Skipped Dienes: Stereoselective Approach to Polyene Macrocycles

Tezcan Guney writes for the ChemComm blog about a recent ChemComm article

C5CC02091C GA

Most organic chemists asked to imagine a macrocycle with 19 atoms in the backbone, and with three alkenes and one alkyne, would likely place at least two of the alkenes in conjugation, especially if they were familiar with macrolide antibiotic rifamycin

Conjugated dienes are usually perceived as most stable; naturally-occurring macrocycles with skipped or non-conjugated dienes are a synthetically challenging class of compounds with biological activity.

In a recent Chemical Communications article, the research groups of Professor Ian Fairlamb and Professor Richard Taylor describe an elegant regio- and stereoselective synthetic approach to an analogue of 19-membered macrocycle phacelocarpus 2-pyrone A. The target compound is distinctly challenging due to its unique, multiple 1,4-pattern of skipped alkene and alkyne functionality.

Several effective synthetic campaigns of 1,4-diene motifs capitalize on alkene/alkyne metathesis or cross-coupling strategies. However, most methods lack stereoselectivity. In contrast, Fairlamb, Taylor and co-workers achieved the construction of the macrocycle in 6.5% yield over 11 steps in the longest linear route.  In doing so, they stereoselectively combined three fragments in the first use of bifunctional (Z)-vinylstannyl-posphonium salt as a nucleophile with stepwise Wittig and Stille reactions. 

The successful Z-stereoselectivity of the Wittig reaction was accompanied by the full retention of the Z-vinyl stannane functionality.  While stereoselectivity in the Stille cross-coupling was anticipated as problematic due to the sensitive nature of the allylic vinyl ether moiety in the substrate, the authors were pleased that the macrocyclization succeeded with an E:Z ratio of 5:1.

To discover all the synthetic details about the chemistry from the Fairlamb and Taylor groups, read the ChemComm article in full – it’s free to access* until 3rd July:
Macrocyclic polyenynes: a stereoselective route to vinyl-ether-containing skipped diene systems
Thomas O. Ronson, Martin H. H. Voelkel, Richard J. K. Taylor and Ian J. S. Fairlamb
Chem. Commun., 2015, 51, 8034-8036
DOI: 10.1039/C5CC02091C

Also of interest may be the recently published Chemical Science Perspective Article “Macrocycles: lessons from the distant past, recent developments, and future directions” by Organic and Biomolecular Chemistry Editorial Board Chair Professor Andrei K. Yudin (Chem. Sci., 2015, 6, 30-49).

*Access is free through a registered RSC account – click here to register


Dr. Tezcan Guney is a web writer for Chemical Society Reviews, Chemical Science and Chemical Communications. Dr. Guney received his Ph.D. from the Department of Chemistry at Iowa State University with Prof. George Kraus, where he focused on the synthesis of biologically active polycyclic natural products and multifunctional imaging probes. Currently, he is a postdoctoral research scholar at the Memorial Sloan-Kettering Cancer Center in New York with Prof. Derek Tan, contributing to the efforts to access biologically active small molecules using the diversity-oriented synthetic approach.

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ACIN 2015 Conference

Are you ready for the third International Conference on Advanced Complex Inorganic Nanomaterials? This exciting conference will be held from the 13th to the 17th of July at the University of Namur, in Belgium.

ChemComm proudly sponsors this conference, which will offer an update of recent innovations in both fundamental and applied aspects and to highlight the latest advances and progress in the field of inorganic nanomaterials, such as inorganics, ceramics, hybrids and bio-inspired materials.

Additionally, Can Li, Associate Editor of the journal, will be giving a talk in this fantastic conference, in addition to presenting a ChemComm Poster Prize. He is Professor of Chemical Physics at the Dalian Institute of Chemical Physics (Chinese Academy of Sciences, China).

He works on fundamental and applied research in catalysis and making efforts to reveal the essential relationship between catalytic performance and catalyst structure, and try to understand catalysis at various levels including atomic, molecular as well as nanometer scales and to apply these understandings to the designs and the development of practical applications in energy, fine chemicals and environmental sciences.


