What is it about?
A new synthetic method has been developed for the formation of a molecule representing the olympic rings, as well as related compounds. Molecular imaging of the reaction products with scanning tunnelling microscopy (STM) and non-contact atomic force microscopy (NC-AFM) characterised the 6H-benzo[cd]pyrene and other related compounds.
Featured Image
Photo by Kyle Dias on Unsplash
Why is it important?
This work highlights the growing capabilities of single molecule microscopy techniques as applied to a polyaromatic hydrocarbon and non-Kekulé fragment of graphene.
Perspectives
Imagine synthesizing a chemical that looks like the Olympic rings and then looking at INDIVIDUAL molecules of that compound under a microscope! That's what this work achieved. We hypothesized a compound that looked like the rings, registered it on ChemSpider with the name Olympicence, and then engaged with scientists at University of Warwick to make the molecule and scientists at IBM-Zurich to perform the microscopy. The resulting work created a LOT of media coverage! What a wonderful collaboration on some fun science that has since catalyzed research into the chemical. For me this was an example of the power of distributed teams but that ended up catalyzing some interesting science, especially judging by the number of publications that came out of the work. Because the synthesis was Open, and all data sharing was open, there were publications about Olympicene already published BEFORE we published this article.
Dr Antony John Williams
United States Environmental Protection Agency
Read the Original
This page is a summary of: The Synthesis and STM/AFM Imaging of ‘Olympicene’ Benzo[cd]pyrenes, Chemistry - A European Journal, December 2014, Wiley,
DOI: 10.1002/chem.201404877.
You can read the full text:
Resources
In Celebration of Chemistry in Sports. Introducing Olympicene.
The initial introduction to the Olympicene project as announced on the ChemConnector website
Olympicene on ChemSpider
The ChemSpider record for Olympicene with the initial structure registered and related data including proton NMR spectrum.
Photo finish for Olympicene in Chemistry World
Chemistry World article about olympicene "UK chemists have synthesised and imaged a molecule that closely resembles the Olympic rings. While the molecule shows promise for applications in electronics, the project was undertaken principally as a means to celebrate the Olympics coming to London in 2012, as well as encouraging online sharing of synthetic chemistry procedures."
Olympicene on the Chemistry Periodic Table of Videos
Olympicene is a gimmicky but clever molecule based on a famous set of rings - yet they are not linked!!! A discussion with Martin Poliakoff in a video.
The Story of Olympicene from Concept to Completion on the ChemConnector blog
The story of Olympicene, and our intention to try and get it synthesized and analyzed, was first reported in August 2011. 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. This blog post summarizes the project.
Stunning image of smallest possible five rings
Press release from the University of Warwick
Gold medal! Scientists create smallest-ever version of Olympics logo - a single molecule with five familiar 'rings'
A story by the Daily Mail about Olympicene
An entry about olympicene in Wiktionary
How many compounds get an entry in the Wiktionary???
Theoretical Prediction of the Structures and Energies of Olympicene and its Isomers
This paper offers the first theoretical study of the kinetic stability of olympicene and its isomers. We use the parametric two-electron reduced density matrix (2-RDM) method, which takes the 2-RDM as the basic variable in lieu of the traditional wave function in calculations . Our calculations demonstrate that olympicene’s isomers may be separated into aromatic and diradical isomers. The olympicene molecule has the potential to complement pentacene as an organic semiconductor.
Olympicene's "Top Secret" Final Step
Bog post from "Just Like Cooking" about the final synthetic step.
Effect of van der Waals Interactions on the Adsorption of Olympicene Radical on Cu(111): Characteristics of Weak Physisorption versus Strong Chemisorption
The authors report on the results of Olympicene radical (C19H11) adsorption characteristics on Cu(111) obtained within the density functional framework with and without the inclusion of self-consistent van der Waals (vdW) interactions to evaluate their effects. Theircalculations suggest that the vdW interactions enhance the adsorption energies, and the degree of enhancement strongly depends on the implementation.
Structures and Electronic Properties of Heavier Congeners of Disk-Like Molecules: (Si, Ge) Sulflower and (Si, Ge) Olympicene
The ground-state structures, HOMO–LUMO gaps, singlet–triplet splitting, and the UV–vis absorption spectra for Si, Ge-substituted analogues of the recently synthesized disk-like π-conjugated molecules, like octathio[8]circulene, popularly termed “sulflower”, and 2H-benzo[cd]pyrene, popularly termed “olympicene”, are studied using density functional theory.
ARTICLE: Functionalized olympicene (C19H12) as anode material for Li-ion batteries: a DFT approach
density functional theory calculations were carried out to investigate the potential application of bare and functionalized olympicene molecules (C19H12) as anode materials for Li-ion batteries. The interactions of Li and Li+ were studied with these molecules and the cell voltages were calculated. The results reveal that the cell voltage of this molecule is greater than some well-known carbon based materials such as C32, C60, C70 fullerenes and carbon nanotubes.
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