Zinc Phthalocyanine Complexes Research Articles

Synthesis of zinc phthalocyanine complex containing tetra propanoic acid groups: Electronic properties and inhibitory effects on some metabolic enzymes

In the new study, first the synthesis and characterization of 2, 10, 16, 24-Tetrakis-3-(phenoxy) propanoic acid phthalocyaninato zinc (II)(4) and its starting compound are presented. The aggregation properties of compound (4) were investigated with the UV–visible spectrum, and the excitation and emission properties were investigated with the fluorescence spectra. The new compounds were characterized by IR, UV-visible, Mass and 1H NMR spectroscopy. These 3-(3,4-dicyanophenoxy) propanoic acid (3) and compound (4) had effective inhibition against α-glycosidase, α-amylase, butyrylcholinesterase and acetylcholinesterase. IC50 values were found as 4.21–6.57 µM for AChE, 0.32–1.88 µM for BChE, 47.14–62.07 µM for α-amylase, and 13.41–21.82 µM for α-glycosidase. By molecular docking study, compared to reference compounds (tacrine and acarbose) of compound (4) [-9.25 kcal/mol for AChE; -9.30 kcal/mol for BChE; -6.50 kcal/mol for α-amylase and -8.49 kcal/mol for α-glycosidase seem to be more effective and promising. Drug development for the treatment of diabetes, hyperglycemia, and obesity has as one of its design goals the creation of molecules that are α-amylase and α-glycosidase inhibitors. As a result, compound (4) can have promising anti Alzheimer drug potential and record as novel anti-diabetic inhibitors.

Synthesis of phenanthroline substituted five-nuclear phthalocyanine zinc complex and exploring of photochemical and sono-photochemical properties

Sono-photodynamic therapy (SPDT) which is the combination of photodynamic therapy (PDT) and sonodynamic therapy (SDT) is an alternative and efficient method among cancer treatments achieving high singlet oxygen quantum yield. This study aimed to synthesize Schiff base substituted Zn phthalocyanine containing phenanthroline group to obtain suitable sono-photosensitizer. The target phthalocyanine (4) was obtained by cyclotetramerization reaction of phenanthroline-Zn(II) complex substituted phthalonitrile (3) with zinc acetate. The synthesized compounds were characterized by various spectroscopic techniques including FT-IR, Mass, UV–Vis, and 1H NMR spectroscopy. The singlet oxygen quantum yield was calculated in both photochemical and sono-photochemical method for compound 4. While the ΦΔ value was calculated as 0.72 for photochemical method, the ΦΔ value reached to 0.98 for sono-photochemical method.

Several biological properties and synthesis of 2‐(4‐methylthiazol‐5‐yl) ethoxy substitute zinc phthalocyanine

In this study, 4‐(2‐(4‐methylthiazol‐5‐yl) ethoxy) phthalonitrile (3) and zinc phthalocyanine complex (4) were synthesized and characterized. UV–vis and fluorescence spectra, aggregation, and fluorescence parameters of the zinc phthalocyanine compound were investigated. As biological properties, DPPH radical capture, antidiabetic, DNA cutting, antimicrobial, photodynamic antimicrobial, anti‐biofilm activities, and microbial cell viability parameters of the compounds were determined. The highest antioxidant activity was found as 62.80% at 100 mg/L concentration with compound 4, and compound 4 also showed the best antidiabetic activity as 65.17% at 400 mg/L concentration. In DNA cutting activity, it was determined that 3 and 4 cut DNA at all concentrations. For compounds 3–4, the minimum inhibitory concentration (MIC) values were found to be 32 and 16 mg/L for Enterococcus hirae and Enterococcus feacalis, respectively. The strongest MIC value of photodynamic antimicrobial activity was achieved as 4 mg/L for E. feacalis with 4. It was observed that both compounds inhibited the microbial viability activity of Escherichia coli by 100% at concentrations of 100 mg/L. Compound 4 inhibited biofilms of Pseudomonas aureginosa and Staphylococcus aureus as 92.48% and 98.56% at 50 mg/L concentration, respectively.