Read some of his latest articles in ChemComm:

Construction of unique six-coordinated titanium species with an organic amine ligand in titanosilicate and their unprecedented high efficiency for alkene epoxidation
Le Xu, Da-Ding Huang, Chen-Geng Li, Xinyi Ji, Shaoqing Jin, Zhaochi Feng, Fei Xia, Xiaohong Li, Fengtao Fan, Can Li and Peng Wu
Chem. Commun.
, 2015,51, 9010-9013
DOI: 10.1039/C5CC02321A, Communication

Nitrogen-doped carbon nanotubes with metal nanoparticles as counter electrode materials for dye-sensitized solar cells
Yedi Xing, Xiaojia Zheng, Yihui Wu, Mingrun Li, Wen-Hua Zhang and Can Li
Chem. Commun.
, 2015,51, 8146-8149
DOI:
10.1039/C5CC01379H, Communication

Photocatalytic aerobic oxidation of amines to imines on BiVO4 under visible light irradiation
Bo Yuan, Ruifeng Chong, Bao Zhang, Jun Li, Yan Liu and Can Li
Chem. Commun.
, 2014,50, 15593-15596
DOI:
10.1039/C4CC07097F, Communication


Submit your next top-notch, high impact Communication to

Can Li’s Editorial Office

ChemComm is the home of urgent high quality communications from across the chemical sciences. With a world-renowned reputation for quality and fast times to publication (average of 40 days), ChemComm is the ideal place to publish your research.

We look forward to seeing you in Namur!


Stay up to date with ChemComm: Be among the first to hear about the newest articles being published – Sign-up to our journal news alert to receive information about most read articles, themed issues, journal news, as well as calls for papers and invitations. Follow us on Twitter!

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Taking the lead on drug discovery

Katrina Krämer writes about a hot ChemComm article for Chemistry World

Researchers from the UK have developed a straightforward strategy for making compounds that have the potential to become clinical drugs. By cleverly combining robust chemistry and simple starting materials, the team accessed numerous small, diverse molecules with properties suitable for drug screening.

Even the most successful drug starts small. Pharmaceutical companies screen vast libraries of small compounds for the next lead – a molecule that interacts with a given target such as a protein or receptor. Through structural optimisation, tweaking and testing, the lead then grows into a full-fledged drug, ready for biological trials.

A minimal toolkit of reactions turns small polyfunctional molecules into diverse scaffolds


Read the full article in Chemistry World»

Read the original journal article in ChemComm – it’s free to access until 1st July:
Synthesis of amphiphilic polysuccinimide star copolymers for responsive delivery in plants
Mingsheng Chen, Shaun P. Jensen, Megan R. Hill, Gloria Moore, Zhenli He and Brent S. Sumerlin 
Chem. Commun., 2015, Advance Article
DOI: 10.1039/C5CC02726H, Communication

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Star creation for plant medication

Anisha Ratan writes about a hot ChemComm article for Chemistry World

US scientists have developed a stimuli-responsive, biodegradable star-shaped copolymer for targeted nutrient and pesticide delivery in plants. Controlled release to the phloem at an elevated pH makes these nanocarriers a promising step forward in modern agriculture.

Polymeric nanocarriers have already been studied for site-specific and controlled drug release in medicine, but their agricultural potential remains relatively unexplored. Existing methods of plant nutrient and pesticide delivery offer low efficiency so a site-specific strategy is in demand.


Read the full article in Chemistry World»

Read the original journal article in ChemComm – it’s free to access until 29th June:
Synthesis of amphiphilic polysuccinimide star copolymers for responsive delivery in plants
Mingsheng Chen, Shaun P. Jensen, Megan R. Hill, Gloria Moore, Zhenli He and Brent S. Sumerlin 
Chem. Commun., 2015, Advance Article
DOI: 10.1039/C5CC02726H, Communication

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Top 25 ChemComm articles January–March 2015

The 25 most-downloaded ChemComm articles in the first quarter of 2015 were as follows: 

Nanoimaging of localized plasmon-induced charge separation
Emiko Kazuma, Nobuyuki Sakai and Tetsu Tatsuma 
Chem. Commun., 2011,47, 5777-5779
DOI: 10.1039/C1CC10936G, Communication 

Glucose transport machinery reconstituted in cell models
Jesper S. Hansen, Karin Elbing, James R. Thompson, Noah Malmstadt and Karin Lindkvist-Petersson 
Chem. Commun., 2015,51, 2316-2319
DOI: 10.1039/C4CC08838G, Communication 

