Switchable supramolecular helices for asymmetric stereodivergent catalysis.

Despite recent developments on the design of dynamic catalysts, none of them have been exploited for the in-situ control of multiple stereogenic centers in a single molecular scaffold. We report herein that it is possible to obtain in majority any amongst the four possible stereoisomers of an amino alcohol by means of a switchable asymmetric catalyst built on supramolecular helices. Hydrogen-bonded assemblies between a benzene-1,3,5-tricarboxamide (BTA) achiral phosphine ligand coordinated to copper and a chiral BTA comonomer are engaged in a copper-hydride catalyzed hydrosilylation and hydroamination cascade process.

STAACS3: Simulation Tool for AAC with Single-Switch Scanning.

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Rationalizing the Extent of the "Sergeants-and-Soldiers" Effect in Supramolecular Helical Catalysts: Effect of Copper Coordination.

Aggregation of supramolecular helices, for example through interdigitation of their alkyl side chains or through more directional supramolecular interactions, leads to hierarchical architectures with original structural and chiroptical properties. However, when a chiral monomer (the "sergeant") is introduced as a minor component in these assemblies composed of a majority of achiral monomers (the "soldiers"), it is not clear how the aggregation changes the ability of the sergeant to induce a preferential helicity to the polymer main chain (the so-called "sergeants-and-soldiers" effect). This study reports a detailed investigation of the influence of [Cu(OAc) ⋅H O] coordination on the structure and chiroptical properties of helical hydrogen-bonded co-assemblies composed of a catalytically-active benzene-1,3,5-tricarboxamide (BTA) monomer, acting as the "soldier", and an enantiopure BTA monomer derived from cyclohexylalanine, playing the role of the "sergeant".

Interplay Between Hydrogen Bonding and Electron Transfer in Mixed Valence Assemblies of Triarylamine Trisamides.

Hydrogen-bonding interactions are assumed to play a critical role in the long-range transport of light or charge recently observed in supramolecular assemblies of C -symmetrical discotic molecules. Herein, the structure of mixed valence assemblies formed by irradiating triarylamine trisamide (TATA) molecules was determined by multifarious techniques under various conditions with the aim of probing the interplay between the hydrogen bonding network and the rate of electron transport in different states (solution, gel, film). Irradiation was performed under initial states that vary by the degree of association of TATA monomers through hydrogen bonds.