The synthesis of novel water-soluble zinc (II) phthalocyanine based photosensitizers and exploring of photodynamic therapy activities on the PC3 cancer cell line.

In this study, Schiff base substituted phthalocyanine complexes (Zn1c, Zn2c) and their quaternized derivatives (Q-Zn1c, Q-Zn2c) were synthesized for the first time. Their structures have been characterized by FT-IR, 1H-NMR, UV-Vis, mass spectrometry and elemental analysis as well as. The photophysicochemical properties (fluorescence, singlet oxygen and photodegradation quantum yield) of these novel complexes were investigated in dimethylsulfoxide (DMSO) for both non-ionic and quaternized cationic phthalocyanine complexes and in aqueous solution for quaternized cationic phthalocyanine complexes. Water soluble cationic phthalocyanine compounds gave good singlet oxygen quantum yield (0.65 for Q-Zn1c, 0.66 for Q-Zn2c in DMSO; 0.65 for Q-Zn2c in aqueous solution). The binding of Q-Zn1c and Q-Zn2c to BSA/DNA was studied by using UV-Vis and fluorescence spectroscopy and these. Studies indicate that the mechanism of BSA quenching by quaternized zinc(II) phthalocyanines was static quenching. Quaternized zinc(II) phthalocyanines interacted with ct-DNA by intercalation. Quaternized zinc(II) phthalocyanines caused a decrease in cell viability and triggered apoptotic cell death after PDT was applied at a concentration that did not have a toxic effect on their own. Q-Zn1c and Q-Zn2c mediated PDT reduced the activity of SOD, CAT, GSH while increased MDA level in the prostate cancer cells. Furthermore, expression of apoptotic proteins after PDT was examined. The results revealed that the synthesized water soluble quaternized zinc(II) phthalocyanine complexes (Q-Zn1c and Q-Zn2c) are promising potential photosensitizers for PDT.

Comparison of the photochemical properties of phthalocyanine and hemiporphyrazine Zn(II) complexes

In DMF (dimethylformamide) solutions containing concentrations of (NEt4)Br (Et = ethyl) between 0.001 and 0.05 M both zinc phthalocyanine (Pc) and hemiporphyrazine (Hp) complexes are dissolved and form species [Zn(Hp)(Br)]–, and [Zn(Pc)(Br)]–. The increase in formation of the hemiporphyrazine bromide adduct is revealed by a linear dependence of the UV–Vis absorption spectrum on the Br– concentration whereas, over the same concentration range, absorption measurements indicate the formation of the phthalocyanine bromide adduct in solution. The x-ray and molecular structure of [NEt4][Zn(Pc)(Br)](H2O)0.33 has been determined showing the coordination of the Br– to the metal center. Photo-induced processes of the Zn complexes were investigated with deaerated solutions in a time scale t ≥10 ns. The 355 nm flash irradiation of [Zn(Hp)(Br)]– produced transient spectra which showed a bathochromic shift of the absorption maximum from 460 nm to 440 nm and an increase of the spectrum rate of decay with increasing Br– concentrations. The initial spectrum is attributed to the (nπ*–LLCTBr→Hp)[Zn(Hp)(Br)]– excited state which reacts with H-atom donors forming a radical [Zn(Hp-H)(Br)]•–. On the other hand, a transient spectrum, λmax ∼600 nm, grows in a time t ≤0.6 µs when [Zn(Pc)(Br)]– is flash irradiated at 355 nm. The photoreactions of these complexes with SCN– and 2-propanol (IPA) were studied. Despite of the apparent similarity between both complexes, IPA was photo-oxidized by both complexes although by different mechanisms, an electron transfer with [Zn(Pc)(Br)]– and an H atom abstraction with [Zn(Hp)(Br)]–. The photo-oxidation of SCN– by [Zn(Pc)(Br)]– but not by [Zn(Hp)(Br)]– makes a remarkable difference between the photochemistries of these complexes.

