A new water-soluble metal-free phthalocyanine substituted with naphthoxy-4-sulfonic acid sodium salt. Synthesis, aggregation, electrochemistry and in situ spectroelectrochemistry

Arslan, Sonmez; Yılmaz, İsmail

doi:10.1016/j.poly.2006.11.047

Cited by 41 publications

(16 citation statements)

References 35 publications

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“…As can be seen, the spectra of the reduced species shows well-defined isosbestic points observed at λ = 323 and 383 nm, confirming that the electrode reaction proceeds in a quantitative fashion and therefore the absence of any coupled chemistry. [43][44][45][46] The complex showed distinctive spectral changes that the intensity of the band (λ = at 364 nm, assigned to n → π* transitions) decreased and a new broad band in low intensity about 460 nm appeared as a result of the reduction of the nickel centered in the oxime core.…”

Section: Electrochemistrymentioning

confidence: 99%

Synthesis, spectroscopic and redox properties of the mononuclear NiII, NiII(BPh2)2 containing (B-C) bond and trinuclear CuII-NiII-CuII type-metal complexes of N,N′-(4-amino-1-benzyl piperidine)-glyoxime

2009

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The novel vic-dioxime ligand containing the 4-amino-1-benzyl piperidine group, N,N′-(4amino-1-benzyl piperidine)-glyoxime, (LH 2 ) has been prepared from 4-amino-1-benzyl piperidine with anti-dichloroglyoxime at -15°C in absolute THF. Mononuclear Ni II metal complex has been obtained with 1 : 2 metal/ligand ratio. The Ni II complex of this ligand is proposed to be square planar geometry. IR spectra show that the ligand acts in a tetradentate manner and coordinates N 4 donor groups of LH 2 to Ni II ion. The detection of H-bonding (O-H⋅⋅⋅O) in the [Ni(LH) 2 ] (1) metal complex by IR spectra supported the square-planar MN 4 coordination of mononuclear complex. The disappereance of H-bonding (O-H⋅⋅⋅O) in the [Ni(L) 2 (BPh 2 ) 2 ] (2) complex shows that the BPh + 2 -capped groups (BPh + 2 cation formed BPh 4 anion) attaches to the main oxime core. MN 4 coordination of the [Ni(LH) 2 ] (1) and [Ni(L) 2 (BPh 2 ) 2 ] (2) metal complexes were also determined by 1 H-NMR spectroscopy. In the trinuclear Cu II -Ni II -Cu II metal complexes, the Ni II ion centered into the main oxime core by the coordination of the imino groups while the two Cu II ions coordinate dianionic oxygen donors of the oxime groups and linked to the ligands of 1,10-phenanthroline, 2,2′-bipyridine, and 4,4′-bipyridine. The ligand and their mono and trinuclear metal complexes were characterized by elemental analyses, FT-IR, UV-Vis, 1 H and 13 C-NMR spectra, magnetic susceptibility measurements, molar conductivity, cyclic voltammetry, mass spectra and X-ray powder techniques. The cyclic voltammetric results show that the cathodic peak potential of [Ni(L) 2 (BPh 2 ) 2 ] shifted toward more negative value compared to that of [Ni(LH) 2 ], probably due to a decreasing effect of back donation of metal-oxime moieties as a result of the BPh + 2 -bridged complex formation. Also, the formation of the trinuclear Cu II -Ni II -Cu II metal complexes caused considerable changes on the CV behaviour of mononuclear [Ni(LH) 2 ] (1) complex. The spectroelectrochemical study of [Ni(L) 2 (BPh 2 ) 2 ] (2) showed distinctive spectral changes that the intensity of the band (λ = at 364 nm, assigned to n → π* transitions) decreased and a new broad band in low intensity about 460 nm appeared as a result of the reduction of the nickel centered in the oxime core.

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Section: Electrochemistrymentioning

confidence: 99%

Synthesis, spectroscopic and redox properties of the mononuclear NiII, NiII(BPh2)2 containing (B-C) bond and trinuclear CuII-NiII-CuII type-metal complexes of N,N′-(4-amino-1-benzyl piperidine)-glyoxime

2009

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“…9 Uptake and distribution are also a function of specific targeting motifs appended to the dye, and degree of aggregation. 6, 9 Appending ionic groups on the Pc macrocycle such as sulfonic groups, 10 quaternary amino or pyridinium groups 11, 12 makes them water soluble but the purification of these compounds can be a problem. Neutral, polar Pcs can be prepared by attaching hydroxyl groups.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photophysics of an octathioglycosylated zinc(II) phthalocyanine

Aggarwal

Singh

Ya-zhou

et al. 2011

Tetrahedron Letters

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A water soluble zinc(II) phthalocyanine symmetrically appended with eight thioglucose units was synthesized from commercially available hexadecafluorophthalocyaninatozinc(II) by controlled nucleophilic substitution of the peripheral fluoro groups. The photophysical properties and cancer cell uptake studies of this nonhydrolyzable thioglycosylated phthalocyanine are reported. The new compound has amphiphilic character, is chemically stable, and can potentially be used as a photosensitizer in photodynamic therapy.

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“…NhtCuPc, 2, 9, 16, 23-tetrakis(4-(1-naphthoxy-4-sulfonic acid sodium salt)) phthalocyaninato copper(II), was prepared by the complexation reaction of 2,9,16,23-tetrakis(4-(1-naphthoxy-4-sulfonic acid sodium salt)) phthalocyanine (NhtH 2 Pc) [16] and anhydrous copper acetate with moderate yield in methanol solution [17] (Fig. 1a).…”

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confidence: 99%

Preparation, electrochemical, and spectroelectrochemical characterization of a new water-soluble copper phthalocyanine

Arslan

Yılmaz

2007

Inorganic Chemistry Communications

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A new water-soluble metal-free phthalocyanine substituted with naphthoxy-4-sulfonic acid sodium salt. Synthesis, aggregation, electrochemistry and in situ spectroelectrochemistry

Cited by 41 publications

References 35 publications

Synthesis, spectroscopic and redox properties of the mononuclear NiII, NiII(BPh2)2 containing (B-C) bond and trinuclear CuII-NiII-CuII type-metal complexes of N,N′-(4-amino-1-benzyl piperidine)-glyoxime

Synthesis, spectroscopic and redox properties of the mononuclear NiII, NiII(BPh2)2 containing (B-C) bond and trinuclear CuII-NiII-CuII type-metal complexes of N,N′-(4-amino-1-benzyl piperidine)-glyoxime

Synthesis and photophysics of an octathioglycosylated zinc(II) phthalocyanine

Preparation, electrochemical, and spectroelectrochemical characterization of a new water-soluble copper phthalocyanine

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