Preparations of spherical nanoparticles of chiral Cinchona alkaloid-based bridged silsesquioxanes and their use in heterogeneous catalysis of enantioselective reactions.

Two spherical nanoparticulate materials were prepared by base-catalyzed sol-gel hydrolysis/self-condensation of the bis-Cinchona alkaloid-phthalazine-based bridged bis(triethoxysilanes). For the purpose of comparing the catalytic properties, two compact materials were also prepared from the same precursors using a fluoride-catalyzed sol-gel process. All materials were characterized by SEM, TEM, solid-state 29Si NMR and 13C NMR, TGA, and FTIR. The prepared silsesquioxane-based materials were studied as potential heterogeneous catalysts for selected enantioselective reactions. The spherical material with regularly incorporated bis-quinine-phthalazine chiral units exhibited good to excellent enantioselectivities in osmium-catalyzed dihydroxylations of alkenes. Enantioselectivities observed in dihydroxylations of aromatic trans-alkenes were as excellent as those observed with the homogeneous catalyst (DHQ)2-PHAL. One compact and one nanoparticulate material was successfully recycled and reused five times without loss of enantioselectivity. Furthermore, both quinine-based and cinchonine-based materials were tested as heterogeneous organocatalysts for chlorolactonization of 4-arylpent-4-enoic acids. The materials showed only moderate enantioselectivities; however, these are the first heterogeneous catalysts for enantioselective chlorolactonization published so far.

(1S,2S)-Cyclohexane-1,2-diamine-based Organosilane Fibres as a Powerful Tool Against Pathogenic Bacteria.

An urgent need to find an effective solution to bacterial resistance is pushing worldwide research for highly effective means against this threat. Newly prepared hybrid organosilane fibres consisting of a (1S,2S)-cyclohexane-1,2-diamine derivative, interconnected in the fibre network via covalent bonds, were fully characterised via different techniques, including FTIR, TGA-FTIR, SEM-EDS, and solid-state NMR. Fibrous samples were successfully tested against two types of pathogenic bacterial strains, namely Staphylococcus aureus, and Pseudomonas aeruginosa. The obtained results, showing >99.9% inhibition against Staphylococcus aureus and Pseudomonas aeruginosa in direct contact compared to the control, may help particularly in case of infections, where there is an urgent need to treat the infection in direct contact. From this point of view, the above-mentioned fibrous material may find application in wound healing. Moreover, this new material has a positive impact on fibroblasts viability.