Farklı Kalkon, Ftalonitril ve Periferal Tetra Çinko Ftalosiyanin Türevlerinin In Vitro Layşmanyasidal Aktivitesi

In this study, in vitro leishmanicidal activity of different chalcone compounds (5-8), phthalonitrile derivatives (5a-8a), and zinc phthalocyanine (5b-8b) complexes bearing chalcone compound in peripheral positions were investigated. Phthalonitrile derivatives were obtained in the reaction of 4-nitrophthalonitrile with chalcone compound obtained by the reaction of acetophenone and various aldehydes. Zinc phthalocyanine complexes containing chalcone in the peripheral position were obtained as a result of the reaction of the synthesized phthalonitrile derivative with Zn(CH₃COO)₂ metal salt. The characterization of the synthesized original compounds (8, 8a and 8b) was performed by various spectroscopic methods (IR, 1H and 13C NMR, MALDI-TOF-MS and UV-Vis). Leishmaniasis is a disease lead to by parasites of the genus Leishmania, which can result in death as well as various clinical syndromes, generally in developing countries. New drug studies are needed because the drugs used in the treatment are toxic and resistance develops against them. In this study, the leishmaniacidal activities of synthesized chalcone, phthalonitrile and phthalocyanine series substances against Leishmania infantum and Leishmania major parasites were evaluated for the first time.

Asymmetrical zinc phthalocyanine conjugated to various nanomaterials for applications in phototransformation of organic pollutants and photoinactivation of bacteria

Zinc phthalocyanine (ZnPc) complexes are linked to metallic nanoparticles covalently via amide and ester bonds. The photocatalytic activity of the conjugates of ZnPc complexes with NiWO4, Ag2WO4, CoWO4 and Ag-Fe3O4 nanoparticles are evaluated for photodegradation of methylene blue, tetracycline, and dibenzothiophene. The photocatalytic efficiencies of the prepared phthalocyanine complexes increased in the presence of nanoparticles. This work also reports on the photodynamic antimicrobial chemotherapy activity of these materials against Staphylococcus aureus (S. aureus) bacteria. The results indicate that Ag2WO4 based nanoconjugates exhibit high antimicrobial activity with higher log reduction compared to NiWO4, CoWO4 and Ag-Fe3O4 based materials.

Zinc(II) phthalocyanine substituted by sulfonamide derivative: Photophysical and photochemical properties

Synthesis of two different new compounds, (E)-4-((2‑hydroxy-3‑methoxy-5-nitro benzylidene)amino)-N-(pyridine-2-yl)benzenesulfonamide 1, (E)-4-((2-(3,4-dicyanophenoxy )-3‑methoxy-5-nitrobenzylidene)amino)-N-(pyridine-2-yl)benzenesulfonamide2and 2(3),9(10),16(17),23(24)-tetrakis-[(E)-4-((3‑methoxy-5-nitro-2-(λ1-oxidanyl)benzylidene) amino)-N-(pyridine-2-yl)benzene sulfonamid] zinc(II) phthalocyanine complex 3 was carried out. Their structures were characterized by spectroscopic methods such as Fourier transform infrared, Proton nuclear magnetic resonance, Carbon-13 nuclear magnetic resonance, Ultraviolet-visible, Fluorescence, Matrix-assisted laser desorption/ionization, Time-of-flight mass (except compounds 1 and 2), as well as Elemental analysis. The spectroscopic, photophysical, and photochemical properties of zinc(II) phthalocyanine complex 3, substituted with new benzenesulfonamide derivatives containing different functional groups, were explored in dimethylsulfoxide to determine its usability as a photosensitizer for photodynamic therapy. The effects of the presence of tetra-substituted new benzenesulfonamide groups from the peripheral positions of the zinc(II) phthalocyanine ring on the spectroscopic, photophysical, and photochemical properties were investigated and these properties were compared with the properties of the substituted and unsubstituted zinc(II) phthalocyanines. As a photosensitizer for photodynamic therapy, this new phthalocyanine 3 has well solubility in different kinds of solvents without aggregation sufficient fluorescence properties, ability to produce singlet oxygen, and photostability under appropriate light irradiation.

