It is shown that corannulene-based strained psurfaces can be obtained through the use of mechanochemical Suzuki and Scholl reactions.B esides being solvent-free,t he mechanochemical synthesis is high-yielding,fast, and scalable. Therefore,gram-scale preparation can be carried out in afacile and sustainable manner.The synthesized nanographene structure carries positive (bowl-like) and negative (saddle-like) Gaussian curvatures and adopts an overall quasi-monkey saddle-type of geometry.Interms of properties,the non-planar surface exhibits ah igh electron affinity that was measured by cyclic voltammetry,w ith electrolysis and in situ UV/vis spectroscopye xperiments indicating that the one-electron reduced state displays al ong lifetime in solution. Overall, these results indicate the future potential of mechanochemistry in accessing synthetically challenging and functional curved p-systems. Scheme 1. Synthesis of curved p-systems.
The transformation of planar aromatic molecules into π-extended non-planar structures is a challenging task and has not been realized by mechanochemistry before. Here we report that mechanochemical forces can successfully transform a planar polyarene into a curved geometry by creating new C-C bonds along the rim of the molecular structure. In doing so, mechanochemistry does not require inert conditions or organic solvents and provide better yields within shorter reaction times. This is illustrated in a 20-minute synthesis of corannulene, a fragment of fullerene C60, in 66% yield through ball milling of planar tetrabromomethylfluoranthene precursor under ambient conditions. Traditional solution and gas-phase synthetic pathways do not compete with the practicality and efficiency offered by the mechanochemical synthesis, which now opens up a new reaction space for inducing curvature at a molecular level.
Resonant Acoustic Mixing (RAM) offers a simple, efficient route for mechanochemical synthesis in the absence of milling media or bulk solvents. Here, we show the use of RAM to conduct...
We present SpeedMixing, a rapid blending technology, as an approach for fast mechanosynthesis and discovery of model pharmaceutical cocrystals through rapid spinning in the absence of bulk solvents and milling/grinding media. Syntheses of pharmaceutical cocrystals based on the active pharmaceutical ingredients (APIs) carbamazepine, dihydrocarbamazepine, and nicotinamide demonstrate SpeedMixing as a method for rapid, scalable, as well as controllable and selective synthesis of cocrystals, cocrystal polymorphs and stoichiomorphs, including the discovery of an unexpected methanol solvate of the archetypal cocrystal of carbamazepine and saccharin, which has eluded extensive screens over 20 years.
It is shown that corannulene-based strained psurfaces can be obtained through the use of mechanochemical Suzuki and Scholl reactions.B esides being solvent-free,t he mechanochemical synthesis is high-yielding,fast, and scalable. Therefore,gram-scale preparation can be carried out in afacile and sustainable manner.The synthesized nanographene structure carries positive (bowl-like) and negative (saddle-like) Gaussian curvatures and adopts an overall quasi-monkey saddle-type of geometry.Interms of properties,the non-planar surface exhibits ah igh electron affinity that was measured by cyclic voltammetry,w ith electrolysis and in situ UV/vis spectroscopye xperiments indicating that the one-electron reduced state displays al ong lifetime in solution. Overall, these results indicate the future potential of mechanochemistry in accessing synthetically challenging and functional curved p-systems. Scheme 1. Synthesis of curved p-systems.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.