Archive for the ‘Uncategorized’ Category

Finding early warnings in chemical systems

Our world runs on systems of ever-increasing complexity, be they natural or human created. Their behavior can generally be modeled and operates within a normal range… until it hits a tipping point at a border between two behavioral regimes. Once that threshold is reached the system acts in dramatically different, and often destructive, ways. However, there are often warning signs right around the tipping point that can serve to alert careful observers that the danger zone is near. By finding ways to identify and monitor this behavior either contingency plans can be put in place or the problem corrected before it becomes catastrophic. While much of this has been studied for large systems like the stock market or ecosystems, researchers recently applied this to chemical systems.

The utility of identifying early warning signals isn’t limited to preventing massive changes; it can also help bound regions of different functionality in chemical systems. To explore this, researchers used a trypsin oscillator system they previously developed that has two modes of flow (Figure 1), either sustained oscillations in trypsin concentration or dampened oscillations that eventually lead to a steady concentration of trypsin. By changing flow rate, temperature, or reagent concentration the researchers could tune the behavior of the system to test either active or passive monitoring schemes to find early warning signs. Since they knew what conditions produced each mode, they could operate the system right at the boundary and watch its behavior.

Figure 1. Schematic of trypsin system with examples of oscillation patterns.

In the “active” experiments the researchers intervened in the system’s normal functioning and watched how its response, the “critical slow down phenomena,” changed as the conditions were brought closer to the boundary. In “passive” experiments, the researchers simply brought the system close to the boundary and monitored the shape of the oscillation waves focusing on their full-width half maxima (FWHM). In the series of active sensing experiments, the researchers waited to see how long it took the system to re-establish sustained oscillations after a change in temperature. They expected to see this recovery time increase as the system was brought closer to the edge, aka the “critical slow down phenomena.” In their experiment they elevated the temperature of the system to 49.0 oC and observed how long it took to recover to either 24.3 oC (well within the sustained regime) or 20.9 oC (near the behavioral boundary). They saw the expected dramatic increase in time to return to sustained oscillation, with the system recovering in 10.7 hrs at 24.3 oC, but taking three times as long, 32.8 hrs, when the final temperature was 20.9 oC (Figure 2). The experimental results were further validated by theoretical modeling, where experimentally challenging positions at the very edge of the boundary could be explored and showed the same general behavior.

Figure 2. Top: active monitoring experiments at two different temperatures showing the differences in time needed to recover sustained oscillations. Bottom: comparison of modeled and experimental recovery times.

The theoretical modeling was further used to create a map of passive monitoring space, looking at the variations in FWHM. They saw that as the system moves away from the center of the oscillation regime the FWHM increases as the peaks broaden. This becomes more pronounced as the conditions approach the behavioral boundary. This provides a baseline knowledge with multiple types of measurements to compare the stability of the simple system over a range of conditions. Additionally, this system and others like it can serve as the base for modeling more complex systems of which they are a part.

To find out more, please read:

Early warning signals in chemical reaction networks

Chem. Commun., 2020, Advance Article

Oliver R. Maguire, Albert S. Y. Wong, Jan Harm Westerdiep and Wilhelm T. S. Huck

About the blogger:

Dr. Beth Mundy recently received her PhD in chemistry from the Cossairt lab at the University of Washington in Seattle, Washington. Her research focused 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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The Cram Lehn Pedersen Prize in Supramolecular Chemistry


 

The International Committee of the International Symposium on Macrocyclic and Supramolecular Chemistry is pleased to invite nominations for the Cram Lehn Pedersen Prize for young supramolecular chemists.

The Cram Lehn Pedersen Prize, named in honor of the winners of the 1987 Nobel Prize in Chemistry, will recognise significant original and independent work in supramolecular chemistry.

Those who were awarded their PhD on or after 1st January 2009 (or who have an award of PhD date together with allowable career interruptions* that would be commensurate with award of their PhD on or after 1st January 2009) are eligible for the 2020 award. The winner will receive a prize of £2000 and free registration for the ISMSC meeting in Sydney, Australia. In addition to giving a lecture at ISMSC, a short lecture tour will be organized after the meeting in consultation with the Editor of Chemical Communications, the sponsor of the award.

Nomination Details

You may nominate yourself, but a nomination letter is recommended. Nomination materials should include: CV, list of publications (divided into publications from your PhD and post-doc, and those from your independent work), and be sent to Prof. Roger Harrison (ISMSC Secretary) at roger_harrison@byu.edu by 31st December 2019.

*Allowable career interruptions include primary caregiver’s responsibilities, illness, disability or parental leave and must be outlined in a cover letter with supporting documentation. See  https://www.chem.byu.edu/faculty-and-staff/resources/international-symposium-on-macrocyclic-and-supramolecular-chemistry/awards/ for specific details.

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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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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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4th Annual UK Porous Materials Conference

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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ChemComm: Our Vision

Vision statement

“ChemComm is the Royal Society of Chemistry’s most cited journal, and has a long history of publishing exciting new findings of exceptional significance, across the breadth of chemistry.

With its Communication format, we recognise the importance of rapid disclosure of your work, and we are proud that our times to publication remain among the fastest in the field.

Our vision for ChemComm is to maintain our longstanding tradition of quality, trust and fairness, and we encourage you to join our community by publishing your most exciting research with us.”

