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The Story of Olympicene from Concept to Completion

27 May

The story of Olympicene, and our intention to try and get it synthesized and analyzed, was first reported in August 2011 here. The original conversation was between Prof Graham Richards and I over a drink in Belgium at the RSC Editors Symposium in March 2010. The concept of having someone synthesize a small organic molecule that would be a molecular representation of a famous symbol of sport was a fascinating challenge. And, always one for a challenge, it was one that was pursued with great gusto!

Since we had started the ChemSpider SyntheticPages (CSSP) platform recently I thought it was appropriate to kick off a grand vision discussion with Peter Scott, one of the editors of CSSP. My original idea that I bounced off of Peter was a big one…an international competition exposed to the chemistry community. Encourage chemistry labs around the world to submit their step-by-step syntheses to CSSP. We would be able to collect and expose all of this work to the entire chemistry community. We would set up a voting scheme for the community to give their input on what was the most elegant synthesis, the greenest, what had the best analytical data, what had the best write up. Not all categories were detailed at that time and would come later but the concept of bronze, silver and gold medal winners in an international chemistry competition made sense. We were really excited by the possibilities but for many reasons (read that as many distractions) we rolled the announcement out as a smaller announcement and encouraged participation as best as we could with a small engagement profile via this blog. It did seem to garner a lot of attention but as is common with such projects the participation was not as high as we expected. Nevertheless one lab did step up to participate in the project, the lab of David Fox Group at the University of Warwick. David is a colleague of Peter Scott’s…small world…

David had one of his students pursue the synthesis, not only because the olympicene molecule might be an elegant piece of synthetic work, but also because some of the envisaged properties could well be of value (more on that later!). Anish started publishing his syntheses to CSSP in November of last year as listed here. You can see the Olympicene compound coming together step by step and yes, the final step is not yet reported! Once the compound was made then the possibilities of having it analyzed seemed rather interesting, especially having seen the work reported by IBM in 2009 regarding the single molecule imaging of pentacene. Also, I had followed the work of Marcel Jaspars, who I had known during my time working at ACD/Labs when I was working on Computer-Assisted Structure Elucidation [1,2]. Marcel had recently worked on an NMR and microscopy imaging project to confirm a chemical compound structure. Again, small world. I asked Marcel for an intro to the researchers at IBM and we started a dialogue. Researchers at University of Warwick had already applied Scanning Tunnelling Microscopy (Dr Giovanni Costantini and Ben Moreton at Warwick) and they then connected with Leo Gross with the idea of using the noncontact atomic force microscopy approach.

Within a fairly short period of time IBM had performed the very elegant work of imaging olympicene…just one of the images is shown below but there are others shown on the Flickr account.

A single olympicene molecule is just 1.2 nanometres in width, about 100,000 times thinner than a human hair. This is beautiful! For whatever reason it looks like a molecule with a smile at the success of the work too!

The story of the work is described in this video below.

The work is not over yet! There is a research paper to come from the University of Warwick and IBM Research labs as there is definitely unique science that has come out of this work and definitely needs to be reported. That molecule, as it were, is “NOT just a pretty face”. We will submit all the appropriate images and available analytical data onto ChemSpider and CSSP as time allows.

For now I simply smile at the story of a concept discussion between Graham and I that was taken into the hands of superb scientists and brought to fruition. Congratulations to ALL of those who worked on the project in David Fox’s and Leo Gross’s labs. Thanks to the marketing people at IBM, RSC and Warwick for bringing together all of the materials in a tight time frame to tell the story. My thanks to my colleagues at RSC who believed in the potential of this project and especially to Peter Scott for seeing the potential and willingly participating! This project is a great example of international collaboration and pushing science to its extremes. It was a pleasure to be involved if only at a concept level and HOPEFULLY I will get to meet the scientists who did the work sometime!

 

