Synthesis and purification of metallooctachlorophthalocyanines

Abstract

A detailed synthetic procedure based on the use of urea, dichlorophthalic acid, respective transition metal halides and [NH4]2[MoO4] as a catalyst in the melt or by using 1,2,4-trichlorobenzene as a high-boiling inert solvent is described to gain 2,3,9,10,16,17,23,24-metallooctachlorophthalocyanines (MPcCl8 compounds with M=Mn, Fe, Co, Ni, Cu). In cases that a first purification by subsequent treatment of the crude materials with HCl, NaOH and HCl would not give rise to analytically pure compounds, a second novel purification by using pyridine is described. The degree of purity, exceeding always 98%, is determined by thermogravimetric analysis. Comparative IR, UV/Vis and PXRD studies of the MPcCl8 compounds are reported.

Chlorosubstituted Copper Phthalocyanines: Spectral Study and Structure of Thin Films

“…Based on these data, the CuPcCl 16 diffraction pattern was indexed, and the unit cell parameters were refined using the 2θ positions of the diffraction peaks measured from the powder diffraction pattern (see Table S6). [36], which match well with the strongest peaks observed in our XRD data. Therefore, the appropriate unit cell parameters for CuPcCl 8 were found using the DICVOL14 indexing program [37].…”

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

“…0.5%. Furthermore, the measurement conditions of an EA may influence results as recently demonstrated for a series of octachlorometallophthalocyanines of the type MPcCl 8 (M II = Cu, Ni, Co, Fe, Mn) [ 20 ]. However, for the herein reported porphyrins 2 and 3 and their corresponding metalloporphyrins 2a – d and 3a – d the CHN contents deviate by at most ±0.5%.…”

Cobalt(iii)-containing penta-dentate “helmet”-type phthalogens: synthesis, solid-state structures and their thermal and electrochemical characterization

“…13–38 However, another simpler synthetic route involve the direct use of 1,3-diiminoisoindoline have been reported. 10,39 Additionally, 1,3-diiminoisoindoline is also useful for the synthesis of various phthalocyanine analogues, such as subphthalocyanine, 40 hemiporphyrazines, 41 metal chelates such as the bis(iminopyridyl)isoindoline 42 and phthalazine ligands. 43 In early 1950s, Linstead synthesized 1,3-diiminoisoindoline from the addition of liquid ammonia in a methanolic solution of phthalonitrile; the reaction mixture was heated in an autoclave for four hours to yield a beige/light green product.…”