Synthesis of 21,23-Selenium- and Tellurium-Substituted 5‑Porphomethenes, 5,10-Porphodimethenes, 5,15-Porphodimethenes, and Porphotrimethenes and Their Interactions with Mercury

The 3+1 condensation of symmetrical 16-Selena/telluratripyrranes with symmetrical selenophene-2,5-diols/tellurophene-2,5-diols in the presence of BF₃-etheratre or BF₃-methanol followed by oxidation with DDQ gave 5,10-porphodimethenes, whereas the process with unsymmetrical selenophene-2,5-diols/tellurophene-2,5-diols gave 5-porphomethenes. In addition, the reaction of unsymmetrical 16-Selena/telluratripyrranes with symmetrical selenophene-2,5-diols/tellurophene-2,5-diols gave the corresponding porphotrimethenes, whereas the process with unsymmetrical selenophene-2,5-diols/tellurophene-2,5-diols gave the 5,15-porphodimethenes. The structures of different products were characterized by IR, ¹H and ¹³C NMR, ¹H–¹H COSY, CHN analysis, and mass spectrometry. The binding of mercury with the calix[4]­phyrins mentioned above had been observed in the decreasing order of porphodimethenes > porphomethenes > porphotrimethenes by UV–vis and ¹H NMR spectroscopy.