Molecular Capsules from Resorcinol derived Calixarenes: Host-Guest Chemistry

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

In this Chem. Soc. Rev. review article, Kenji Kobayashi and Masamichi Yamanaka from Shizuoka University, Japan, give a detailed account of the host guest chemistry of a particular type of calixarene. Simple calixarenes are usually derived from, for example, a phenol and formaldehyde in an electrophilic aromatic substitution reaction. This yields a puckered basket structure containing a ring of methylene spaced phenols groups.

Calixarenes based on 1,3-dihydroxybenzene, also known as resorcinol (calix[4]resorcinarenes) are derived from similar chemistry and are described in this review. Capsule like materials containing covalently bound spacers between pairs of calix[4]resorcinarene units are briefly mentioned, while the majority of the review is devoted to capsules (or cavitands) containing substitutents capable of hydrogen bonding, metal coordination and other dynamic bonding, resulting in powerful, self-assembled host-guest interactions. The calix-[4]-resorcinarenes have extra rigidity in their structure, due to methylene bridging between the resorcinol oxygens of neighbouring units, with functional groups at the in-between 2-position.

Functionality introduced includes carboxylic acids, nitriles, halides, boronic acids, aldehdyes, alcohols and even a biypridyl unit. For example, a cavitand, containing phenol groups, not involved with other bonding, can be deprotonated to neatly bind pyrazine, in a hydrogen bound network, resulting in a dimeric self assembled cavitand.

Generic calix[4resorcinarene structures and a host-guest interaction with pyrazine]

Other examples are provided with mixed donors such as phenols and pyrdine groups in the same material. These heterodimeric cavitands can give access to a more advanced level of specificity, in these cases, for a variety of organic guests. Stronger bound capsule systems are described based on metal coordination. A nitrile substituted calix-[4]-resorcinarene and its palladium, platinum and counter-anion host-guest chemistry are briefly described, while examples self-assembled capsules with coordinating bipyridyl and dithiocarbamate units are also included.

The molecular and synthetic variety in this review is impressive. It is an enjoyable read, and should prove valuable to researchers in many disciplines. The application of such designed and potentially specific calix[4]resorcinarenes, and their mode of action in self-assembling and modifying guest reactivity is a  fascinating research area!

Read this Chem. Soc. Rev., Review Article today for free:

Self-assembled capsules based on tetrafunctionalized calix[4]resorcinarene cavitands
Kenji Kobayashi and Masamichi Yamanaka
DOI: 10.1039/C4CS00153B

*Access is free untill the 31.07.14 through a registered RSC account – click here to register

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Supramolecular Photochemistry Themed Issue

Chemical Society Reviews is delighted to present a themed issue on supramolecular photochemistry, dedicated to Professor Nick Turro, who sadly passed away in 2012. To celebrate Turro’s enormous contribution to photochemical sciences,  guest editor Alberto Credi has gathered together the most prominent, recent advances in photochemistry at its frontiers with supramolecular chemistry, materials science, and biochemistry.

To read the full collection, click on the link below:

Chemical Society Reviews, Issue 12, Supramolecular Photochemistry
Guest Editor: Alberto Credi

We hope you enjoy reading this collection as much as we did!

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New appointments to Chem Soc Rev Advisory Board

Chem Soc Rev is pleased to announce the appointment of seven new members to the Advisory Board

Elena Fernández
Professor Elena Fernández leads the Catalytic Organoborane Chemistry group at the University Rovira i Virgili in Spain. Her group’s research interests centre on the application of transition metal complexes for selective organic purposes. Professor Fernández received the National Award for Excellence of Research in Organometallic Chemistry in 2014.
Shigehiro Yamaguchi
Professor Shigehiro Yamaguchi is Principal Investigator of the Yamaguchi group at Nagoya University’s Institute of Transformative Bio-Molecules. He works on a variety of topics in the general fields of main group chemistry and physical organic chemistry.
Itaru Hamachi
Itaru Hamachi is a Professor at Kyoto University. His research interests include live-cell organic chemistry, chemical biology, bioorganic and bioinorganic chemistry, and supramolecular biomaterials. In 2014, Professor Hamachi was awarded the Nagoya Silver Medal, which is awarded every year to a ‘rising Japanese scientist whose research has had a major impact on the field of synthetic organic chemistry’.
Dave Adams
Dave Adams earned his PhD at the University of York and has since worked in both academia and industry. He joined the University of Liverpool in 2008, where his group designs novel structures and materials utilising the self-assembly of peptides, peptide-polymer conjugates and polymers.
Laurel Schafer
Laurel Schafer is a Professor at the University of British Columbia. Her group’s research bridges the areas of organometallic and organic chemistry, by preparing discrete early transition metal and lanthanide complexes for use in the atom-economic, catalytic synthesis of amines.
Stephen Withers
Professor Stephen Withers leads a group at the University of British Columbia’s Centre for High-Throughput Biology (ChiBi).  Their research focuses on enzymes involved in glycoside cleavage and synthesis, with special emphasis on their mechanisms. They also utilise their findings in the development of new applications, ranging from new enzyme-based synthetic methodologies to new therapeutics and imaging agents.
Peng Chen
Professor Peng Chen’s chemical biology group at Peking University focuses on protein chemistry and engineering. Professor Chen was the recipient of the 2014 Chem Soc Rev Emerging Investigator Award, in recognition of his significant contribution to the field of chemical biology.
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175 Faces of Chemistry – Sason Shaik

