

“This paper lays down the gauntlet to synthetic chemists! The image of a nano-Saturn is immediately eye-catching and scales up molecular host guest chemistry to the multi-nanometre scale. This creative theoretical paper establishes that ortho-nitrogen substitution in aryl macrocycles creates large planar or ribbon structures and then goes on to show that these discs or rings can combine with other nanostructures to construct complexes with interesting shapes. Given the huge interest generated by the mechanically interlocked structures underlying the 2016 Nobel prize in chemistry, these large-scale included systems are real food for thought and I am excited to see if they can be realised experimentally.”

Enhancing selectivity of cation exchange with anion receptors” by 

“These researchers have shown that by using a classic anion binding agent, namely a calix[4]pyrrole, it is possible to modulate the inherent selectivity of liquid-liquid cation extractants. Most current extraction-based separations rely on the use of lipophilic anions as the extractants. These anions, typically the conjugate bases of carboxylic acids, beta-diketones, phosphoric/phosphonic/phosphinic acids, phenols, hydroxyoximes, and sulfonic acids, complex to the cation in question with a selectivity set largely by the local anion-cation coordination environment. However, in this communication the ORNL team has shown that when a calix[4]pyrrole is added to a phenolate-type cation extractant the inherent selectivity is pushed in favor of Cs+ over Na+. This bias in favor of Cs+, which stands in contrast to what would normally be expected, is rationalized in terms of the formation of a highly specific tertiary supramolecular complex involving the calix[4]pyrrole, the anionic phenolate, and the Cs+ cation. Such an organized ternary complex is disfavored in the case of Na+. This work is particularly appealing to me as an Associate Editor for its combination of novelty, insightfulness, and scholarly rigor. It is also attractive to me personally because it demonstrates a new utility for one of my favorite old-but-new molecules, namely calix[4]pyrrole.”

Bonus article: “p-Phosphonic acid calix[8]arene mediated synthesis of ultra-large, ultra-thin, single-crystal gold nanoplatelets” by  et al., as chosen by Jonathan Steed:

“This work reports a very simple system that gives glorious gold nanoplatelets with significant surface area but a thickness of around 6nm. Creating 2D nanocrystals is very challenging and involves highly kinetic conditions. In this case the simple reduction of soluble gold(III) in the presence of a phosphonated acid calix[8]arene macrocycle gives rise to these very well-defined and very unusual morphologies. In this case the role of the calixarene seems to be to attach to the Au(111) surfaces, impeding their growth in one direction and allowing growth in the other to form single-crystal platelets. We are still just scratching the surface of what unusual nanoscale morphologies can do to alter the properties of a material but the present gold nanowafers already show promise as oxygen sensors.”

Find our full Editor’s Choice collection online!

Keep up-to-date with our latest journal news on Twitter @ChemCommun!

Learn more about ChemComm online! Submit your latest high impact research here!

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Raffaella Buonsanti and Corinna Schindler: Winners of the ChemComm Emerging Investigator Lectureship 2019!

On behalf of the ChemComm Editorial Board, we are pleased to announce the winners of the 2019 ChemComm Emerging Investigator Lectureship – Raffaella Buonsanti and Corinna Schindler! Our warmest congratulations to Raffaella and Corinna!

Raffaella Buonsanti

Raffaella Buonsanti obtained her PhD in Nanochemistry in 2010 at the National Nanotechnology Laboratory, University of Salento. Afterwards, she moved to the US where she spent over five years at the Lawrence Berkeley National Laboratory, first as a postdoc and project scientist at the Molecular Foundry and after as a tenure-track staff scientist in the Joint Center for Artificial Photosynthesis.

She is currently a tenure-track Assistant Professor in the Institute of Chemical Sciences and Engineering at EPFL in Switzerland. Her group works at the interface of materials chemistry and catalysis, using colloidal chemistry tools to synthesize controlled and tunable nanocrystals and to advance the current knowledge on the electrocatalytic conversion of small molecules into value-added chemicals. You can also learn more about Raffaella’s group and research on Twitter @lnce_epfl.

