Synthesis, structural characterization, and anion binding ability of sterically congested adamantane-calix[4]pyrroles and adamantane-calixphyrins

Novel adamantane derivatives of calix[4]pyrroles 4–8 and calixphyrin 9 have been synthesized. The structure of 8 has been characterized by X-ray powder diffraction and the structure of 9 by single crystal X-ray analysis. Whereas calixphyrin 9 does not bind anions, analogous calyx[4]pyrrole 8 forms a complex with Cl− in the DMSO solution and in the solid state. The solid state complexation has been accomplished on grinding in a mill, which is the first example of complex formation with an anion in the solid state.