Rezultati na UKF projektu
Vjekoslav Štrukil, László Fábián, David G. Reid, Melinda J. Duer, Graham J. Jackson, Mirjana Eckert-Maksić i Tomislav Friščić
Towards an environmentally-friendly laboratory: dimensionality and reactivity in the mechanosynthesis of metal–organic compounds
We present a proof-of-principle study of an environmentally-friendly approach to laboratory research, in which the synthesis and structural characterisation of metal–organic complexes and frameworks are achieved without using bulk solvents; our study addresses the use of heteroditopic ligands for manipulating the dimensionality of metal–organic materials and describes how kinetic obstacles in such mechanosynthesis can be overcome.
Štrukil, Vjekoslav; Igrc, Marina Diana; Eckert-Maksić, Mirjana; Friščić, Tomislav
Click mechanochemistry: quantitative synthesis of "ready to use" chiral organocatalysts by efficient two-fold thiourea coupling on vicinal diamines
Mechanochemical methods of neat grinding and liquid-assisted grinding have been applied for the synthesis of mono- and bis-thioureas using the click coupling of aromatic and aliphatic diamines with aromatic isothiocyanates. The ability to modify the reaction conditions allowed the optimization of each reaction, leading to the quantitative formation of chiral bis-thioureas with known uses as organocatalysts or anion sensors.
Štrukil, Vjekoslav; Igrc, Marina Diana; Eckert-Maksić, Mirjana; Childs, S. L.; Reid, David G.; Duer, Melinda J.; Halasz, Ivan; Mottillo, C.; Friščić, Tomislav
A model for a solvent-free synthetic organic research laboratory: click-mechanosynthesis and structural characterization of thioureas without bulk solvents
The mechanochemical click coupling of isocyanates and amines has been used as a model reaction to demonstrate that the concept of a solvent-free research laboratory, in which the use of bulk solvents for either chemical synthesis or structural characterization, is applicable to the synthesis of small organic molecules. Whereas the click coupling is achieved in high yields by simple manual grinding of reactants, the use of an electrical, digitally controllable laboratory mill provides a rapid, quantitative and general route to symmetrical and non-symmetrical aromatic or aromatic-aliphatic thioureas. The enhanced efficiency of electrical ball milling techniques, such as neat grinding or liquid-assisted grinding, over manual mortar-and-pestle synthesis is demonstrated throughout the synthesis of 49 different thiourea derivatives. Comparison of powder X-ray diffraction data of mechanochemical products with structural information found in the Cambridge Structural Database (CSD), or obtained herein through single crystal X-ray diffraction, indicates that the mechanochemically obtained thiourea derivatives are pure in chemical sense, but can also demonstrate purity in a supramolecular sense, i.e. in all structurally explored cases the product consisted of a single polymorph. As an extension of our previous work on solvent-free synthesis of coordination polymers, it is now demonstrated that such polymorphic and chemical purity of selected thiourea derivatives, the latter being evidenced through quantitative reaction yields, can enable the immediate solvent-free structural characterization through powder X-ray diffraction aided by solid-state NMR spectroscopy
Štrukil, Vjekoslav; Margetić, Davor; Igrc, Marina Diana; Eckert-Maksić, Mirjana; Friščić, Tomislav
Desymmetrisation of aromatic diamines and synthesis of non-symmetrical thiourea derivatives by click-mechanochemistry
Ortho- and para-phenylenediamine were desymmetrised and quantitatively transformed into mono- and bis-(thio)ureas or mixed thiourea/ureas through a one-pot mechanochemical click reaction sequence ; mechanochemical desymmetrisation proceeds quantitatively without excess reagents and allows the controlled extension of a molecular structure by combining normally competing reactions.
Radovi prihvaćeni za objavljivanje:
Friščić, Tomislav; Halasz, Ivan; Štrukil, Vjekoslav; Eckert-Maksić, Mirjana; Dinnebier, Robert E.
Clean and efficient synthesis using mechanochemistry: coordination polymers, open metal-organic frameworks and metallodrugs
This review briefly discusses recent advances and future prospects in the mechanochemical synthesis of coordination compounds by ball milling and grinding, and highlights our contributions to the mechanosynthesis of porous metal-organic frameworks (MOFs) and zeolitic imidazolate frameworks (ZIFs), metal-organic pharmaceutical derivatives and metallodrugs using the recently developed mechanochemical methods of liquid-assisted grinding (LAG) and ion- and liquid-assisted grinding (ILAG).
Sudjelovanje na konferencijama
Kolokvij Zavoda za OKB i Sekcije za organsku kemiju HKD-a