Pentalysine β‐Carbonylphthalocyanine Zinc: An Effective Tumor‐Targeting Photosensitizer for Photodynamic Therapy

Unsymmetrical phthalocyanine derivatives have been widely studied as photosensitizers for photodynamic therapy (PDT), targeting various tumor types. However, the preparation of unsymmetrical phthalocyanines is always a challenge due to the presence of many possible structural isomers. Herein we report a new unsymmetrical zinc phthalocyanine, pentalysine β‐carbonylphthalocyanine zinc (ZnPc‐(Lys)₅), that was prepared in large quantity and high purity. This is a water‐soluble cationic photosensitizer and maintains a high quantum yield of singlet oxygen generation similar to that of unsubstituted zinc phthalocyanine (ZnPc). Compared with anionic ZnPc counterparts, ZnPc‐(Lys)₅ shows a higher level cellular uptake and 20‐fold higher phototoxicity toward tumor cells. Pharmacokinetics and PDT studies of ZnPc‐(Lys)₅ in S180 tumor‐bearing mice showed a high ratio of tumor versus skin retention and significant tumor inhibition. This new molecular framework will allow synthetic diversity in the number of lysine residues incorporated and will facilitate future QSAR studies.     

Solubilization of phthalocyanines into methanol with fluoroalkyl end‐capped N‐(1,1‐dimethyl‐3‐oxobutyl)‐ and N,N‐dimethyl‐acrylamide oligomers

Self‐assembled molecular aggregates of fluoroalkyl end‐capped N‐(1,1‐dimethyl‐3‐oxobutyl)‐ and N,N‐dimethyl‐acrylamide oligomers in methanol were found to interact with phthalocyanines as guest molecules to exhibit good solubility. On the other hand, the corresponding nonfluorinated oligomers were not effective in solubilizing phthalocyanines under similar conditions. In these oligomers, fluorinated N‐(1,1‐dimethyl‐3‐oxobutyl)acrylamide oligomers were more effective in solubilizing phthalocyanines in methanol. Self‐assemblies formed by fluorinated oligomer‐phthalocyanine complexes are applied to the surface modifications of polystyrene (PS), and the modified PS surface exhibited not only a strong oleophobicity imparted by fluorine but also good hydrophilicity. Thus, these fluorinated molecular aggregate‐phthalocyanine systems are suggested to have high potential for new fluorinated functional materials through their excellent properties imparted by fluorine and phthalocyanines. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 93: 521–525, 2004     

Synthesis and spectroscopic characterisation of non‐aggregated novel axially 4‐{2‐[3‐(diethylamino)phenoxy]ethoxy} and crown ether substituted silicon phthalocyanines

This paper describes the synthesis and spectroscopic characterisation of a range of new axially disubstituted silicon phthalocyanines, with 4‐{2‐[3‐(diethylamino)phenoxy]ethoxy}, 4‐(1,4,7,10‐tetraoxacyclododecan‐2‐ylmethoxy) and 4‐(1,4,7,10,13,16‐hexaoxacyclooctadecan‐2‐ylmethoxy) groups as axial ligands. These axially disubstituted silicon phthalocyanine complexes were synthesised for the first time here. The newly synthesised silicon phthalocyanines were characterised by ultraviolet–visible, infrared, proton and carbon nuclear magnetic resonance spectroscopy, electrospray ionisation mass spectrometry and elemental analysis. The aggregation behaviour of these compounds was investigated in different concentrations of chloroform and the effects of various organic solvents on the absorption spectra were studied.     

Magnetic properties of polystyrene‐b‐poly(2‐hydroxylethyl methacrylate)/metal hybrids

