Autoresolution of Segregated and Mixed p-n Stacks by Stereoselective Supramolecular Polymerization in Solution

A chirality driven self-sorting strategy is introduced for the controlled supramolecular organization of donor (D) and acceptor (A) molecules in multicomponent assemblies. The trans-1,2-bis(amido)cyclohexane (trans-BAC) has been identified as a supramolecular motif with strong homochiral recognition to direct this chirality controlled assembly process of enantiomers in solution. Stereoselective supramolecular polymerization of trans-BAC appended naphthalene diimide monomers (NDIs) has been probed in detail by spectroscopic and mechanistic investigations. This chirality-driven self-sorting design of enantiomeric components also offers to realize mixed and segregated D-A stacks by supramolecular co-assembly of the NDI acceptors with trans-BAC appended dialkoxynaphthalene (DAN) donor monomers. Such an unprecedented chirality control on D-A organization paves the way for the creation of supramolecular p-n nanostructures with controlled molecular-level organization.