Zinc(II), Palladium(II), and Metal-Free Phthalocyanines Bearing Nipagin-Functionalized Substituents against Candida auris and Selected Multidrug-Resistant Microbes.

Due to the rapidly increasing problem of antibiotic resistance in recent years, the use of phthalocyanines as photosensitizers with their superior properties in photodynamic antimicrobial therapy (PACT) applications has become important. In this study, magnesium(II) 1,4,8,11,15,18,22,25-octakis(4-[4-butoxycarbonylphenoxy]butyloxy)phthalocyanine was used in the demetalation reaction in trifluoroacetic acid, and subsequently subjected to metalation reaction in dimethylformamide with zinc(II) acetate and bis(benzonitrile)palladium(II) chloride towards zinc(II) and palladium(II) derivatives. Three phthalocyanines, including a demetalated one as well as two metalated, in the core with zinc(II) and palladium(II) were characterized using 1D and 2D NMR spectroscopy and mass spectrometry. In addition, all macrocycles were subjected to absorption and emission studies as well as photostability tests. In a photochemical study, zinc(II) and palladium(II) phthalocyanine complexes appeared to be efficient singlet oxygen generators. There were noted quantum yields of singlet oxygen generation for zinc(II) phthalocyanine derivative in DMF and DMSO at 0.55 and 0.72, whereas for palladium(II) complex at 0.73 and 0.77, respectively. Liposomal formulations of phthalocyanine derivatives were prepared, and their activity was evaluated against a broad spectrum of antibiotic-resistant microorganisms, such as methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli (ESBL+), Candida albicans resistant to fluconazole, C. auris, and against dermatophytes. Phthalocyanine palladium(II) complex showed the highest bactericidal activity against all antibiotic-resistant microorganisms, including reducing C. auris growth at 3.54 log.

Physical–chemical studies of new, versatile carbazole derivatives and zinc complexes: Their synthesis, investigation of in vitro inhibitory effects on α‐glucosidase and human erythrocyte carbonic anhydrase I and II isoenzymes

In this study, two novel zinc–phthalocyanine complexes (4a and 6a), containing carbazole rings, were investigated. The first phthalocyanine 4a has been synthesized from 4‐(2‐(3‐acetyl‐9H‐carbazol‐9‐yl)ethoxy at the peripheral position. Likewise, the second phthalocyanine 6a has been synthesized from 4‐(2‐(3‐cinnamoyl‐9H‐carbazol‐9‐yl)ethoxy at the same position. The new phthalocyanines (Pcs) and their ligands are soluble in organic solvents, such as dimethylformamide, dimethyl sulfoxide, dichloromethane, ethyl acetate, and methanol/ethanol. The Zn (II) complexes were characterized by Fourier transform infrared spectroscopy, nuclear magnetic resonance (NMR) (except 13C NMR for complexes), elemental analysis, mass spectrometry, and UV–Vis spectroscopy. Also, photophysical and photochemical properties and cyclic voltammogram for the N‐substituted carbazole zinc–Pcs have been reported. The evaluation of carbazole Zn (II) complexes (4a and 6a) and ligands (3, 4, 5, and 6) for in vitro α‐glucosidase inhibitory activities was performed compared to standard drugs acarbose, and kinetic studies were also carried out to determine their inhibition modes. The inhibitory effects of these new Pcs (4a and 6a) and their ligands (3, 4, 5, and 6) on human erythrocytes carbonic anhydrase I (hCA I) and II (hCA II) isoenzymes were investigated. Moreover, in silico studies were also carried out to better investigate the interactions of N‐substituted carbazole containing zinc Pcs with the active sites of hCA I and II isoforms.