An engineered lantipeptide synthetase serves as a general leader peptide-dependent kinase
Gabrielle N. Thibodeaux and Wilfred A. van der Donk 
Chem. Commun., 2012,48, 10615-10617
DOI: 10.1039/C2CC34138G, Communication 

A solvent-free Diels–Alder reaction of graphite into functionalized graphene nanosheets
Jeong-Min Seo and Jong-Beom Baek 
Chem. Commun., 2014,50, 14651-14653
DOI: 10.1039/C4CC07173E, Communication 

Nanostructured electrochromic smart windows: traditional materials and NIR-selective plasmonic nanocrystals
Evan L. Runnerstrom, Anna Llordés, Sebastien D. Lounis and Delia J. Milliron 
Chem. Commun., 2014,50, 10555-10572
DOI: 10.1039/C4CC03109A, Feature Article 

Production of few-layer phosphorene by liquid exfoliation of black phosphorus
Jack R. Brent, Nicky Savjani, Edward A. Lewis, Sarah J. Haigh, David J. Lewis and Paul O’Brien 
Chem. Commun., 2014,50, 13338-13341
DOI: 10.1039/C4CC05752J, Communication 

Polydiacetylenes: supramolecular smart materials with a structural hierarchy for sensing, imaging and display applications
Oktay Yarimaga, Justyn Jaworski, Bora Yoon and Jong-Man Kim 
Chem. Commun., 2012,48, 2469-2485
DOI: 10.1039/C2CC17441C, Feature Article 

Hydrogen storage properties and neutron scattering studies of Mg2(dobdc)—a metal–organic framework with open Mg2+ adsorption sites
Kenji Sumida, Craig M. Brown, Zoey R. Herm, Sachin Chavan, Silvia Bordiga and Jeffrey R. Long 
Chem. Commun., 2011,47, 1157-1159
DOI: 10.1039/C0CC03453C, Communication
From themed collection Hydrogen 

A high-throughput screening method for determining the substrate scope of nitrilases
Gary W. Black, Nicola L. Brown, Justin J. B. Perry, P. David Randall, Graeme Turnbull and Meng Zhang 
Chem. Commun., 2015,51, 2660-2662
DOI: 10.1039/C4CC06021K, Communication 

Enhancement of cyclization quantum yields of perfluorodiarylethenes via weak intramolecular interactions
Shouzhi Pu, Chunhong Zheng, Qi Sun, Gang Liu and Congbin Fan 
Chem. Commun., 2013,49, 8036-8038
DOI: 10.1039/C3CC44348E, Communication 

Rapid ultrasonic isothermal amplification of DNA with multiplexed melting analysis – applications in the clinical diagnosis of sexually transmitted diseases
Gaolian Xu, Rory N. Gunson, Jonathan M. Cooper and Julien Reboud 
Chem. Commun., 2015,51, 2589-2592
DOI: 10.1039/C4CC08389J, Communication 

A zirconium squarate metal–organic framework with modulator-dependent molecular sieving properties
Bart Bueken, Helge Reinsch, Nele Reimer, Ivo Stassen, Frederik Vermoortele, Rob Ameloot, Norbert Stock, Christine E. A. Kirschhock and Dirk De Vos 
Chem. Commun., 2014,50, 10055-10058
DOI: 10.1039/C4CC03764B, Communication 

Highly sensitive detection of self-aggregated single-walled carbon nanotubes using a DNA-immobilized resonator
Kuewhan Jang, Jinsung Park, Doyeon Bang, Sangmyung Lee, Juneseok You, Seungjoo Haam and Sungsoo Na 
Chem. Commun., 2013,49, 8635-8637
DOI: 10.1039/C3CC42911C, Communication 

Selective glucose recognition by boronic acid azoprobe/γ-cyclodextrin complexes in water
Chie Shimpuku, Rimiko Ozawa, Akira Sasaki, Fuyuki Sato, Takeshi Hashimoto, Akiyo Yamauchi, Iwao Suzuki and Takashi Hayashita 
Chem. Commun., 2009, 1709-1711
DOI: 10.1039/B819938H, Communication 

