Synthesis, structure and properties of coordination compounds of iron phthalocyanines and their analogues

Nemykin, V. N.; Tretyakova, Iryna; Волков, С. В.; Li, V D; Mekhryakova, N G; Kaliya, O. L.; Luk’yanets, E. A.

doi:10.1070/rc2000v069n04abeh000545

Cited by 25 publications

(28 citation statements)

References 165 publications

(232 reference statements)

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“…In light of Lever’s work and the considerable academic and industrial interest surrounding iron phthalocyanine (PcFe II ) derivatives, − this work focuses on expanding the already rich chemistry of these complexes. Indeed, iron phthalocyanine complexes have been studied as catalysts for C–H bond activation, − electrocatalysts for the oxygen reduction reaction, − active components for catalytic cancer therapy, , platforms for optical detection of small molecules, − and composite materials for electrochemical detection of biologically relevant species. − The axial coordination of nitrogen bases, − phosphines and phosphites, − nitroso compounds, sulfoxides and sulfides, − carbon monoxide, − and isonitriles − to iron(II) phthalocyanine was studied by UV–visible, NMR, and Mössbauer spectroscopies as well as by crystallography.…”

Section: Introductionmentioning

confidence: 99%

Application of Lever’s E_L Parameter Scale toward Fe(II)/Fe(III) versus Pc(2-)/Pc(1-) Oxidation Process Crossover Point in Axially Coordinated Iron(II) Phthalocyanine Complexes

et al. 2021

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The electronic structures and, particularly, the nature of the HOMO in a series of PcFeL 2 , PcFeL′L″, and [PcFeX 2 ] 2− complexes (Pc = phthalocyaninato(2-) ligand; L = NH 3 , n-BuNH 2 , imidazole (Im), pyridine (Py), PMe 3 , PBu 3 , t-BuNC, P(OBu) 3 , and DMSO; L′ = CO; L″ = NH 3 or n-BuNH 2 ; X = NCO − , NCS − , CN − , imidazolate (Im − ), or 1,2,4triazolate(Tz − )) were probed by electrochemical, spectroelectrochemical, and chemical oxidation as well as theoretical (density functional theory, DFT) studies. In general, energies of the metal-centered occupied orbitals in various six-coordinate iron phthalocyanine complexes correlate well with Lever Electrochemical Parameter E L and intercross the phthalocyaninecentered a 1u orbital in several compounds with moderate-to-strong π-accepting axial ligands. In these cases, an oxidation of the phthalocyanine macrocycle (Pc(2-)/Pc(1-)) rather than the central metal ion (Fe(II)/Fe(III)) was theoretically predicted and experimentally confirmed.

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Section: Introductionmentioning

confidence: 99%

Application of Lever’s E_L Parameter Scale toward Fe(II)/Fe(III) versus Pc(2-)/Pc(1-) Oxidation Process Crossover Point in Axially Coordinated Iron(II) Phthalocyanine Complexes

et al. 2021

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“…The instability of unligated iron naphthalocyanines have been reported previously [10], whereas bis-ligated iron naphthalocyanines are stable and could be studied for their properties in solution [11,12]. The fact that bis-ligated iron octabutoxynaphthalocyanine is unstable even in solid state suggests that the electron-donating butoxy groups destabilize the iron complex.…”

Section: Resultsmentioning

confidence: 91%

The synthesis and properties of iron, ruthenium, and osmium octabutoxynaphthalocyanine

Kim

Kenney

2012

J. Porphyrins Phthalocyanines

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New series of iron, ruthenium, and osmium octabutoxynaphthalocyanines were synthesized by inserting corresponding metals into the metal-free octabutoxynaphthalocyanine. Although preparation of axial ligand-free iron octabutoxynaphthalocyanines was reported before, we could not reproduce the synthesis by following the reported method. We attributed the failure to the instability of the iron octabutoxynaphthalocyanines. Bis-ligation increased the stability of the iron complex but only sufficiently for characterization. The application of iron complexes will be limited by their instability. However, ruthenium and osmium formed stable complexes with this macrocycle ring but with significantly lower reaction yields. These new complexes were characterized by NMR, UV-vis, and mass spectrometry.

