Synthesis, spectroscopic characterization and thermogravimetric analysis of two series of substituted (metallo)tetraphenylporphyrins.

Subsequent treatment of HTPP(COH) (tetra(-carboxylic acid phenyl)porphyrin, ) with an excess of oxalyl chloride and HNR afforded HTPP(C(O)NR) (R = Me, ; iPr, ) with yields exceeding 80%. The porphyrins and could be converted to the corresponding metalloporphyrins MTPP(C(O)NR) (R = Me/iPr for M = Zn (, ); Cu (, ); Ni (, ); Co (, )) by the addition of 3 equiv of anhydrous MCl (M = Zn, Cu, Ni, Co) to dimethylformamide solutions of and at elevated temperatures. Metalloporphyrins - and - were obtained in yields exceeding 60% and have been, as well as and , characterized by elemental analysis, electrospray ionization mass spectrometry (ESIMS) and IR and UV-vis spectroscopy. Porphyrins , - and , - are not suitable for organic molecular beam deposition (OMBD), which is attributed to their comparatively low thermal stability as determined by thermogravimetric analysis (TG) of selected representatives.