Phthalocyanine

In this paper, we have prepared peripherally tetra-({6-[3-(diethylamino)phenoxy]hexyl}oxy substituted cobalt(II), copper(II), manganese(III) phthalocyanines (3, 4, 5) and their water-soluble derivatives (3a, 4a, 5a). Then, in vitro α-glucosidase and cholinesterases inhibitory actions of the water-soluble 3a, 4a, 5a were examined using spectrophotometric methods. 4a had the highest inhibitory effects among the tested compounds against α-glucosidase due to IC50 values. 4a and 5a had 40 fold higher inhibitory effects than the positive control.

11p lyhuyenthu 31-01-2023 4 2   Download

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.

21p lyhuyenthu 31-01-2023 3 2   Download

A phthalocyanine–fluorescein conjugate was designed and prepared. Its photophysical properties (electronic absorption and fluorescence) were determined and compared with those of an analogous derivative functionalized by a simple triazole without chromophore. It is likely to be used as a theranostic agent in photodynamic therapy.

11p langthannam 29-12-2021 6 0   Download

New phthalocyanine compounds containing mixed-donor substituted macrocyclic groups were synthesized. The complexes of metal phthalocyanines 3–5 were prepared by the reaction of 2 to get dinitrile derivative complexes by means of the corresponding anhydrous metal salts. Structures of the new compounds were characterized by IR, 1H NMR, 13C NMR, elemental analysis, and MS spectral data.

11p langthannam 29-12-2021 6 0   Download

This paper reviews the history of phthalocyanines in Turkey. Phthalocyanines are chemical compounds that were accidently discovered nearly a century ago. The relevant research and articles have grown dramatically in Turkey since our first paper on them containing four [15]crown[5] published in 1986. The ball-type phthalocyanines were produced and published as a new concept in phthalocyanine chemistry for the first time by our group in Turkey in 2006. Unfortunately, with the exception of our work on this subject, almost no papers have been published in Turkey or in other countries since then.

20p langthannam 29-12-2021 11 0   Download

The recent advances in the synthesis of carborane and boronic ester-substituted tetrapyrroles (porphyrins, porphyrazines, and phthalocyanines) are reviewed together with their possible utilization as agents for photodynamic therapy (PDT) and boron neutron capture therapy of cancer (BNCT) as well as dual PDT/BNCT sensitizers.

30p langthannam 29-12-2021 1 0   Download

In this communication, encapsulation studies between metallosupramolecular capsule 1, formed by 2 subphthalocyanines (SubPcs) coordinated to 3 metallic centers, and phthalocyanine (Pc)-C60 fullerene conjugates 2–5 have been carried out. It was shown that the encapsulation of the C60 moiety by the SubPc cage occurred exclusively for dyads 2–4, whereas it was not observed in the case of triad 5. The rigidity of the linker between the Pc and the fullerene unit proved to have an important impact in the complex formation.

7p langthannam 29-12-2021 5 0   Download

Geometry optimizations and TD-DFT calculations have been carried out on series of fused-ring-expanded phthalonitriles, phthalocyanines, and aza-dipyrromethene boron difluoride (aza-BODIPY) dyes and trends in their optical and redox properties have been analyzed. The potential utility of fused-ring-expanded phthalocyanine and aza-BODIPY analogues for photodynamic therapy and near infrared region sensor applications is assessed on this basis.

14p langthannam 29-12-2021 7 0   Download

Density functional theory was employed to investigate a series of phthalocyanine derivatives, discovering the limitation when the expansion of the conjugated system was employed to improve the hyper-Rayleigh scattering response coefficient. Furthermore, an unusually C∞v -type octupolar population was found by electrostatic potential analysis. In addition, the dynamic and static hyper-Rayleigh scattering responses (βHRS) were simulated using the coupled perturbed density functional theory, showing an increasing dynamic βHRS value along with an increase in incident light energy.

10p langthannam 29-12-2021 4 0   Download

:In this paper, the synthesis and characterization of peripheral tetra-2-(2-ethyloxyethyloxy)ethyloxy substituted oxo-titanium phthalocyanines (TiOPcs) are reported. The reaction of 2,2,3,3-tetrafluoropropoxy substituted and [2-(2- ethoxyethoxy)ethoxy] substituted TiOPcs (1 and 3) with 4-[(6-hydroxyhexyl)oxy]benzene-1,2-diol as a strongly chelating oxygen donor ligand is described. Compounds 1a and 3a bearing the hydroxyl group as an axial ligand of the bulky group are converted into a thiol group (1c and 3c).

8p langthannam 29-12-2021 2 0   Download

The synthesis of novel, symmetrical, tetrasubstituted manganese phthalocyanine complexes bearing 4 hexylthio, 2’,3’,4’,5’,6’-pentafluorobenzyloxy, 2’,3’,5’,6’-tetrafluoro-4’-hexylthio-benzyloxy, and 2’,3’,5’,6’-tetrafluoro-4’- pentoxy-benzyloxy units is reported. The new compounds have been characterized by using elemental analyses and UV-Vis, FT-IR, and mass spectroscopic data. The electrochemical properties of the manganese phthalocyanine complexes were investigated by cyclic and square wave voltammetry and the nature of the observed redox processes was studied by spectroelectrochemistry.