Hybrids, which were composed of the amphiphilic diblock copolymer polystyrene‐b‐poly(2‐hydroxylethyl methacrylate) (PSt‐b‐PHEMA) and nickel, cobalt, or a nickel–cobalt alloy, were characterized with infrared absorption spectroscopy and ultraviolet–visible (UV–vis) absorption spectroscopy. UV–vis spectroscopy analysis showed that a redshift happened after the PSt‐b‐PHEMA/metal‐ion complexes were reduced by KBH₄. The PSt‐b‐PHEMA/nickel–cobalt alloy hybrids had the biggest redshift [difference of the UV‐vis absorption wavelength between (PSt‐b‐PHEMA)/metal ion complex and (PSt‐b‐PHEMA)/metal hybrids (Δλ_m = 19.9 nm)]. In comparison with the PSt‐b‐PHEMA/nickel hybrids (Δλ_m = 3.5 nm) and PSt‐b‐PHEMA/cobalt hybrids (Δλ_m = 9.0 nm). The magnetic properties of PSt‐b‐PHEMA/metal were studied with vibrating sample magnetometry. The results of magnetic hysteresis loop studies showed that the obtained PSt‐b‐PHEMA/metal hybrids could be categorized as ferromagnetic materials. The results showed that the magnetic susceptibility decreased with increasing temperature in the range of 150–400 K and increased with increasing temperature above 400 K. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci, 2006     

Poly(2‐acrylamido glycolic acid‐co‐2‐acrylamido‐2‐methyl‐1‐propane sulfonic acid): Synthesis,characterization, and retention properties for environmentally impacting metal ions

Poly(2‐acrylamido glycolic acid‐co‐2‐acrylamido‐2‐methyl‐1‐propane sulfonic acid) [P(AGA‐co‐APSA)] was synthesized by radical polymerization in an aqueous solution. The water‐soluble polymer, containing secondary amide, hydroxyl, carboxylic, and sulfonic acid groups, was investigated, in view of their metal‐ion‐binding properties, as a polychelatogen with the liquid‐phase polymer‐based retention technique under different experimental conditions. The investigated metal ions were Ag⁺, Co²⁺, Ni²⁺, Cu²⁺, Zn²⁺, Cd²⁺, Pb²⁺, and Cr³⁺, and these were studied at pHs 3, 5, and 7. P(AGA‐co‐APSA) showed efficient retention of all metal ions at the pHs studied, with a minimum of 60% for Co(II) at pH 3 and a maximum close to 100% at pH 7 for all metal ions. The maximum retention capacity (n metal ion/n polymer) ranged from 0.22 for Cd²⁺ to 0.34 for Ag⁺. The antibacterial activity of Ag⁺, Cu²⁺, Zn²⁺, and Cd²⁺ polymer–metal complexes was studied, and P(AGA‐co‐APSA)–Cd²⁺ presented selective antibacterial activity for Staphylococcus aureus with a minimum inhibitory concentration of 2 μg/mL. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

Electrochemical and spectroelectrochemical characterization of the phthalocyanines with pentafluorobenzyloxy substituents

The solution redox properties and spectroelectrochemical investigation of the novel metal-free, zinc, nickel and cobalt phthalocyanines with tetra-pentafluorobenzyloxy substituents at the periphery were studied using various electrochemical and spectroelectrochemical measurements. Cyclic voltammetry and differential pulse voltammetry studies show that while Ni(II), Zn(II) and free-phthalocyanines give up to two reduction and two oxidation processes having ligand-based diffusion controlled reversible one-electron electron transfer characters, Co(II) phthalocyanine represents one ligand-based oxidation, one metal-based reduction and one ligand-based reduction processes having diffusion controlled reversible one-electron transfer characters. Assignments of the redox couples are also confirmed by spectroelectrochemical measurements. Reduction potentials of all complexes shift to positive potentials due to the electron withdrawing tetra-pentafluorobenzyloxy substituents compared with those of the phthalocyanines bearing phenoxy derivatives. A linear variation of the first reduction and oxidation potentials versus ze/r has been obtained for zinc and nickel phthalocyanines.     

Synthesis,Structure Characterization and Biological Activity of Co (II), Cu (II), and Zn (II) Complexes with (Z)‐3‐((3‐hydroxybenzylidene)amino)pyridin‐1‐ium 4‐(dodecan‐4‐yl)benzenesulfonate Surfactant

(Z)‐3‐((3‐hydroxybenzylidene)amino)pyridin‐1‐ium4‐dodecylbenzenesulfonate anionic surfactant and its cobalt, copper and zinc complexes were synthesized (I, I‐Co, I‐Cu and I‐Zn). The chemical structures of it were characterized by elemental analysis, FTIR, ¹H‐NMR, UV–Vis spectroscopy and atomic adsorption. The effects of the chemical structures of the synthesized anionic surfactant and the type of transition metals on the surface activity are presented in this paper. The thermodynamic parameters show that adsorption and micellization processes are spontaneous. The results of biological activity measurements showed that the synthesized compounds have a great efficiency against gram positive (Bacillus subtilis and Staphylococcus aureus), gram‐ negative bacteria (Pseudomonas aeruginosa and Escherichia coli) and fungi (Candida albicans and Aspergillus niger) as well as the sulfate reducing bacteria (Desulfomonas pigra). The complexation of the anionic surfactant with Co²⁺, Cu²⁺ and Zn²⁺ increase the antimicrobial activity values.     

Synthesis and characterization of conducting copolymer of Trans‐1‐(4‐methyl‐3′‐thienyl)‐2‐(ferrocenyl)ethene with EDOT

Ferrocene‐substituted conducting polymer namely poly(trans‐1‐(4‐methyl‐3′‐thienyl)‐2‐(ferrocenyl)ethene‐co‐3,4‐ethylenedioxythiophene) [P(MTFE‐co‐EDOT)] was synthesized and its electrochromic properties were studied. Monomer, MTFE, was obtained using 2‐(ferrocenyl)ethene and 3‐methyl‐4‐bromothiophene. The structure of monomer was determined via Fourier transform infrared spectroscopy (FTIR), ¹H‐NMR, and ¹³C‐NMR techniques. The copolymer was synthesized using this monomer and EDOT. The resulting copolymer P(MTFE‐co‐EDOT) was characterized by cyclic voltammetry, FTIR, scanning electron microscopy, atomic force microscopy, and UV–vis spectroscopy. The conductivity measurements of copolymer and PEDOT were accomplished by the four‐probe technique. Although poly(trans‐1‐(4‐methyl‐3′‐thienyl)‐2‐(ferrocenyl)ethene) [P(MTFE)] reveals no electrochromic activity, its copolymer with EDOT has two different colors (violet and gray). Band gap (E_g) and λ_max of P(MTFE‐co‐EDOT) were determined. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012     

Synthesis,characterization and polychelatogenic properties of poly[(2‐acrylamido‐2‐methyl‐1‐propane sulfonic acid)‐co‐(methacrylic acid)]

Poly(2‐acrylamido‐2‐methyl‐1‐propanesulfonic acid), poly(methacrylic acid), and five copolymers of poly[(2‐acrylamido‐2‐methyl‐1‐propanesulfonic acid)‐co‐(methacrylic acid)] were synthesized by radical polymerization and obtained in yields >97%. The polymers were characterized by FT‐IR, [¹H]NMR, and [¹³C]NMR and studied by means of the Liquid‐phase Polymer‐based Retention (LPR) technique. The metal ion retention ability of the copolymers for Cu(II), Cd(II), Co(II), Hg(II), Ni(II), Zn(II), Cr(III) and Ag(I) was investigated at different pH values because of their environmental and analytical interest. The retention profiles of the copolymers were compared with those of the corresponding homopolymers and retention of metal ions was found to increase with increasing pH. © 2001 Society of Chemical Industry     

Polyamides obtained by direct polycondesation of 4‐[4‐[9‐[4‐(4‐aminophenoxy)‐3‐methyl‐phenyl] fluoren‐9‐YL]‐2‐methyl‐phenoxy]aniline with dicarboxylic acids based on a diphenyl‐silane moiety

Polyamides (PAs) containing fluorene, oxyether, and diphenyl‐silane moieties in the repeating unit were synthesized in > 85% yield by direct polycondesation between a diamine and four dicarboxylic acids. Alternatively, one PA was synthesized from an acid dichloride. The diamine 4‐[4‐[9‐[4‐(4‐aminophenoxy)‐3‐methyl‐phenyl]fluoren‐9‐yl]‐2‐methyl‐phenoxy]aniline ( 3 ) was obtained from the corresponding dinitro compound, which was synthesized by nucleophilic aromatic halogen displacement from p‐chloronitrobenzene and 9,9‐bis (4‐hydroxy‐3‐methyl‐phenyl)fluorene ( 1 ). Monomers and polymers were characterized by FTIR and ¹H, ¹³C, and ²⁹Si‐NMR spectroscopy and the results were in agreement with the proposed structures. PAs showed inherent viscosity values between 0.14 and 0.43 dL/g, indicative of low molecular weight species, probably of oligomeric nature. The glass transition temperature (T_g) values were observed in the 188–211°C range by DSC analysis. Thermal decomposition temperature (TDT_10%) values were above 400°C due to the presence of the aromatic rings in the diamine. All PAs showed good transparency in the visible region (>88% at 400 nm) due to the incorporation of the fluorene moiety. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

Electropolymerization of a new 4‐(2,5‐Di‐2‐thiophen‐2‐yl‐pyrrol‐1‐yl)‐tetra substituted nickel phthalocyanine derivative

A new tetrakis 4‐(2,5‐di‐2‐thiophen‐2‐yl‐pyrrol‐1‐yl) substituted nickel phthalocyanine (NiPc‐SNS) was synthesized and characterized by elemental analysis, Fourier Transform Infrared (FT‐IR), and UV–vis spectroscopies. The electrochemical polymerization of this newly synthesized NiPc‐SNS was performed in dichloromethane (DCM)/tetrabutylammonium perchlorate (TBAP) solvent/electrolyte couple. An insoluble film was deposited on the electrode surface, both during repetitive cycling and constant potential electrolysis at 0.85 V. Resulting polymer film, P(NiPc‐SNS), was characterized utilizing UV–vis and FT‐IR spectroscopic techniques and its electrochemical behavior was investigated via cyclic voltammetry (CV). Spectroelectrochemical behavior of the polymer film on indium tin oxide (ITO) working electrode was investigated by recording the electronic absorption spectra, in situ, in monomer‐free electrolytic solution at different potentials and it is found that the P(NiPc‐SNS) film can be reversibly cycled between 0.0 and 1.1 V and exhibits electrochromic behavior; dark olive green in the neutral and dark blue in the oxidized states with a switching time of 1.98 s. Furthermore, the band gap of P(NiPc‐SNS) was calculated as 2.27 eV from the onset of π–π* transition of the conjugated backbone. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

Synthesis and electrochemical and in situ spectroelectrochemical characterization of manganese, vanadyl, and cobalt phthalocyanines with 2-naphthoxy substituents

Metallo (Mn, Co, VO) phthalocyanines bearing peripheral 2-naphthoxy groups were synthesized by cyclotetramerisation of the corresponding phthalonitrile derivative. The phthalocyanine compounds were characterized by elemental analyses, mass, FT-IR and UV–vis spectral data. Three intense bands in the electronic spectra clearly indicate the absorptions resulting from naphthyl groups along with the Q and B bands of the phthalocyanines. Electrochemical and spectroelectrochemical measurements exhibit that incorporation of redox active metal ions, Co^II and Mn^III, into the phthalocyanine core extends the redox capabilities of the Pc ring including the metal-based reduction and oxidation couples of the metal. Presence of molecular oxygen in the electrolyte system affects the voltammetric and spectroelectrochemical responses of the cobalt and manganese phthalocyanines due to the interaction between the complexes and molecular oxygen. Interaction reaction of oxygen with CoPc occurs via an “inner sphere” chemical catalysis process. While CoPc gives the intermediates [O₂⁻–Co^IIPc⁻²]⁻ and [O₂²–Co^IIPc⁻²]²⁻, MnPc forms μ-oxo MnPc species. An in situ electrocolorimetric method has been applied to investigate the color of the electro-generated anionic and cationic forms of the complexes for possible electrochromatic applications.     

Grafting of N,N′‐methylenebisacrylamide onto cellulose using Co(III)‐acetylacetonate complex in aqueous medium

The grafting of N,N′‐methylenebisacrylamide (N,N′‐MBA) onto cellulose is carried out using the cobaltacetylacetonate complex (Co(acac)₃) under nitrogen atmosphere at 40°C. The rate of graft copolymerization has been studied as a function of [N,N′‐MBA], [Co(acac)₃], and temperature. The activation energy of grafting is found to be 156.0 k J mol⁻¹ within the temperature range of 30–60°C. The effect of perchloric acid, methanol, and surfactants on graft yield has also been studied and results are suitably explained. The higher efficiency of the metal chelate in initiation of graft copolymerization has been assumed due to the coordination of the π electrons of the N,N′‐MBA with the metal chelate, which facilitated the formation of the radicals through homolytic cleavage of metal–oxygen bond of the cobalt acetylacetonate complex. On the basis of the results, a suitable kinetic scheme for graft copolymerization is presented and rate expression is derived. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 76: 906–912, 2000     

Electrochemical Reduction of Oxygen at Pyrolyzed Iron and Cobalt N4‐Chelates on Carbon Black Supports

Besides platinum, various nonnoble metal compounds, when prepared appropriately, are suitable for the electrochemical reduction of oxygen in liquid electrolytes and PEM‐fuel cells. Pyrolyzed N4‐chelates, such as phthalocyanines, tetraazaannulenes and porphyrins with a central metal atom of iron or cobalt, are a very important group of compounds and have been investigated in the past. It was found that the catalytic activity, especially of phthalocyanines, was high when prepared on carbon black supports at high temperatures (400–900 °C). Investigations on tetraazaannulenes and porphyrins yielded similar results. Non‐noble metal compounds of cyclame (1,4,8,11‐tetraazacyclotetradecane), which are also N4‐chelates, were not investigated as thoroughly. However, the catalytic activities of iron and cobalt cyclames were low, compared to those of phthalocyanines. With the (GC‐MS) analysis of both decomposition products, it could be shown that the mechanism of the N4‐chelate decomposition is of decisive importance for the catalytic activity.     

Chelation properties of poly(2‐hydroxy‐4‐acryloyloxybenzophenone) resins toward some divalent metal ions

The chelation behavior of poly(2‐hydroxy‐4‐acryloyloxybenzophenone) [poly(2H4ABP) or polymer I ] obtained through the free‐radical polymerization of 2‐hydroxy‐4‐acryloyloxybenzophenone monomer and for crosslinked polymers prepared from the monomer and known amounts of the crosslinker divinylbenzene (DVB) [4 mol % of DVB for polymer II, 8 mol % of DVB for polymer III, and 16 mol 16% of DVB for polymer IV ] toward the divalent metal ions Cu²⁺, Ni²⁺, Zn²⁺, and Pb²⁺ in aqueous solution was studied by a batch equilibration technique as a function of contact time and pH. The effect of the crosslinker, DVB, was also studied. The metal‐ion uptake of the polymers was determined with atomic absorption spectroscopy, and the highest uptake was achieved at pH 7.0 for polymers I, II, III, and IV. The selectivity and binding capacity of the resins toward the investigated divalent metal ions are discussed. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci 2008     

Optically Active 4‐Substituted (S)‐2‐Phenyl‐2‐oxazolines

(R)‐4‐Hydroxymethyl‐2‐phenyl‐2‐oxazoline (R)‐ 1 ) was prepared from (L)‐serine. The respective tosylate ((S)‐ 2 ) was converted into sulfides (S)‐ 4 and (S)‐ 5 , and sulfone (S)‐ 6 , useful starting materials for the elaboration of additional chiral centers. A previously reported [ α]_D ²⁵ value for (R)‐ 4 is corrected.     

Oxidation of aqueous sulfide solutions by dioxygen Part II: Catalysis by soluble and immobilized cobalt(II) phthalocyanines

The oxidation of sulfide in oxygen-saturated aqueous solutions is accelerated by dissolved or silica-bonded cobalt phthalocyanines. On the basis of thermodynamical considerations it is postulated that the catalyst enhances the formation of disulfide as the initial elementary reaction step. The following reaction steps are largely unaffected by the catalyst, as indicated by a product ratio sulfate/thiosulfate=0.86, comparable to that of the uncatalyzed autoxidation. A Langmuir-Hinshelwood formalism is developed for the catalytic reaction step and is demonstrated to fit best with the kinetics. In addition, from the kinetic data free enthalpies for the adsorption of HS^? (i) at the dissolved phthalocyanine (ΔG = ?17.6 kJ/mole) and (ii) at the immobilized complex (ΔG = ?20.0 kJ/mole) are calculated.     

Nonionic water‐soluble polymer: Preparation,characterization, and application of poly(1‐vinyl‐2‐pyrrolidone‐co‐hydroxyethylmethacrylate) as a polychelatogen

The free‐radical copolymerization of water‐soluble poly(1‐vinyl‐2‐pyrrolidone‐co‐hydroxyethylmethacrylate) was carried out with a feed monomer ratio of 75:25 mol %, and the total monomer concentration was 2.67M. The synthesis of the copolymer was carried out in dioxane at 70°C with benzoyl peroxide as the initiator. The copolymer composition was obtained with elemental analysis and ¹H‐NMR spectroscopy. The water‐soluble polymer was characterized with elemental analysis, Fourier transform infrared, ¹H‐ and ¹³C‐NMR spectroscopy, and thermal analysis. Additionally, viscosimetric measurements of the copolymer were performed. The thermal behavior of the copolymer and its complexes were investigated with differential scanning calorimetry (DSC) and thermogravimetry techniques under a nitrogen atmosphere. The copolymer showed high thermal stability and a glass transition in the DSC curves. The separation of various metal ions by the water‐soluble poly(1‐vinyl‐2‐pyrrolidone‐co‐hydroxyethylmethacrylate) reagent in the aqueous phase with liquid‐phase polymer‐based retention was investigated. The method was based on the retention of inorganic ions by this polymer in a membrane filtration cell and subsequent separation of low‐molar‐mass species from the polymer/metal‐ion complex formed. Poly(1‐vinyl‐2‐pyrrolidone‐co‐hydroxyethylmethacrylate) could bind metal ions such as Cr(III), Co(II), Zn(II), Ni(II), Cu(II), Cd(II), and Fe(III) in aqueous solutions at pHs 3, 5, and 7. The retention percentage for all the metal ions in the polymer was increased at pH 7, at which the maximum retention capacity could be observed. The interaction of inorganic ions with the hydrophilic polymer was determined as a function of the pH and filtration factor. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 100: 178–185, 2006     

Synthesis and characterization of poly(thiophen‐3‐yl acetic acid 4‐pyrrol‐1‐yl phenyl ester‐co‐N‐methylpyrrole) and its application in an electrochromic device

Copolymer of thiophen‐3‐yl acetic acid 4‐pyrrol‐1‐yl phenyl ester (TAPE) with N‐methylpyrrole (NMPy) was synthesized by potentiostatic electrochemical polymerization in acetonitrile–tetrabutylammonium tetrafluoroborate solvent–electrolyte couple. The chemical structures were confirmed via Fourier transform infrared spectroscopy (FTIR), cyclic voltammetry (CV), and UV–vis spectroscopy. Electrochromic and spectroelectrochemical properties of poly(TAPE‐co‐NMPy) [P(TAPE‐co‐NMPy)] were investigated. Results showed that the copolymer revealed color change between light yellow and green upon doping and dedoping of the copolymer, with a moderate switching time. Furthermore, as an application, dual‐type absorptive/transmissive polymer electrochromic device (ECD) based on poly(TAPE‐co‐NMPy) and poly(3,4‐ethylene dioxythiophene) (PEDOT) have been assembled, where spectroelectrochemistry, switching ability, stability, and optical memory of the ECD were investigated. Results showed that the device exhibited good optical memory and stability with moderate switching time. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 100: 1988–1994, 2006     

Novel alpha-7-oxy-4-(4-methoxyphenyl)-8-methylcoumarin substituted metal-free,Co(II) and Zn(II) phthalocyanines: Photochemistry,photophysics, conductance and electrochemistry

Novel alpha-substituted metal-free, Co(II) and Zn(II) phthalocyanines, bearing four 7-oxy-4-(4-methoxyphenyl)-8-methylcoumarin moieties were synthesized. The compounds were characterized by elemental analysis, IR, UV–vis, ¹H NMR, ¹³C NMR and MALDI-TOF mass spectroscopies. The Zn(II) phthalocyanine compound showed J-type aggregation in non-coordinating solvents. The photophysical and photochemical properties of these compounds were described in different solvents. Direct current conductivity measurements of the films of Co(II) and Zn(II) phthalocyanines as a function of temperature showed that these compounds are semiconductors with the activation energies within the range of 0.40–0.84 eV. The variation of alternating current conductivity of the films with frequency was found to be represented by the function σ_AC = Aω^s. The results indicated that charge transport mechanism of the films can be explained by hopping. The redox properties of the compounds were also examined in dimethylsulfoxide and dichloromethane by voltammetry and in situ spectroelectrochemistry. The compounds displayed metal and/or phthalocyanine ring-based reduction and oxidation processes. The electrochemistry of a phthalocyanine compound forming a J-aggregated species has been investigated. It was found that some redox couples of the Zn(II) compound in dichloromethane is split due to the equilibrium between its aggregated and non-aggregated species.