A modular autonomous flow reactor combining monitoring technologies with a feedback algorithm is presented for the synthesis of the natural product carpanone. The autonomous self-optimizing system, controlled via MATLAB, was designed as a flexible platform enabling an adaptation of the experimental setup to the specificity of the chemical transformation to be optimized. The reaction monitoring uses either online high pressure liquid chromatography (HPLC) or in-line benchtop nuclear magnetic resonance (NMR) spectroscopy. The custom-made optimization algorithm derived from the Nelder-Mead and golden section search methods performs constrained optimizations of black-box functions in a multidimensional search domain, thereby assuming no a priori knowledge of the chemical reactions. This autonomous self-optimizing system allowed fast and efficient optimizations of the chemical steps leading to carpanone. This contribution is the first example of a multistep synthesis where all discrete steps were optimized with an autonomous flow reactor.
C 60 fullerene derivates bearing aliphatic chains can self-assemble into versatile supramolecular structures. Crosslinking of such self-assembled morphologies is an attractive approach to enhance the structural stability of these self-organized structures. We describe the synthesis of a C 60 functionalized with a single alkyl-chain bearing a diacetylene moiety. In a thin film, the molecule self-assembles into lamellar arrays. The character of the side-chain attached to the fullerene is key to the observed packing ability. The stabilization proceeds through solid-state polymerization of the diacetylene moieties. By blending the fullerene derivate with a cyanine dye, various nanostructured fullerene morphologies are obtained that can be selectively stabilized by thermal polymerization. These films can serve as basis for nanostructured fullerene scaffolds that can find applications in optics and electronics.
Described herein is a continuous‐flow strategy for the palladium‐catalyzed direct C−H arylation of indole‐3‐acetic acid derivatives with arenediazonium salts. A fully autonomous self‐optimizing flow platform was used to efficiently optimize the coupling reaction in a three‐dimensional space. The flow methodology developed is experimentally simple, mild, broad in scope, and safer than traditional batch approaches. Our continuous‐flow approach is particularly convenient to prepare precursors of pharmaceutically relevant compounds.
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