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Synthesis, Structure, and Complexation Properties of Partially and Completely Reduced meso-Octamethylporphyrinogens (Calix[4]pyrroles)


  • This work was supported by the Swiss National Science Foundation (Grant No. 2000-067057.01) and the University of Neuchâtel. This work is part of the thesis of V.B. We thank Dipl.-Chem. Michael Schmid (Neuchâtel), Dr. Lydia Brelot (Neuchâtel), and Christopher Jones (Cambridge) for preliminary experiments.


New tricks for an old dog: Calixpyrroles bind anions efficiently and can be transformed into transition-metal complexes only under forcing conditions. Reducing the macrocycle creates a ligand that easily forms classical Werner complexes with copper, nickel, and palladium ions. The metal complexes present an array of four directed hydrogen bonds, which specifically bind the counterions (see picture; blue N, white H, green Cl, red Cu, Ni, or Pd).

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