Chemical Society Reviews contributor Sason Shaik, who recently published “A tutorial for understanding chemical reactivity through the valence bond approach”, features in our “175 Faces of Chemistry project”. He speaks about “these creatures called orbitals”, and the time when his project destroyed all of his spatulas.

Read Sason’s story.

In the countdown to our 175th Anniversary, we are celebrating the achievements of 175 inspirational scientists. Find out more and be inspired.

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MOF2014: Poster abstract deadline 30 June

4th International Conference on Metal-Organic Frameworks & Open Framework Compounds

MOF2014
28 September – 1 October 2014, Kobe, Japan

Deadline of poster abstract submission: 30 June

Our forthcoming Chem Soc Rev themed issue on Metal Organic Frameworks will be promoted at the forthcoming MOF2014 Conference, with all delegates receiving a free USB flash drive with a copy of the whole MOFs themed issue. The guest editors are Susumu Kitagawa (Kyoto University), Chair of MOF2014, and (Joe Zhou, Texas A&M University).

Keynote Speakers:
Xiao-Ming Chen, Sun-Yat-Sen University/PRC
Andrew Cooper, University of Liverpool/UK
Roland Fischer, Ruhr-University Bochum/Ger
Jeffrey Long, University of California, Berkeley/USA
George Shimizu, University of Calgary/Can
Myunghyun Paik Suh, Seoul National University/RoK
Qiang Xu, National Institute of Advanced Industrial Science and Technology (AIST)/Jpn
Omar Yaghi, University of California, Berkeley/USA

Submit your poster abstract for MOF2014

Preview Chem Soc Rev themed issue on Metal Organic Frameworks

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Douglas Stephen is awarded Chemical Institute of Canada Medal

Congratulations to our Associate Editor Douglas Stephan who is the 2014 winner of the Chemical Institute of Canada Medal – the CIC’s top award!

Doug was awarded this medal for his outstanding contribution to the science of chemistry in Canada. Professor at the University of Toronto and author of over 350 articles and 75 patents, Doug’s research exploits fundamental studies to target innovative new technologies for the efficient production of  desirable chemical products.

This year Doug won the Applied Catalysis Award, joining the group of 2014 RSC Award Winners.

Click on the links below to view some of Doug’s latest papers:

Max M. Hansmann, Rebecca L. Melen, Frank Rominger, A. Stephen K. Hashmi and Douglas W. Stephan
Chem. Commun., 2014,50, 7243-7245
DOI: 10.1039/C4CC01370K, Communication

Phosphine catalyzed reduction of CO2 with boranes

Tongen Wang and Douglas W. Stephan
Chem. Commun., 2014,50, 7007-7010
DOI: 10.1039/C4CC02103G, Communication
You can view more of Douglas’ research on his author archive on our publish platform – we hope you enjoy reading his work as much as we do!
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Positioning Metal Organic Frameworks

Surface functionalization by microcontact printing

Metal organic frameworks (MOFs) are remarkable materials which have great potential for different applications where an accessible surface area is a critical feature. However, the ability to control the position of MOFs is also crucial for their use in many devices. Paolo Falcaro et al from the CSIRO, Australia present a review on the current technologies that enable precise positioning of MOFs onto different platforms.

To access the full review for free* click the link below:

MOF positioning technology and device fabrication
Paolo FalcaroRaffaele RiccoCara M. DohertyKang LiangAnita J. Hill and Mark J. Styles
DOI: 10.1039/C4CS00089G

Similar reviews can be found in our metal organic frameworks themed collection.

*Access is free until 20th June through a registered RSC account – click here to register

Not only does this review demonstrate examples of devices in which the control of MOF position and functionalization will play a major technological role, but the authors have also provided video material clearly demonstrating the various techniques. The growth of MOFs can be controlled on different substrate with the intention of providing protocols suitable for MOF-based device fabrication. Watch the video’s  for demonstrations of each technique. The full collection of videos can be viewed on our related content page.

2) Gel-Layer approach

Gel-Layer approach

3) Electrochemical method proposed by Ameloot et al

Electrochemical method proposed by Ameloot et al

4) The formation of crystals within confined columns

The formation of crystals within confined columns

5) Patterns produced by direct conversion from zinc oxide precursor films.