Synthesis, theoretical DFT analysis, photophysical and photochemical properties of a new zinc phthalocyanine compound

In this study, fluorescent zinc phthalocyanine compound was synthesized using 4-(2-(4-(2-phenylpropan-2-yl) phenoxy) phenoxy) phthalonitrile and zinc metal salt. The structure of compounds was characterized by using 1H, and 13C NMR, FT-IR, Mass, UV-Vis spectroscopy. The fluorescence emission, excitation and absorption properties of this phthalocyanine compound were studied in tetrahydrofuran and DMSO. Aggregation behaviors for different concentrations in the same solvent were investigated. Quantum chemical calculations were performed using 6-311G basis set of DFT (B3LYP and CAMB3LYP) methods. The structural optimization, molecular orbital analysis, and electronic properties of the synthesized phthalocyanine were then determined in the ground state and gas phase of the DFT method. Moreover, molecular electrostatic potential (MEP) maps were drawn to identify the reactive regions of the zinc phthalocyanine complex. The data of the study show that the phthalocyanine complex can be used as sensor agent for biological fluorescence analysis.

Schiff base containing pyridine groups functionalized water-soluble phthalocyanine: Synthesis, photo-physicochemical properties, and bovine serum albumin binding behavior.

The novel pyridine bearing schiff base substituted metal-free (9), zinc(II) phthalocyanine (10), and its quaternized derivative (11) were designed and synthesized. These phthalocyanines were fully characterized by spectroscopic methods (FT-IR, UV-Vis, MALDI-TOF, and 1H NMR). The photo-physicochemical properties of these phthalocyanines were investigated in both DMSO and DMF for 10 and in both DMSO and aqueous solution for 11. The addition of pyridine bearing Schiff base groups as peripheral ligands showed an improvement in the photophysical and photochemical properties. In addition, a spectroscopic investigation of the binding behavior of the water-soluble zinc (II) phthalocyanine complex to bovine serum albumin (BSA) was also studied in this work.

Non-aggregating zinc phthalocyanine sensitizer with bulky diphenylphenoxy donor groups and pyrazole-3-carboxylic acid anchoring group for coadsorbent-free dye-sensitized solar cells

A novel unsymmetrical zinc phthalocyanine complex (PCA-ZnPc-3) containing six 2,6-diphenylphenoxy donor groups and pyrazole-3-carboxylic acid anchoring group has been synthesized and used as a sensitizer for dye-sensitized solar cells (DSSCs). The optical, electrochemical and photovoltaic characteristics were evaluated and compared with the dyes containing the same anchoring group and tert-butyl (PCA-ZnPc-1) or hexylsulfanyl (PCA-ZnPc-2) donor groups, developed by our group. The DSSC with PCA-ZnPc-3 exhibited a higher power conversion efficiency (PCE) of 2.04% as compared to that of PCA-ZnPc-1 (PCE = 1.74%) and PCA-ZnPc-2 (PCE = 1.89%). This enhancement in efficiency may be ascribed to the less dye aggregation and appropriate dye coverage. These results suggest that the incorporation of 2,6-diphenylphenoxy into pyrazole-3-carboxylic acid-based zinc phthalocyanine sensitizers can improve photovoltaic performance of DSSCs.

Asymmetrical zinc(II) phthalocyanines cobalt tungstate nanomaterial conjugates for photodegradation of methylene blue

Herein, we present syntheses of three asymmetrical zinc(II) phthalocyanine (ZnPc) complexes and hydrothermal synthesis of cobalt tungstate nanoparticles. The ZnPc derivatives were covalently linked to cobalt tungstate nanoparticles. Photophysical and photochemical behaviour of Pcs and nanoconjugates were investigated. The nanoconjugates generated higher triplet quantum yield and singlet oxygen quantum yield than the ZnPcs alone. Furthermore, in this paper photocatalytic efficiencies of ZnPc complexes and nanoconjugates were investigated for the degradation of methylene blue and higher photocatalytic behaviour was observed for the conjugates. The kinetic model was used to study photocatalytic behaviour of all the prepared photocatalysts.

Preferential Formation of Side‐Pocket‐Substituted Zinc Phthalocyanines Emitting Beyond 800 nm

AbstractA series of zinc (1,4,8,11,15,18,22,25‐octabutoxy)phthalocyanine (2) complexes that spontaneously form 5‐coordinate complexes with anionic axial ligands neutralized with side‐pocket cations, of the form Cation‐PcZnX (X=Cl, OAc; Cation=H+ or Li+), was synthesized and structurally characterized. The side‐pocket protonation of the axial‐chloride species pushed the emission maximum from 760 nm (for axial ligand‐free 2) to 826 nm, well into the NIR region. A 1D‐coordinated chain bridged by lithium and chloride atoms was isolated and structurally characterized, representing the first side‐pocket metalated PcM species. This preferential formation of axially substituted [PcZnX]− “ate” complexes and their sequestration of both protons and lithium cations, opens a new series of materials with unique structural and electronic properties. Furthermore, their ability to both absorb and emit in the NIR region makes them desirable for numerous applications.

Sensing Behavior of Metal-Free Porphyrin and Zinc Phthalocyanine Thin Film towards Xylene-Styrene and HCl Vapors in Planar Optical Waveguide.

The sensing behavior of a thin film composed of metal-free 5, 10, 15, 20-tetrakis (p-hydroxy phenyl) porphyrin and zinc phthalocyanine complex towards m-xylene, styrene, and HCl vapors in a homemade planar optical waveguide (POWG), was studied at room temperature. The thin film was deposited on the surface of potassium ion-exchanged glass substrate, using vacuum spin-coating method, and a semiconductor laser light (532 nm) as the guiding light. Opto-chemical changes of the film exposing with hydrochloric gas, m-xylene, and styrene vapor, were analyzed firstly with UV-Vis spectroscopy. The fabricated POWG shows good correlation between gas exposure response and absorbance change within the gas concentration range 10–1500 ppm. The limit of detection calculated from the logarithmic calibration curve was proved to be 11.47, 21.08, and 14.07 ppm, for HCl gas, m-xylene, and styrene vapors, respectively. It is interesting to find that the film can be recovered to the initial state with trimethylamine vapors after m-xylene, styrene exposures as well as HCl exposure. The gas-film interaction mechanism was discussed considering protonation and π-π stacking with planar aromatic analyte molecules.

Study of Cytotoxic and Photodynamic Activities of Dyads Composed of a Zinc Phthalocyanine Appended to an Organotin.

The combination of photodynamic therapy and chemotherapy is a promising strategy to enhance cancer therapeutic efficacy and reduce drug resistance. In this study two zinc(II) phthalocyanine-tin(IV) conjugates linked by a triethylene glycol chain were synthesized and characterized. In these complexes, the zinc(II) phthalocyanine was used as a potential photosensitizer for PDT and the tin complex was selected as cytostatic moiety. The two dyads composed of zinc(II) phthalocyanine and tin complexes exhibited high cytotoxicity, in absence of light stimulation, against MCF-7 human breast cancer cells with low LC50 values in the range of 0.016–0.453 µM. In addition, these complexes showed superior cytotoxicity than their mixture of equimolar component, accompanied with a higher activity towards cancer cells compared to human healthy fibroblasts. However, under irradiation of the zinc phthalocyanine unit (at 650 nm) no photodynamic activity could be detected, due to the most likely quenching of zinc(II) phthalocyanine singlet excited state by the nearby tin complex according to a photoinduced electron transfer process. This study demonstrates the potential of heterometallic anticancer chemotherapeutics composed of a zinc phthalocyanine and tin complex, and it highlights that the development of such conjugates requires that the sensitizer preserves its photophysical properties and in particular its singlet oxygen sensitization ability in the conjugate in order to combine the PDT activity with the cytotoxicity of the anticancer drug.

Peripherally octamethyl zinc(II) phthalocyanines with various axial substituents

A series of zinc(II) phthalocyanine complexes peripherally octa-substituted by methyl groups and with axially ligated N-donor ligands, (Zn(Me)8Pc-L, where L is pyridine (4), 3-methylpyridine (5), 3,4-lutidine (6) and 3,5-lutidine (7)), was synthesized. All the Zn(Me)8Pc-L complexes 4–7 were obtained in the crystalline form, suitable for X-ray single crystal analysis. The effect of the peripheral substituents as well as the ligation effect of the axial ligands on the structure were analyzed. In all the here studied zinc(II) phthalocyanine derivatives, the interaction of the metal center with the N atom of the axial ligand results in its displacement by ~ 0.4 Å from the N4-isoindole plane of phthalocyaninate macrocycle that adopts a saucer-shaped form. The X-ray geometry and stereochemistry of the zinc(II) phthalocyanine derivatives were compared with that obtained by DFT methods. Analysis of the Hirshfeld's surface shows a reduction of the π···π interactions with the simultaneous increase of the CH···N, CH···N, H···H and CH··· π interactions in the investigated complexes 4–7. Partial MO energy diagrams and the calculated absorption spectra of the Zn(Me)8Pc-L derivatives 4–7 exhibit a bathochromic shift of the maximum absorption wavelength (λmax) in comparison with the spectrum of Zn(Me)8Pc by about 20 nm. Complexes 4–7 have a strong absorption band in the therapeutic window (600–900 nm) and the HOMO-LUMO energy gap is sufficient to excite the ground state of oxygen and therefore they can be tested as potential photosensitizers for PDT.

Ultrathin Langmuir–Schaefer films of slipped-cofacial J-type phthalocyanine dimer: Supramolecular organization, UV/Vis/NIR study and nonlinear absorbance of femtosecond laser radiation

Based on a comprehensive theoretical and experimental approach, a low-defect thin film of stable dimeric phthalocyanine zinc complex (bis-[2-hydroxy-9(10),16(17), 23(24)-tri-tert-butylphthalocyanine]zinc – J-[OHPctZn]2) was prepared. It is shown that the dye forms stable amorphous edge-on monolayers at the air/water interface with an insignificant content of cylindrical 3D aggregates. These floating layers keep their structure when transferred by the Langmuir-Schaefer method onto a solid substrate, demonstrating a tendency towards ordered H-aggregation with preserving their linear molecular properties. Mixed two- and three-photon absorption of femtosecond laser pulses (280 fs) was firstly detected on this sample, as well as the ability of a material to the nonlinear attenuation of the intense irradiation, which is important for optical limiting.

Photosensitive field effect transistor based on metallo-phthalocyanines containing (4-pentylphenyl) ethynyl moieties

The syntheses of new cobalt, manganese and zinc phthalocyanine complexes containing 4-pentylphenylethynyl substituents at the peripheral positions are reported. 4-[(4-pentylphenyl) ethynyl] phthalonitrile was obtained through Sonogashira coupling reaction. The new compounds have been characterized using UV–vis, FT- IR, 1H NMR, 13C NMR, and mass spectroscopy data. In order to study the dependence of device performance on the central metal atom, photosensitive field effect transistor based on tetra-substituted metallo phthalocyanines with [(4-pentylphenyl) ethynyl groups at peripheral positions were fabricated and characterized. Photoelectric characterization results showed that the device with active layer of 3 exhibits highest photoelectric performance with maximum field effect mobility (4.27 ×10-3 cm2/Vs), photosensitivity (72.05), and photo/dark current ratio (230). It was found that the photoelectric performance of the Pc compounds depends on the central metal atom which is found consistent with UV–vis spectrum. Surface topography of the sensing films were analyzed by atomic force microscopy.