Alternative donor-acceptor stacks from crown ethers and naphthalene diimide derivatives: rapid, selective formation from solution and solid state grinding.

The atypical 1:2 complexation between an electron-rich crown ether host and electron-deficient naphthalene diimide-based guests led to the formation of alternative donor-acceptor (ADA) stacks. The ADA stacks can be expediently obtained in high yield as polycrystalline aggregates from solution. More remarkably, the high degree of organization has also been realized in a simple solid-to-solid mechanical grinding process. The solid-state structures have been verified by solid-state NMR spectroscopy, single crystal, and powder X-ray diffraction analysis. The current findings not only provide convenient ways of obtaining novel donor-acceptor stacks involving a macrocyclic host but also represent an important step in transferring electroactive host-guest systems from solution to the solid state.