About tony

Antony (Tony) J. Williams received his BSc in 1985 from the University of Liverpool (UK) and PhD in 1988 from the University of London (UK). His PhD research interests were in studying the effects of high pressure on molecular motions within lubricant related systems using Nuclear Magnetic Resonance. He moved to Ottawa, Canada to work for the National Research Council performing fundamental research on the electron paramagnetic resonance of radicals trapped in single crystals. Following his postdoctoral position he became the NMR Facility Manager for Ottawa University. Tony joined the Eastman Kodak Company in Rochester, New York as their NMR Technology Leader. He led the laboratory to develop quality control across multiple spectroscopy labs and helped establish walk-up laboratories providing NMR, LC-MS and other forms of spectroscopy to hundreds of chemists across multiple sites. This included the delivery of spectroscopic data to the desktop, automated processing and his initial interests in computer-assisted structure elucidation (CASE) systems. He also worked with a team to develop the worlds’ first web-based LIMS system, WIMS, capable of allowing chemical structure searching and spectral display. With his developing cheminformatic skills and passion for data management he left corporate America to join a small start-up company working out of Toronto, Canada. He joined ACD/Labs as their NMR Product Manager and various roles, including Chief Science Officer, during his 10 years with the company. His responsibilities included managing over 50 products at one time prior to developing a product management team, managing sales, marketing, technical support and technical services. ACD/Labs was one of Canada’s Fast 50 Tech Companies, and Forbes Fast 500 companies in 2001. His primary passions during his tenure with ACD/Labs was the continued adoption of web-based technologies and developing automated structure verification and elucidation platforms. While at ACD/Labs he suggested the possibility of developing a public resource for chemists attempting to integrate internet available chemical data. He finally pursued this vision with some close friends as a hobby project in the evenings and the result was the ChemSpider database (www.chemspider.com). Even while running out of a basement on hand built servers the website developed a large community following that eventually culminated in the acquisition of the website by the Royal Society of Chemistry (RSC) based in Cambridge, United Kingdom. Tony joined the organization, together with some of the other ChemSpider team, and became their Vice President of Strategic Development. At RSC he continued to develop cheminformatics tools, specifically ChemSpider, and was the technical lead for the chemistry aspects of the Open PHACTS project (http://www.openphacts.org), a project focused on the delivery of open data, open source and open systems to support the pharmaceutical sciences. He was also the technical lead for the UK National Chemical Database Service (http://cds.rsc.org/) and the RSC lead for the PharmaSea project (http://www.pharma-sea.eu/) attempting to identify novel natural products from the ocean. He left RSC in 2015 to become a Computational Chemist in the National Center of Computational Toxicology at the Environmental Protection Agency where he is bringing his skills to bear working with a team on the delivery of a new software architecture for the management and delivery of data, algorithms and visualization tools. The “Chemistry Dashboard” was released on April 1st, no fooling, at https://comptox.epa.gov, and provides access to over 700,000 chemicals, experimental and predicted properties and a developing link network to support the environmental sciences. Tony remains passionate about computer-assisted structure elucidation and verification approaches and continues to publish in this area. He is also passionate about teaching scientists to benefit from the developing array of social networking tools for scientists and is known as the ChemConnector on the networks. Over the years he has had adjunct roles at a number of institutions and presently enjoys working with scientists at both UNC Chapel Hill and NC State University. He is widely published with over 200 papers and book chapters and was the recipient of the Jim Gray Award for eScience in 2012. In 2016 he was awarded the North Carolina ACS Distinguished Speaker Award.

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8 Responses to The Story of Olympicene from Concept to Completion

  1. tony

    May 27, 2012 at 11:14 pm

    As David Fox comments in this EurekAlert: http://www.eurekalert.org/pub_releases/2012-05/uow-sio052412.php

    “Alongside the scientific challenge involved in creating olympicene in a laboratory, there’s some serious practical reasons for working with molecules like this,” said Dr Fox.

    “The compound is related to single-layer graphite, also known as graphene, and is one of a number of related compounds which potentially have interesting electronic and optical properties.

     
  2. Gary Martin

    May 28, 2012 at 5:51 am

    An obvious elegant piece of work… isn’t it amazing what the chemical community can do when great minds are focused?

     
  3. John Fetzer

    May 30, 2012 at 5:01 pm

    This synthesis is a redoing,maybe withimprovements, of various work done over the past 75 years. The benzo[cd]pyrene is a free-radical compound that is not inherently stable, so the reduced dihydro-version is what can be isolated. The first reference toit was: Vollman, H.; Becker, H.; Correll, M.; Streeck, H.; Langbein, G., Pyrene and Its Derivatives, Justus Liebigs Ann. Chem., 1937, 531, 1-159. [all data]. Erich Clar did a lot of work in the 1960s with it, trying tomake large polycyclic aromatic hydrocarbons withit as the intermediate, two reacting with each other to fuse.

     
  4. James Demers

    February 9, 2013 at 10:04 pm

    The corresponging cation (olympiconium?) should be aromatic and nicely planar. I’m wondering what you get when you treat the material with a hydride abstracting agent, like Ph3C+ PF6-.

     

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