Nickel-catalyzed borylation of arenes and indoles via C–H bond cleavage
Takayuki Furukawa, Mamoru Tobisu and Naoto Chatani 
Chem. Commun., 2015,51, 6508-6511
DOI: 10.1039/C5CC01378J, Communication 

Graphene quantum dots: emergent nanolights for bioimaging, sensors, catalysis and photovoltaic devices
Jianhua Shen, Yihua Zhu, Xiaoling Yang and Chunzhong Li 
Chem. Commun., 2012,48, 3686-3699
DOI: 10.1039/C2CC00110A, Feature Article 

Enhanced stability and activity of Pt–Y alloy catalysts for electrocatalytic oxygen reduction
Sung Jong Yoo, Soo-Kil Kim, Tae-Yeol Jeon, Seung Jun Hwang, June-Gunn Lee, Seung-Cheol Lee, Kug-Seung Lee, Yong-Hun Cho, Yung-Eun Sung and Tae-Hoon Lim 
Chem. Commun., 2011,47, 11414-11416
DOI: 10.1039/C1CC12448J, Communication 

Synthesis and characterization of dithienylbenzobis(thiadiazole)-based low band-gap polymers for organic electronics
Heong Sub Oh, Tae-Dong Kim, Yun-Hyuk Koh, Kwang-Sup Lee, Shinuk Cho, Alex Cartwright and Paras N. Prasad 
Chem. Commun., 2011,47, 8931-8933
DOI: 10.1039/C1CC11899D, Communication 

Aggregation-induced emission: phenomenon, mechanism and applications
Yuning Hong, Jacky W. Y. Lam and Ben Zhong Tang 
Chem. Commun., 2009, 4332-4353
DOI: 10.1039/B904665H, Feature Article 

Construction of a supported Ru complex on bifunctional MOF-253 for photocatalytic CO2 reduction under visible light
Dengrong Sun, Yanhong Gao, Jinlong Fu, Xianchong Zeng, Zhongning Chen and Zhaohui Li 
Chem. Commun., 2015,51, 2645-2648
DOI: 10.1039/C4CC09797A, Communication 

Chemical synthesis of magnetic nanoparticles
Taeghwan Hyeon 
Chem. Commun., 2003, 927-934
DOI: 10.1039/B207789B, Feature Article 

Multifunctional catalysis by Pd-polyoxometalate: one-step conversion of acetone to methyl isobutyl ketone
Robert D. Hetterley, Elena F. Kozhevnikova and Ivan V. Kozhevnikov 
Chem. Commun., 2006, 782-784
DOI: 10.1039/B515325E, Communication 

Reduction of graphene oxide viaL-ascorbic acid
Jiali Zhang, Haijun Yang, Guangxia Shen, Ping Cheng, Jingyan Zhang and Shouwu Guo 
Chem. Commun., 2010,46, 1112-1114
DOI: 10.1039/B917705A, Communication 

Naphthalene and perylene diimides for organic transistors
Frank Würthner and Matthias Stolte 
Chem. Commun., 2011,47, 5109-5115
DOI: 10.1039/C1CC10321K, Highlight
From themed collection Highlights in Chemistry 

Wet chemical synthesis of silver nanorods and nanowires of controllable aspect ratio
Nikhil R. Jana, Latha Gearheart and Catherine J. Murphy 
Chem. Commun., 2001, 617-618
DOI: 10.1039/B100521I, Communication 

These articles are all free to download until 6th July. Access is free through a registered RSC account – click here to register 


 

ChemComm is the home of urgent high quality communications from across the chemical sciences. With a world renowned reputation for quality and fast times to publication (average of 40 days), ChemComm is the ideal place to publish your research. 

Submit your urgent research to ChemComm today! 

Stay up to date with ChemComm
Be among the first to hear about the newest articles being published – Sign-up to our journal news alert to receive information about most read articles, themed issues, journal news, as well as calls for papers and invitations.

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Meet our authors: an interview with Kamil Godula

Welcome to a new entry on our series of interviews in the ChemComm blog! We want you to know more about some of the early career investigators who choose to publish their exciting work with us.

Next in this series is Dr Kamil Godula, from the University of California San Diego. Read the full interview below.

———-

What inspired you to become a scientist?Kamil Godura

For me, it was my curiosity in finding out how the world around me works. My science teachers seemed to be the ones that had the answers to many of my questions and that had inspired me to pursue a scientific path.

