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Construction of Various Supramolecular Assemblies from Rod-Coil Molecules Containing Biphenyl and Anthracene Groups Driven by Donor-Acceptor Interactions.

Rod-coil amphiphilic functional molecules, comprising a rigid aromatic building block and hydrophilic oligoether dendrons as the coil segments, were synthesized. These compounds exhibit a powerful self-organizing ability to form supramolecular nanoparticles and long nanofibers in tetrahydrofuran/water solution, by controlling the intermolecular interaction of the rigid blocks. These molecules are able to form supramolecular polymers and, subsequently, to form sheetlike nanoaggregates, through charge-transfer interactions by the addition of a guest molecule, tetracyanoquinodimethane. Notably, upon addition of water-soluble 2,4,6-trinitrophenol, the self-assembly of these molecules exhibits the antagonistic effect owing to donor-acceptor and hydrophobic-hydrophilic interactions among the molecules. The experimental results reveal that various morphologies of rod-coil molecular assemblies can be obtained by tuning the molecular interaction and the hydrophilicity of guest electron-acceptor molecules. Interestingly, the cross-coupling reaction between phenylboronic acid and chlorobenzene occurs within the charge complexes of these molecular aggregates. This occurs in the nanoenvironment that affords an extremely concentrated reaction zone and reduces the activation energy barrier required for the cross-coupling reaction.