 

 

 

Corinna Schindler

Corinna was awarded her PhD in 2010 at the ETH Zurich, where she worked with Professor Erick M. Carreira on the total synthesis of Banyaside B and Microcin SF608. She has been awarded several honors during her independent career, including a 2016 David and Lucile Packard Foundation Fellowship, a 2016 NSF CAREER award, a 2018 Alfred P. Sloan Research Fellowship, a 2018 Camille Dreyfus Teacher-Scholar Award, a 2019 Marion Milligan Mason Award, and a 2019 Presidential Early Career Award for Scientists and Engineers.

She is currently an Assistant Professor at the University of Michigan, Ann Arbor and her group’s research focuses on the development of new synthetic transformations relying on environmentally benign metals and the synthesis of complex molecules of biological importance in cancer treatment and infectious diseases. Find more info about Corinna and her group on Twitter @SchindlerLab.

 

 

 

 

As part of the Lectureship award, Raffaella and Corinna will each present lectures at three locations over the coming year, with at least one of these events taking place at an international conference. Details of the lectures will be announced in due course but keep an eye on Twitter @ChemCommun for details!

Keep up-to-date with our latest journal news on Twitter @ChemCommun or via our blog!

Learn more about ChemComm online! Submit your latest high impact research here!

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Guiding Light with Molecular Crystals

We’re all used to communications and computing happening at high, and seemingly ever-increasing speeds. Continuing on this trajectory requires the development of materials capable of acting as micro/nanoscale waveguides that don’t experience interference effects from strong external electromagnetic fields. Molecular crystals represent an exciting but relatively under-explored materials class due to their inherently limited emission and absorption properties. However, an international group of researchers recently combined two different crystalline materials with complementary optical properties in a filled-hollow crystal architecture, involving no binding materials or polymer matrices.

Figure 1. Spectra and structure of DCA (left) and PDI (right).

The group used 9,10-dicyanoanthracine (DCA) as the hollow outer crystal, with a perylene diimide derivative (PDI) as the interior compound (Figure 1). When combined, these two compounds exhibit fluorescence that covers the visible and near-IR portions of the electromagnetic spectrum. The researchers grew hollow crystals of DCA with diameters ranging from 50-400 μm in diameter with pores of 10-200 μm and filled them with 1-50 μm PDI crystal fibrils manually by hand(!) (Figure 2) (I honestly can’t imagine how many crystals ended up broken during that experimental learning curve!). The assembled structure for study had a single hollow DCA crystal filled with 18 individual PDI fibrils to create the waveguide.

Figure 2. Schematic of hollow crystal architecture (top) with demonstration of construction (bottom).

When the researchers excited the full structure with a 365 nm continuous wavelength LED, both crystal components emitted light that was guided down to the opposite end. The specific makeup of the spectrum depends on the point of illumination; only the excited compounds emit. This supports the active waveguiding capabilities of the materials. The emissive properties can also be controlled by changing the excitation wavelengths to exclude the absorbance of one of the molecular crystals. PDI can be selectively excited using light above 550 nm and both PDI and DCA act simply as passive waveguides for light in the infrared region of the spectrum, of particular importance for wireless communication. This study represents an exciting next step for organic molecular materials as optical waveguides with a new architecture for devices.

To find out more please read:

A filled organic crystal as a hybrid large-bandwidth optical waveguide

Luca Catalano, Patrick Commins, Stefan Schramm, Durga Prasad Karothu, Rachid Rezgui, Kawther Hadef and Panče Naumov

Chem. Commun, 2019, 55, 4921-4924.

About the blogger:

Beth Mundy is a PhD candidate in chemistry in the Cossairt lab at the University of Washington in Seattle, Washington. Her research focuses on developing new and better ways to synthesize nanomaterials for energy applications. She is often spotted knitting in seminars or with her nose in a good book. You can find her on Twitter at @BethMundySci.

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HOT Chemical Communication articles for April

All of the referee-recommended articles below are free to access until  15th August 2019.