9p langthannam 29-12-2021 5 0   Download

Metal-free phthalocyanine 3 and its metallophthalocyanine derivatives 4, 5, and 6 (M = Zn, Co, and Ni) substituted with four 21-membered pentathiadiaza macrocycles were synthesized and their structures identified by elemental analysis, IR, 1 H NMR, mass, and UV-Vis spectroscopy techniques. The aggregation properties of phthalocyanines 4, 5, and 6 were investigated in different solvents and at different concentrations of dimethylformamide.

10p langthannam 29-12-2021 3 0   Download

The synthesis of a 4-(2,2-diphenylethoxy)phthalonitrile (1) and its organosoluble free base (2), zinc(II) (3), nickel(II) (4), and cobalt(II) (5) phthalocyanine derivatives is presented in this work. The novel complexes were characterized by elemental analyses and spectral data such as infrared, nuclear magnetic resonance, ultraviolet visible, and mass data. General tendencies were described for photophysics (fluorescence) and photochemistry (photodegradation and singlet oxygen quantum yields) of the free base and zinc(II) phthalocyanine derivatives in dimethylformamide.

11p langthannam 29-12-2021 5 0   Download

The synthesis of novel, symmetrical, tetrasubstituted metallophthalocyanines (cobalt, zinc, and copper) bearing four 2-{[2-(dimethylamino)ethyl](methyl)amino} ethoxy units was reported. The dinitrile derivative was converted into the water-soluble quaternized product by its reaction with methyl iodide. The quaternized zinc phthalocyanine was obtained from the reaction of the water-soluble dinitrile derivative with zinc acetate. The structures of the newly synthesized molecules were proposed according to elemental analysis, 1 H NMR, FT-IR, and UV-Vis spectral data.

8p langthannam 29-12-2021 3 0   Download

The synthesis of novel zinc, cobalt, indium, and metal-free phthalocyanines carrying four 3-(4-phenyloxy)coumarins in the periphery/nonperiphery were prepared by cyclotetramerization of 3-[4-(3,4-dicyanophenyloxy)phenyl]coumarin (2)/3-[4-(2,3- dicyanophenyloxy)phenyl]coumarin (3). The novel chromogenic compounds were characterized by elemental analysis, 1 H NMR, mass spectra, F-IR, and UV-vis spectral data. The effects of the coumarin units on the zinc, indium, and metal-free phthalocyanine complexes (2a/3a, 2c/3c, 2d/3d) were also investigated.

16p langthannam 29-12-2021 9 0   Download

The thermal stabilities of the phthalocyanine compounds were determined by thermogravimetric analysis. For metal-free (2) and zinc (3) phthalocyanines, photochemical (photodegradation and singlet oxygen quantum yields) and photophysical (fluorescence quantum yields and fluorescence lifetimes) properties were analyzed in dimethylsulfoxide (DMSO). The cobalt (4) and copper (5) phthalocyanines were not evaluated for this purpose because of their paramagnetic behavior. The metal-free (2) and zinc (3) phthalocyanines’ fluorescence quenching behaviors were also investigated.

17p langthannam 29-12-2021 6 0   Download

New polymeric phthalocyanine moieties (M = 2H, Zn, Ni, Cu, and Co) were synthesized via polytetracyclomerization reaction of o-bis[3-(3,4-dicyanophenoxy)propyloxy]benzene (3), which can be obtained by the reaction of 4-nitrophthalonitrile with o-bis[(3-hydroxypropyl)oxy]benzene. Aggregation and disaggregation behavior of the polymeric phthalocyanine (5) was studied with some alkali and earth alkali metal cations. Measured intrinsic viscosities of the polymeric phthalocyanines exhibited a substantial decreasing tendency with dilution of the solution.

18p langthannam 29-12-2021 3 0   Download

The synthesis of tetraaminopropylamid substituted phthalocyanines was targeted to prepare enhanced soluble phthalocyanines in common solvents from hydrophobic to hydrophilic that bore nonionic groups on their periphery. Metal-free (H2Pc) and metallophthalocyanines (Zn(II) (ZnPc), Cu(II) (CuPc) and Co(II) (CoPc)) were prepared and characterized by UV-Vis, FT-IR, and mass spectroscopies. The 1 H NMR spectra were recorded for the diamagnetic phthalocyanine species H2Pc and ZnPc.

13p langthannam 29-12-2021 5 0   Download

In this study, new cobalt phthalocyanine containing a 2-(2-benzothiazolylthio)ethoxy group at peripheral positions has been synthesized and characterized by spectroscopic methods (IR, UV-Vis elemental analysis, and mass spectroscopies). Catalytic activity of Co(II) phthalocyanine has been investigated in the presence of oxidants such as tert-buthylhydroperoxide, m-chloroperoxybenzoic acid, and H2 O2 . Co(II) phthalocyanine shows catalytically activity and product conversion under mild conditions.

8p langthannam 29-12-2021 4 0   Download

The synthesis, characterization, and spectroscopic properties of novel nonperipherally tetrasubstituted metallophthalocyanines (zinc, cobalt, copper, manganese, and indium) bearing 4 (7-(trifluoromethyl)quinolin-4-yl)oxy units has been reported. The new compounds have been characterized using UV-Vis, IR, 1H NMR, 13C NMR, 19F NMR, and mass spectroscopic data. The absorption properties of these new complexes were compared to those of peripherally substituted phthalocyanine derivatives.

11p langthannam 29-12-2021 7 0   Download