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“…Iron phthalocyanine has very low solubility in most organic solvents and high tendency to aggregation that arises from stronginteractions between aromatic Pc-macrorings [4,5]. FePc also exhibits a pronounced tendency to axial ligation with many additive FePc-complexes obtained by recrystallization of FePc from solvents with donors [6].…”

Section: Introductionmentioning

confidence: 98%

Structural characterization of two modifications of bis(4-methylpyridine)phthalocyaninato(2-)iron(II) complex

Janczak

Kubiak

2012

Journal of Coordination Chemistry

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Two crystalline modifications, orthorhombic (II) and triclinic (III), of bis(4-methylpyridine) iron(II) phthalocyanine are obtained. The orthorhombic (II) crystals are formed from solvated crystals of FePc(4-Mepy) 2 Á 2(4-Mepy) (I) after storing at room temperature in ambient air. The crystals I releasing the solvated 4-Mepy molecules transform into crystals II without destruction of the crystalline network. Releasing solvated 4-Mepy molecules from I and formation of II lead to co-operative translation of the neighboring zig-zag ribbons of FePc(4-Mepy) 2 and contraction of the lattice parameters. Triclinic crystals of FePc(4-Mepy) 2 (III) are formed at higher temperature than the orthorhombic, but solvated crystals of FePc(4-Mepy) 2 Á 2(4-Mepy) (I). Electron paramagnetic resonance and magnetic susceptibility measurements clearly show ligation of the iron(II) phthalocyanine by 4-Mepy molecules leads to the change of the ground state from S ¼ 1 (for FePc, e 3 g b 2 2g a 1 1g ) to S ¼ 0 (FePc(4-Mepy) 2 , e 4 g b 2 2g ). Thus FePc(4-Mepy) 2 is a low-spin complex. The FePc(4-Mepy) 2 complex was also characterized by thermogravimetric analysis and UV-Vis spectroscopy.

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Synthesis, structure and properties of coordination compounds of iron phthalocyanines and their analogues

Cited by 25 publications

References 165 publications

Application of Lever’s E_L Parameter Scale toward Fe(II)/Fe(III) versus Pc(2-)/Pc(1-) Oxidation Process Crossover Point in Axially Coordinated Iron(II) Phthalocyanine Complexes

Application of Lever’s E_L Parameter Scale toward Fe(II)/Fe(III) versus Pc(2-)/Pc(1-) Oxidation Process Crossover Point in Axially Coordinated Iron(II) Phthalocyanine Complexes

The synthesis and properties of iron, ruthenium, and osmium octabutoxynaphthalocyanine

Structural characterization of two modifications of bis(4-methylpyridine)phthalocyaninato(2-)iron(II) complex

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Synthesis, structure and properties of coordination compounds of iron phthalocyanines and their analogues

Cited by 25 publications

References 165 publications

Application of Lever’s EL Parameter Scale toward Fe(II)/Fe(III) versus Pc(2-)/Pc(1-) Oxidation Process Crossover Point in Axially Coordinated Iron(II) Phthalocyanine Complexes

Application of Lever’s EL Parameter Scale toward Fe(II)/Fe(III) versus Pc(2-)/Pc(1-) Oxidation Process Crossover Point in Axially Coordinated Iron(II) Phthalocyanine Complexes

The synthesis and properties of iron, ruthenium, and osmium octabutoxynaphthalocyanine

Structural characterization of two modifications of bis(4-methylpyridine)phthalocyaninato(2-)iron(II) complex

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Application of Lever’s E_L Parameter Scale toward Fe(II)/Fe(III) versus Pc(2-)/Pc(1-) Oxidation Process Crossover Point in Axially Coordinated Iron(II) Phthalocyanine Complexes

Application of Lever’s E_L Parameter Scale toward Fe(II)/Fe(III) versus Pc(2-)/Pc(1-) Oxidation Process Crossover Point in Axially Coordinated Iron(II) Phthalocyanine Complexes