Drastic lattice softening in mixed triazole ligand iron(II) spin crossover nanoparticles
Mario Piedrahita-Bello, Karl Ridier, Mirko Mikolasek, Gábor Molnár, William Nicolazzi, Lionel Salmon* and Azzedine Bousseksou*
Chem. Commun., 2019, 55, 4769-4772
DOI: 10.1039/C9CC01619H, Communication

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Highly symmetrical, 24-faceted, concave BiVO4 polyhedron bounded by multiple high-index facets for prominent photocatalytic O2 evolution under visible light
Jianqiang Hu, Huichao He, Liang Li, Xin Zhou,* Zhaosheng Li,* Qing Shen, Congping Wu, Adullah M. Asiri, Yong Zhou* and Zhigang Zou
Chem. Commun., 2019, 55, 4777-4780
DOI: 10.1039/C9CC01366K, Communication

 

 

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Controlling the morphological evolution of a particle-stabilized binary-component system
Tao Li,* Jason Klebes, Jure Dobnikar* and Paul S. Clegg
Chem. Commun., 2019, 55, 5575-5578
DOI: 10.1039/C9CC01519A, Communication

 

 

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Formation of enantioenriched alkanol with stochastic distribution of enantiomers in the absolute asymmetric synthesis under heterogeneous solid–vapor phase conditions
Yoshiyasu Kaimori, Yui Hiyoshi, Tsuneomi Kawasaki, Arimasa Matsumoto and Kenso Soai*
Chem. Commun., 2019, 55, 5223-5226
DOI: 10.1039/C9CC01875A, Communication

 

 

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Rapid screening of the hydrogen bonding strength of radicals by electrochemiluminescent probes
Qinghong Xu, Jiali Liang, Xu Teng, Xin Yue, Ming Lei, Caifeng Ding and Chao Lu*
Chem. Commun., 2019, 55, 5563-5566
DOI: 10.1039/C9CC01210A, Communication

 

 

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Photo-oxygenation inhibits tau amyloid formation
Takanobu Suzuki, Yukiko Hori, Taka Sawazaki, Yusuke Shimizu, Yu Nemoto, Atsuhiko Taniguchi, Shuta Ozawa, Youhei Sohma,* Motomu Kanai* and Taisuke Tomita*
Chem. Commun., 2019, 55, 6165-6168
DOI: 10.1039/C9CC01728C, Communication

 

 

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4th Annual UK Porous Materials Conference

This July saw the 4th Annual UK Porous Materials Conference (UKPorMat) held in Cardiff (1st-2nd July) by the RSC Porous Materials Interest Group!

The Annual UK Porous Materials Conference (UKPorMat), now in its 4th year, was held at Cardiff University on the 1st and 2nd of July 2019. The meeting, organised and chaired by the committee members of the RSC Porous Materials Interest Group, aims to bring together researchers working in the expanding field of porous materials, which includes metal-organic frameworks (MOFs), covalent-organic frameworks (COFs), porous organic cages, porous organic polymers, polymers of intrinsic microporosity and much more.

The Royal Society of Chemistry was delighted to be a part of the event, sponsoring a number of poster and talk prizes:

  • Giulia Schukraft (Imperial College London) was awarded the ChemComm Poster Prize
  • Iona Doig (University of Southampton) was awarded the Materials Horizons Poster Prize
  • Alexander Thom (University of Glasgow) was awarded the CrystEngComm Poster Prize
  • Alex James (University of Sheffield) was awarded the Chemical Science Prize for Best Talk

Congratulations to all of the prize winners!

 

Giulia Schukraft (left) receiving the ChemComm prize from Chris Harding (right)

Iona Doig (right) receiving the Materials Horizons prize from Chris Harding (left)

Alexander Thom (left) receiving the CrystEngComm prize from Ross Forgan (right) Alex James (left) receiving the Chemical Science prize from Chris Harding (right)

Special thanks to the organizers and committee members of the RSC Porous Materials Interest Group:

Dr Thomas Bennett (University of Cambridge)

Dr Andrea Laybourn (University of Nottingham)

Dr Ross Forgan (University of Glasgow)

Dr Darren Bradshaw (University of Southampton)

Dr Tim Easun (Cardiff University)

Dr Timothy Johnson (Johnson Matthey Technology Centre)

Professor Tina Düren

Prize-winners at the close of the 4th Annual UK Porous Materials meeting (Cardiff, 1st-2nd July 2019)

 

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