Véronique Gouverneur, Editorial Board Chair

Scope

ChemComm is committed to publishing findings on new avenues of research, drawn from all major areas of chemical research, from across the world. Main research areas include (but are not limited to):

  • Analytical chemistry
  • Biomaterials chemistry
  • Bioorganic/medicinal chemistry
  • Catalysis
  • Chemical Biology
  • Coordination Chemistry
  • Crystal Engineering
  • Energy
  • Sustainable chemistry
  • Green chemistry
  • Inorganic chemistry
  • Inorganic materials
  • Main group chemistry
  • Nanoscience
  • Organic chemistry
  • Organic materials
  • Organometallics
  • Physical chemistry
  • Supramolecular chemistry
  • Synthetic methodology
  • Theoretical and computational chemistry

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

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

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Targeting the Powerhouse of the Cell to Fight Cancer

Everyone knows that cancer as a disease is awful, but the side effects of currently utilized chemotherapies have their own horrors. Research into natural products as therapies have found some promising compounds, but they face barriers to practical use in patients. One particular molecule, artesunate (ART), recently showed high potential for anticancer activity when in the presence of iron. Unfortunately, ART has major problems that limit its current applicability, including low solubility in water and high instability in biologically relevant conditions.

One approach to get around these issues is to encapsulate the drug (pun intended) in a nanoparticle-based carrier. A carrier with a hydrophobic interior and hydrophilic exterior can bring higher concentrations of drugs with low solubility into a cell and protect them from deleterious conditions in the body. An additional benefit is the relative ease of incorporating targeting ligands into the particles during synthesis. This allows the drugs to only interact with specific cells or, in this specific case, the mitochondria within cells.

Figure 1. Schematic of the nanoparticle synthesis process complete with targeting ligand molecules. The anticancer agent is activated in the presence of iron.

Researchers in China have prepared approximately 200 nm nanoparticle carriers for ART (Figure 1) using triphenyl phosphonium (TPP) as a mitochondrial targeting ligand. These nanoparticles remained stable in biologically relevant conditions for a week, sufficient for in-vitro studies. The studies showed significant decreases in cancer cell growth when the nanoparticles were used compared to the ART alone. The nanoparticles with TPP on the surface showed the highest efficacy, particularly when coupled with iron treatment to activate the ART.

Figure 2. Images of cells exposed to nanoparticles with (bottom) and without (top) a targeting ligand filled with different fluorescent dyes. The increased brightness corresponds to higher uptake of the nanoparticles by the cells.

To further investigate the cell uptake pathway of the nanoparticles, the researchers added fluorescent dye molecules to the inside of the particles. Once the cells took up and ruptured the nanoparticles, the dyes were released and became visible to the researchers (Figure 2). The fluorescence was twice as great in cells exposed to the nanoparticles treated with the TPP targeting ligand, showing its value for cell uptake. The researchers also used fluorescent dyes that react with reactive oxygen species (ROSs), as their generation is how ART kills cancer cells. The in-vitro studies showed an over three-fold increase in fluorescence from reactions with ROSs which, combined with data showing higher rates of cell death, supports the increased activity of ART when combined with this nanoparticle architecture.

To find out more please read:

A mitochondria targeting artesunate prodrug-loaded nanoparticle exerting anticancer activity via iron-mediated generation of the reactive oxygen species

Zhigang Chen, Xiaoxu Kang, Yixin Wu, Haihua Xiao, Xuzi Cai, Shihou Seng, Xuefeng Wang and Shiguo Chen

Chem. Commun., 2019, 55, 4781 – 4784.

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 ChemComm articles for October

All of the referee-recommended articles below are free to access until 7th December 2018.

Essential but sparse collagen hydroxylysyl post-translational modifications detected by DNP NMR
Wing Ying Chow, Rui Li, Ieva Goldberga, David G. Reid, Rakesh Rajan, Jonathan Clark, Hartmut Oschkinat, Melinda J. Duer, Robert Hayward and Catherine M. Shanahan
Chem. Commun., 2018,54, 12570-12573
DOI: 10.1039/C8CC04960B, Communication

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Rapid synthesis of Co3O4 nanosheet arrays on Ni foam by in situ electrochemical oxidization of air-plasma engraved Co(OH)2 for efficient oxygen evolution
Wenling Gu, Liuyong Hu, Xiaoqing Zhu, Changshuai Shang, Jing Li and Erkang Wang
Chem. Commun., 2018, Advance Article
DOI: 10.1039/C8CC06399K, Communication

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Modification of amine-cured epoxy resins by boronic acids based on their reactivity with intrinsic diethanolamine units
Yumiko Ito, Jumpei Kida, Daisuke Aoki and Hideyuki Otsuka
Chem. Commun., 2018, Advance Article
DOI: 10.1039/C8CC07412G, Communication

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3-Homoacyl coumarin: an all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition
Yi-Ru Chen, Madhusudhan Reddy Ganapuram, Kai-Hong Hsieh, Kai-Han Chen, Praneeth Karanam, Sandip Sambhaji Vagh, Yan-Cheng Liou and Wenwei Lin
Chem. Commun., 2018, Advance Article
DOI: 10.1039/C8CC07271J, Communication

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Coinage metal complexes of NHC-stabilized silyliumylidene ions
Philipp Frisch and Shigeyoshi Inoue
Chem. Commun., 2018, Advance Article
DOI: 10.1039/C8CC07754A, Communication

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An ultrafine ruthenium nanocrystal with extremely high activity for the hydrogen evolution reaction in both acidic and alkaline media
Yutong Li, Fuqiang Chu, Yang Liu, Yong Kong, Yongxin Tao, Yongxin Li and Yong Qin
Chem. Commun., 2018, Advance Article
DOI: 10.1039/C8CC08276F, Communication

 

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