Bis-indole substituted phthalocyanines: Photophysical and photochemical properties

2020 ◽  
Vol 25 (01) ◽  
pp. 66-74
Author(s):  
Kevser Harmandar ◽  
Esra N. Kaya ◽  
Mehmet F. Saglam ◽  
Ibrahim F. Sengul ◽  
Devrim Atilla
Keyword(s):  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Spectral Data ◽  
Quantum Yields ◽  
Oxygen Generation ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Singlet Oxygen Generation ◽  
Photochemical Properties ◽  
C Nmr

Tetra substituted peripheral and non-peripheral Zn(II) phthalocyanines were successfully synthesized employing 4-(bis(3-methyl-1H-indol-2-yl)methyl)phenol as a starting material. The structure of these synthesized compounds was confirmed using 1H NMR, [Formula: see text]C NMR, infrared (IR), UV-vis, and MALDI-TOF spectral data. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation) properties of all synthesized peripheral and non-peripheral compounds were investigated in order to determine the potential of these compounds for application in photodynamic therapy.

Novel carboxylic acid terminated silicon(IV) and zinc(II) phthalocyanine photosensitizers: Synthesis, photophysical and photochemical studies

2018 ◽  
Vol 22 (11) ◽  
pp. 1010-1021 ◽  
Author(s):  
Arif Hışır ◽  
Gülşah Gümrükcü Köse ◽  
Göknur Yaşa Atmaca ◽  
Ali Erdoğmuş ◽  
Gülnur Keser Karaoğlan
Keyword(s):  
Carboxylic Acid ◽  
Singlet Oxygen ◽  
Quantum Yields ◽  
Cooh Group ◽  
Experimental Conditions ◽  
Oxygen Generation ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Silicon Phthalocyanines ◽  
Photochemical Properties

In order to improve the efficacy of photochemical properties for photodynamic therapy (PDT) applications, carboxylic acid groups axially conjugated with silicon(IV) and at the peripheral position with zinc(II) phthalocyanine skeletons for new photosensitizers to investigate the influence of the COOH group positions on the photophysicochemical performance are described in this study. Silicon (IV) (3 and 5) and zinc (II) (7) phthalocyanines were characterized by UV-vis, FTIR, 1H-NMR, MALDI-TOF MS and elemental analysis spectral data. Furthermore, the photophysical (fluorescence quantum yields and fluorescence quenching studies), photochemical (photodegradation and singlet oxygen generation) and aggregation properties of the newly synthesized phthalocyanines were investigated in dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) solutions. The results were compared with that of zinc and silicon phthalocyanines. Singlet oxygen quantum yields ranged from 0.23 to 0.63 via Type II mechanism under the experimental conditions studied. The fluorescence of the phthalocyanine complexes (3, 5 and 7) is effectively quenched by 1,4-benzoquinone (BQ) in DMSO, DMF and THF.

New peripherally substituted lutetium mono and bis phthalocyanines: Synthesis and comparative photophysical and photochemical properties

2019 ◽  
Vol 23 (11n12) ