Self-Sorted Assembly in a Mixture of Donor and Acceptor Chromophores

A simple and novel supramolecular approach for orthogonal self-assembly of donor and acceptor chromophores has been demonstrated. Suitably designed 1,5-dialkoxynaphthalene (DAN) and naphthalene tetracarboxylic acid diimide (NDI) derivatives were used as the donor and acceptor systems, respectively. The molecular design for self-sorting relies upon the precise control over the placement of the self-complementary hydrogen-bonding units (amide functionality) with respect to the individual chromophore. By design, the distances between the two amide groups in the donor and acceptor chromophores are not identical, and consequently the effect of the hydrogen-bonding interaction cannot be maximised in the case of alternate donor-acceptor-type pi-stacking. Thus a relatively weak charge-transfer interaction is expected to be sacrificed, and segregated assembly among the individual chromophores should be enforced by virtue of the much stronger effects of hydrogen bonding and pi-pi stacking. Detailed spectroscopic studies were carried out to probe the mode of self-assembly in various derivatives of the DAN-NDI donor-acceptor pairs to establish the utility of the molecular design as a generalised one for orthogonal self-assembly.