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.
Photophysical properties and photocytotoxicity of free and liposome-entrapped diazepinoporphyrazines on LNCaP cells under normoxic and hypoxic conditions
Wieczorek, Ewelina,Mlynarczyk, Dariusz T.,Kucinska, Malgorzata,Dlugaszewska, Jolanta,Piskorz, Jaroslaw,Popenda, Lukasz,Szczolko, Wojciech,Jurga, Stefan,Murias, Marek,Mielcarek, Jadwiga,Goslinski, Tomasz
, p. 64 - 73 (2018)
5,7-Diaryl-substituted symmetrical diazepinoporphyrazine and tribenzodiazepinoporphyrazine were synthesized and characterized using UV–Vis, MS MALDI, and various NMR techniques. The expected photosensitizing potentials of these porphyrazines were evaluate
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.
RAPID PHOTOREDUCTION OF METHYL VIOLOGEN WITH VISIBLE LIGHT USING METAL-PHTHALOCYANINES AS SENSITIZERS.
Tanno,Woehrle,Kaneko,Yamada
, p. 1032 - 1034 (1980)
Metal phthalocyanines (MtPc), which are corresponding in their structure to the natural porphines, are interesting in solar energy conversion. The MtPc show activity as sensitizers in photoredox reactions with the aim of H//2-evolution from water. Methyl viologen is reduced through the MtPc effectively in quantum yields till 47% in an organic solvent/water mixture.
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.
Group IIA alkaline-earth metal phthalocyanines: Synthesis, photoluminescence and singlet oxygen formation
Liu, Limin,Zhang, Xian-Fu
, (2021/09/14)
We have synthesized Group IIA alkaline-earth metal phthalocyanine (PC) complexes (BePC, MgPC, CaPC, SrPC, BaPC) using four different methods to study their photoluminescence and singlet oxygen photosensitizing properties. Their UV–Vis electronic absorptio
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.
Synthesis of (2,3-diphenyl)pyrazinotribenzoporphyrazine
Kokareva,Khelevina
, p. 1484 - 1489 (2013/06/26)
By the method of template cyclotetramerization magnesium(II) (2,3-diphenyl)pyrazinotribenzoporphyrazinate was synthesized, and it was converted into (2,3-diphenyl)pyrazinotribenzoporphyrazine. (2,3-Diphenyl)- pyrazinotribenzoporphyrazine and (2-phenyl)imi
Synthesis and spectroscopic properties of low-symmetry tribenzoporphyrazines with annulated 6H-1,4-diazepine ring
Donzello, Maria Pia,Ercolani, Claudio,Mannina, Luisa,Viola, Elisa,Bubnova, Alena,Khelevina, Ol'ga G.,Stuzhin, Pavel A.
, p. 262 - 272 (2008/09/20)
Template co-condensation of 2,3-dicyano-5,7-diphenyl-6H-1,4-diazepine 1 with 10-fold molar excess of phthalodinitrile 2 in the presence of Mg II propoxide or butoxide in the corresponding alcohol leads to a mixture of MgII-diazepinoporphyrazines 3?6 from which the low symmetry 3:1 species 3, which contains three annulated benzene and one 1,4-diazepine rings, is separated by column chromatography as the aquo complex, [2,4-diphenyltribenzo[b,g,l][1,4]diazepino[2,3-q]porphyrazinato(aquo) magnesium(ii)], [Bz3DzPzMg(H2O)]. The complex 3 can be demetalated in acetic or trifluoroacetic acids under mild conditions with formation of the corresponding free-base [Bz3DzPzH2] 3a. This latter is also formed by co-cyclotetramerization of the same precursors 1 and 2 in the presence of sodium ethoxide in ethanol or lithium butoxide in butanol followed by demetalation of the intermediate disodium or dilithium salts in acid medium. The constitution and structure of the obtained compounds were established on the basis of elemental analysis, mass spectrometry, and 1H NMR spectra. The variable temperature 1H NMR measurements provide evidence that in porphyrazines 3 and 3a the 1,4-diazepine ring exists predominantly in the 6H-form over a wide temperature range. The free energy of activation for the inversion of the 1,4-diazepine ring determined for 3 is 45.6 ± 1.7 kJ mol?1. Solution UV-visible spectra measurements in acidic media (CH2Cl2/CF3COOH) provide evidence that the MgII complex 3 is easily protonated on the meso-N atom of the porphyrazine macrocycle followed by slow demetallation with formation of the free base 3a in its neutral form or as a species protonated on the diazepine ring. CSIRO 2008.
Novel synthesis of phthalocyanines from phthalonitriles under mild conditions
Uchida, Hitoshi,Tanaka, Hirokazu,Yoshiyama, Hideyuki,Reddy, Paidi Yella,Nakamura, Shuichi,Toru, Takeshi
, p. 1649 - 1652 (2007/10/03)
A convenient preparation of phthalocyanines from phthalonitriles was accomplished by treatment with metal salts and hexamethyldisilazane (HMDS) in DMF at 100 °C. This reaction provides a new preparative method under mild conditions for phthalocyanines having a variety of metals and substituted phthalocyanines as well as Zn-naphthalocyanine.
