Naphthalenediimides (NDIs) are versatile molecules that have been used in aqueous media in the assembly of catenanes and knots. In this talk we explore the dynamic combinatorial synthesis of [2]catenanes based on cysteine appended NDI (electron acceptor, A) and benzodithiophene (electron donor, D) cores. The chirality of the building blocks is of paramount importance in the aromatic stacking present in the resulting [2]catenanes; the L,L-building block pair leads to a DAAD stack while the L,D-pairing gives a DADD stack. This is the first example of a structural divergent reaction on racemic mixtures carried out under dynamic combinatorial conditions. We postulate that the differentiating factor between the two reacting enantiomers is the transient formation of the pseudorotaxane precursors leading to the [2]catenane products.

Structural divergent reactions on racemic mixtures: The dynamic combinatorial dimension

256th National Meeting (2018)

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