1661-03-6Relevant articles and documents
Synthesis and structural characterization of a magnesium phthalocyanine(3) anion
Wong, Edwin W.Y.,Leznoff, Daniel B.
, p. 154 - 162 (2012)
The reduction of magnesium phthalocyanine (MgPc) with 2.2 equivalents of potassium graphite in 1,2-dimethoxyethane (DME) gives [K2(DME) 4]PcMg(OH)(1) in 67% yield. Compound 1 was structurally characterized using single crystal X-ray crystallography and was found to be a monomeric, heterometallic complex consisting of a μ3-OH ligand that bridges a [MgIIPc3-]- anion to two potassium cations solvated by four DME molecules. An absorption spectrum of 1 confirms the Pc ligand is singly reduced and has a 3charge. The solid-state structure of 1 does not indicate breaking of the aromaticity of the Pc ligand. Compound 1 is only the second Pc3- complex and the first reduced MgPc to be isolated and structurally characterized.
Magnesium(ii) 1-(1-adamantylsulfanyl)phthalocyanine-synthesis, photochemical and electrochemical properties
Kryjewski, Michal,Rebis, Tomasz,Milczarek, Grzegorz,Gdaniec, Zofia,Goslinski, Tomasz,Mielcarek, Jadwiga
, p. 9774 - 9780 (2016)
A mixed macrocyclization reaction of 3-(1-adamantylsulfanyl)-1,2-dicyanobenzene and 1,2-dicyanobenzene led to unsymmetrical magnesium(ii) 1-(1-adamantylsulfanyl)phthalocyanine. The novel macrocycle was characterized using UV-Vis, MS MALDI and NMR spectroscopy. The spectroscopic study of solvatochromic effects indicated that the changes observed in the electronic absorption spectra are mainly a result of solvation, and that the coordinating strength of the solvent had little influence on the red shift. The novel magnesium(ii) phthalocyanine derivative revealed in DMF and DMSO the fluorescence quantum yield (Φf) values of 0.30 and 0.35, and singlet oxygen quantum yield (ΦΔ) values of 0.32 and 0.25, respectively. The magnesium(ii) phthalocyanine derivative displayed in the voltammetric study four sets of redox peaks, two one-electron oxidations, and two one-electron reductions, which were assigned to ring based one electron processes.
Synthesis and coordination chemistry of unsymmetrical tetraazaporphyrins containing single oxathia- and thiacrown substituents
Lange, Steven J.,Sibert, John W.,Barrett, Anthony G.M.,Hoffman, Brian M.
, p. 7371 - 7377 (2000)
Singly crowned porphyrazines containing oxathia- and thiacrown ethers were prepared from a mixed condensation of 1,2-dicyanobenzene or its 3,4-dibutyl analog and the appropriate crowned maleonitrile precursor. Peripheral metal-binding to each porphyrazine was examined spectrophotometrically. The oxathiaether-crowned porphyrazines were found to coordinate Ag(I) and HgCl2, though all complexes suffered from poor solubility and complexes with the latter were unstable in polar media. With an interest in the formation of comparatively more stable and soluble heavy and transition metal complexes, two new sets of thiaether-crowned porphyrazines were examined. In these cases, coordination of Hg(II), Ag(I), Cu(I) and Cu(II) was observed with no evidence for complexation of Tl(I), Pb(II) or CdCl2. (C) 2000 Elsevier Science Ltd.
Improved syntheses of meso-aryl tetrabenzotriazaporphyrins (TBTAPs)
Alharbi, Nuha,Díaz-Moscoso, Alejandro,Tizzard, Graham J.,Coles, Simon J.,Cook, Michael J.,Cammidge, Andrew N.
, p. 7370 - 7379 (2016/02/03)
New tetrabenzotriazaporphyrins are reported that are functionalised at the meso-position. The derivatives functionalised with meso-bromophenyl substituents are synthesised using an improved variation on the traditional reaction between phthalonitriles and Grignard reagents. For all other new derivatives, a modern protocol is employed that gives convenient access to these challenging materials by template co-macrocyclisation between phthalonitriles and aryl-aminoisoindoline derivatives like 15. The newly developed procedure allows design and synthesis of elaborate, functional composites and this is demonstrated by synthesis of meso-pyrenylTBTAP 24, a linked double chromophore in which the two complementary units lie perpendicular to each other and therefore have minimal ground state interaction.
