Annual Scientific Report 2014

A concave compound self assembles thanks to reversible and controllable hydrogen bonding to form a dynamic capsule able to selectively extract fullerene derivatives of given size and shape. The process for the separation of fullerene derivatives is based on a sequential selective encapsulation in an appropriate solvent system of the fullerenes contained in a mixture. The capsule is formed by reversible self‐assembly of two concave fragments. The encapsulation of the fullerene derivative having the best fitting geometry for the cavity of the capsule is fast and selective.

A process for the direct cupration of fluoroform has been developed. This exceedingly simple process employs only cheap reagents and is advantageously run at room temperature to produce CuCF₃ reagents that are useful in trifluoromethylation reactions. Chemical compounds bearing a trifluoromethyl group are widely used in the production of various pharmaceuticals and agrochemicals as well as specialty materials, polymers, composites, building blocks, and intermediates for various needs. Fluoroform, CF₃H, is an ideal source of CF₃ because it is inexpensive, readily available in large industrial quantities, non‐toxic, and not an ozone depleter.

Chemical reduction of carbon dioxide to methanol and its derivatives (such as DME) is considered one of the key technologies to reduce both global warming and fossil fuels dependency. Unlike the currently used process for methanol synthesis, ICIQ’s process provides excellent conversions and selectivity to methanol in one pass through the reactor, thereby providing the highest time yield observed for the chemical reduction of CO₂.

SCIPIO is a software that allows to handle, store and manipulate output files from computational chemistry experiments. SCIPIO is a general data extractor and manager that is here presented as a Computational Chemistry Results Repository, which is a sort of tailored electronic notebook allowing for substructure searches and for the generation of “ready to publish” reports.

A highly active and stable heterogeneous catalyst consisting in ruthenium nanoparticles stabilized with phosphine ligands embedded into a solid support has been developed. Hydrogenation of aromatics can be operated under mild conditions and under solvent free conditions, thereby rendering the process more sustainable and easy to implement. The catalyst can also be recycled at least 10 times without significant loss of activity, which makes it attractive for continuous flow applications.

A nanoparticle containing two different populations of chromophores and funcionalized with a dye-labelled peptide sensitive to the action of a hydrolytic enzyme has been developed. In that way, the optical response of the system can directly be correlated, in a quantitative manner, to the activity of a specific enzyme found in the medium where the nanoparticle is placed, thereby allowing for enzyme quantification.  This technology was applied to cystic fibrosis, through the analysis of the trypsin amount of faeces samples. It was shown that this system could allow for the determination of patient’s phenotype, thus avoiding genetic testing.

A family of compounds able to form a network of rings interconnected by rods at the micro/nanoscopic scale through a self-assembly process has been developed. These compounds could successfully be incorporated into plastic materials in which the characteristic assembly is conserved. Within a polymer matrix containing carbon materials such as carbon nanotubes (composite material), the carbon particles aggregate around the self-assembled network, forming a network of dispersed and interconnected carbon materials, giving rise to e.g. lower percolation thresholds.

A process for the direct cupration of pentafluoroethane has been developed. This exceedingly simple process employs only cheap reagents and is advantageously run at room temperature to produce CuC2F5 reagents that are useful in pentafluoroethylation reactions. Chemical compounds bearing a pentafluoroethyl group are widely used in the production of various pharmaceuticals and agrochemicals as well as specialty materials, polymers, composites, building blocks, and intermediates for various needs. Pentafluoroethane, C2F5H, is an ideal source of C2F5 because it is inexpensive, readily available in large industrial quantities and non‐toxic.

3-indolylmethanamines, and more particularly their chiral derivatives, constitute a relevant family of compounds for the crop protection and pharmaceutical industries. The invention provides a polymer-supported organocatalysts that is highly active and selective for the preparation of such compounds by Friedel-Crafts reactions. Being supported on a polystyrene resin, the catalyst is easily recyclable by filtration and can be used under continuous flow conditions, making it suitable for process intensification and the preparation of libraries of chiral compounds.

Benzene is a highly toxic chemical, potentially carcinogen, for which it is necessary to control the exposure of workers and individuals to benzene, especially in industrial environments. The regulatory exposure limit of benzene is of 0.1 ppm during 8 hours or 1 ppm during 15 minutes. Therefore, it is important and necessary to dispose of quick, reliable and precise devices for the monitoring of said exposition of workers to benzene.  A new device and process allowing for selectively detecting trace amounts of benzene with high sensitivity and in continuous mode, using cheap materials has been developed. The electrochemical sensor is based on a selective molecular receptor of benzene self-assembled onto  gold nanoparticles attached to  carbon nanotubes forming an electrode.

PEM electrolysis of water is regarded as a promising solution for hydrogen production from renewable energies (e.g. wind and solar) and water. New materials are required to enhance the performance of such devices while diminishing its operation costs. The invention provides a catalyst based on carbon black and cobalt oxide nanoparticles, acting as a hydrogen evolution electrode with productivity similar or higher than platinum-based electrodes. This catalyst could substitute platinum in PEM cells.