Patterns produced by direct conversion from zinc oxide precursor films

6) Inkjet printing

Inkjet printing

7) Spray coating

Spray coating

Photolithography technique

Photolithography technique

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Chem Soc Rev Chair wins the Supramolecular Chemistry Award

Philip Gale, chair of the Chem Soc Rev Editorial Board, has won the 2014 Supramolecular Chemistry Award for his outstanding body of work on small organic molecules containing hydrogen bond donor arrays for selective guest complexation, and the design and study of minimalist anion transporters.

Supramolecular Chemistry Award 2014 WinnerPhil was delighted to receive this award from the Royal Society of Chemistry. “My group is working to find new ways of treating cancer and cystic fibrosis using anion transporters and I am delighted that the hard work and dedication of my students and post-docs has been recognised in this way,” he says.

We would like to congratulate Phil on this achievement and take this opportunity to thank him for his excellent contributions towards the Royal Society of Chemistry’s flagship reviews journal, Chem Soc Rev which continues to publish high-impact, succinct and reader-friendly articles at the forefront of the chemical sciences.

Phil’s research paper, published in Chemical Science earlier this year , describes a new design principle for transmembrane anion carrier and is free* to access, so click the link below to download it in full.

Lipophilic balance – a new design principle for transmembrane anion carriers
Hennie Valkenier, Cally J. E. Haynes, Julie Herniman, Philip A. Gale and Anthony P. Davis
DOI: 10.1039/C3SC52962B

Phil has published several papers in RSC Journals this year including his most recent communication in Chem Comm on the tripodal molecules for the promotion of phosphoester hydrolysis. Many of his papers are free to download as they have been published via open access, you can visit his author archive to view the full collection.

All articles in the dedicated themed collection of papers celebrating the 2014 RSC Prize and Award winners are free* to access until 6th June.

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

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Nanoplasmonics

Chem Soc Rev presents a nanoplasmonics themed issue and a nanoplasmonics Faraday Discussion.

Our current Chem Soc Rev issue is a themed issue on nanoplasmonics, guest edited by Luis Liz-Marzan, Catherine Murphy and Jianfang Wang.

Nanoplasmonics concerns light-matter interactions with nanoscale materials.  Advances in fabrication, computation, and applications ranging from biomedicine to energy have burgeoned in the last 5 years. This themed issue gathers together a variety of reviews and tutorial reviews covering all chemical aspects of the field, from synthesis and fabrication to plasmon-enhanced effects in physical and biological systems.

To read the full editorial for free, click the link below:

Nanoplasmonics
Luis M. Liz-Marzán, Catherine J. Murphy and Jianfang Wang
DOI: 10.1039/C4CS90026J

If you are interested in Nanoplasmonics, why not register for the Faraday Discussion in London, February 2015.

This meeting aims to highlight the most recent breakthroughs in the multidisciplinary field of nanoplasmonics. The following themes will be covered:

  • Plasmonic nanoparticles and metamaterials with designed optical properties
  • Surface plasmon enhanced spectroscopies
  • Quantum plasmonics, gain and spasers
  • Biosensing and biomedical applications of plasmonics

Faraday Discussions have a special format where research papers written by the speakers are distributed to all participants before the meeting, and most of the meeting is devoted to discussing the papers. Click the link to find out more about the Nanoplasmonics Faraday Discussion.

The oral abstract deadline is Monday 19th May 2014 – so don’t delay submit your oral abstract today! You can view details of the other submission deadlines on the Abstract Submission homepage.

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Stephen Goldup and Douglas Stephan win 2014 RSC Awards

Please join us in congratulating two of our very own board members on their achievements this year:

Hickinbottom Award

Stephen Goldup

Chem Soc Rev Advisory Board member Stephen Goldup has won the Hickinbottom Award for pioneering work on rotaxane synthesis and the formation of mechanically bonded systems.

Stephen’s latest article is part of the ‘Celebrating the 2014 RCS Prize and Award Winners’ themed collection and is free* to access for a limited time only.

Chemical consequences of mechanical bonding in catenanes and rotaxanes: isomerism, modification, catalysis and molecular machines for synthesis
Edward A. Neal and   Stephen M. Goldup
Chem. Commun., 2014,50, 5128-5142
DOI: 10.1039/C3CC47842D

Applied Catalysis Award

Douglas Stephan

Chem Soc Rev Associate Editor Douglas Stephan has won the Applied Catalysis Award for the development of new commercially viable, transition-metal based and metal-free catalyst technologies for polymerization, hydrogenation and metathesis.

To celebrate Douglas’ achievement, his latest publication is free* to access for a limited time only.

Frustrated Lewis pair chemistry of carbon, nitrogen and sulfur oxides
Douglas W. Stephan and Gerhard Erker
Chem. Sci., 2014, Advance Article
DOI: 10.1039/C4SC00395K

You can access papers by other 2014 RSC Prize and Award Winners for free* for a limited time. A full list of winners and more information about RSC Prizes and Awards can be found at: www.rsc.org/awards.

*Access is free until 06.06.14 through a registered RSC account – click here to register

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