I’ve always been intrigued by the ability of biologists, physicists and mathematicians to describe our world and try to pinpoint its fundamental principles. But ultimately, it was chemistry that captured my imagination for being a transformative science rather than a descriptive one. Becoming a chemist has allowed me to unleash my creativity and imagination.

Follow us on Twitter!How did you find out about ChemComm?

I became familiar with ChemComm as a new graduate student. Ever since, I’ve enjoyed the high quality of the research papers and the broad scope of topics that appear in the journal. Reading ChemComm is always a great way to gain a fresh perspective on and a new inspiration for my research.

What was the motivation behind the work described in your article? What interested you in this area?

My research team is interested in studying the role of carbohydrates in modulating biological events at the boundary between cells and their surrounding environment. The structures of these glycans, as they are called, can be recognized by protein receptors and many pathogens have evolved to target glycans to gain entry into their hosts.

What is interesting is the fact that the interactions of individual glycans and proteins are typically rather weak to be specific in a biological setting. To compensate for that, multiple copies of glycans are typically displayed by lipids and proteins found on cell membranes. My lab is interested in understanding how the three dimensional presentation of glycans on our cells affects the ability of influenza viruses to bind and initiate infection.

Once we gain a better understanding of these higher-order binding interactions between the virus and our cells, we may be able to design better drugs to fight influenza.

Reading ChemComm is always a great way to gain a fresh perspective on and a new inspiration for my research.

Dr Kamil Godula, University of California San Diego

Why did you choose ChemComm to publish your work?

Our research is very interdisciplinary and involves carbohydrate and polymer synthesis, microarray platform development, as well as virus production and biological assays. At the same time, chemistry is always the central enabling science in all of our research. Therefore, ChemComm was a natural choice to publish our study.

Where do you see your research heading next?

Wikipedia

Our microarray platform has begun to reveal very interesting effects of glycan organization on their recognition by intact influenza viruses. We are currently investigating how the initial binding of the viruses to the “sugar landing pad” on epithelial cells correlates with their ability to enter the cells and initiate infection. We are also expanding this platform to enable the discovery of more effective antiviral drugs.

If you could not be a scientist, but could be anything else, what would you be?

Definitely a jazz musician. Benny Goodman has always been my great inspiration; I’m fascinated by the complexity and beauty of his improvisations and wonder what it’d feel like to master the clarinet the way he did.

———-

Did you enjoy Kamil’s story, or do you have your own memorable story about your first ChemComm paper? Tweet us @ChemCommun (#meetCCauthors) or reply in the comments below!

ChemComm fully supports researchers in the early stage of their careers, and remains the leading journal for urgent high-quality communications from across the chemical sciences.

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Terpene analogues bear safer pesticides

Image of ants crawling over a plantTweaking the natural substrates of terpene synthase enzymes could lead to less toxic pesticides and swathes of other important biologically-active compounds, according to UK researchers.

Terpene synthases generate a huge variety of natural compounds with important functions in all forms of life. Many plants emit volatile terpenes to repel predators, including insects, so there is considerable interest in creating new terpene analogues for pesticides. Insects, however, have a very sophisticated ‘nose’ for these compounds and may ignore even closely-related analogues.


Read the full article in Chemistry World»

Read the original journal article ChemComm – it’s free to access until 22nd June:
Novel olfactory ligands via terpene synthases
Sabrina Touchet, Keith Chamberlain, Christine M. Woodcock, David J. Miller, Michael A. Birkett, John A. Pickett and Rudolf K. Allemann 
Chem. Commun., 2015,51, 7550-7553
DOI: 10.1039/C5CC01814E, Communication

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Hierarchical 3D immunoassays – higher loading, lower fouling

Iain Larmour is a guest web writer for ChemSci. He has researched a wide variety of topics during his years in the lab including nanostructured surfaces for water repellency and developing nanoparticle systems for bioanalysis by surface enhanced optical spectroscopies. He currently works in science management. In his spare time he enjoys reading, photography, art and inventing.

If you are producing an immunoassay there are two key parameters you need to understand and optimise: surface structure and surface chemistry. Get these two parameters right and you will optimise the sensitivity of your immunoassay. 

Although there have been a multitude of 3D surface generation routes reported, they are generally complicated and require a lot of additional steps. Although these 3D surfaces lead to high probe loading levels they also often lead to high levels of non-specific protein absorption, undoing any good the surface structure would have led to. 

Jinghua Yin and team from the State Key Laboratory of Polymer Physics and Chemistry at the Changchun Institute of Applied Chemistry have focussed on both properties to generate a much improved immunoassay. 

 Firstly they generated a 3D surface using UV irradiation of polystyrene spheres onto a substrate; they then grafted polymer brushes to the sphere surface. The polymer brushes not only further increased the surface area (more than doubling it from the bare sphere surface) but also acted as an anti-fouling agent, reducing the amount of non-specific binding observed by up to 90%. 

Antibody loading on different surface types showing increasing loading levels

 

The commonality of the functional groups on the polymer brushes mean that any antibody can be attached to the prepared surface. To find out the details of how to make these surfaces and try them out on your own immunoassays, read the paper today!


To read the details, check out the ChemComm article in full:
Facile fabrication of microsphere-polymer brush hierarchically three-dimensional (3D) substrates for immunoassays
Jiao Ma, Shifang Luan, Lingjie Song, Shuaishuai Yuan, Shunjie Yan, Jing Jin and Jinghua Yin
Chem. Commun., 2015, 51, 6749-6752
DOI: 10.1039/C5CC01250C

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Sweating the small stuff – paper-based cystic fibrosis screening

Iain Larmour is a guest web writer for ChemSci. He has researched a wide variety of topics during his years in the lab including nanostructured surfaces for water repellency and developing nanoparticle systems for bioanalysis by surface enhanced optical spectroscopies. He currently works in science management. In his spare time he enjoys reading, photography, art and inventing.

Cystic Fibrosis (CF) is one of the most common inherited diseases, with 1 in 3000 Caucasians a carrier of the single gene mutation. One feature of CF is abnormally elevated sweat anions, and this feature is exploited in the gold standard diagnostic tests.
 
However, gold standard in this case does not stand for inexpensive nor ease of use. This leads to limited availability and the requirement for large volumes of sweat; not the easiest of things to get from newborn babies who need to be screened for CF.
 
In a recent ChemComm article, Xuan Mu, Zhi Zheng and team from the Institute of Basic Medical Sciences at Peking Union Medical College have reported the development of a paper-based analytical device that can detect sweat on the skin using much smaller volumes than current tests.
 
The team use a colorimetric detection approach with stacked functional papers (paper discs produced with a hole punch). The key element is the anion exchange layer which converts sweat anions into hydroxide ions, leading to a local alkalization and subsequent change in the colour of another pH paper layer. 
 

The stacked paper based diagnostic device developed by the authors


The authors have applied their diagnostic device to real patients and can clearly discriminate between CF and non-CF patients with a clinical reference point. With the cost of these tests being less than a dollar and being wearable, the authors have opened up a new opportunity for the screening of CF.
 
To read the details, check out the ChemComm article in full:
 
A paper-based skin patch for the diagnostic screening of cystic fibrosis
Xuan Mu, Xiaolei Xin, Chengyan Fan, Xue Li, Xinlun Tian, Kai-Feng Xu and Zhi Zheng
Chem. Commun., 2015, 51, 6365-6368
DOI: 10.1039/C5CC000717H

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Ionic liquids come up smelling of roses

Carolyn Devlin writes about a hot ChemComm article for Chemistry World

A new perfume delivery system has been developed by chemists in the UK as a way of keeping sweet smells around for longer. This cleverly designed system tags fragrance alcohols – such as 2-phenylethanol, which has a rose-like scent – onto odourless ionic liquids. In the tagged form, the material has no smell. However, when it comes into contact with water, the link is broken and the fragrance is released – along with its sweet scent.

Fragrance alcohols are typically volatile, so their scent can be lost soon after a perfumed product is applied. A lot of research has been dedicated to finding ways to keep scents around for longer.


Read the full article in Chemistry World»

Read the original journal article in ChemComm:
Pro-fragrant ionic liquids with stable hemiacetal motifs: water-triggered release of fragrances
H. Q. Nimal Gunaratne, Peter Nockemann and Kenneth R. Seddon 
Chem. Commun., 2015,51, 4455-4457
DOI: 10.1039/C5CC00099H, Communication

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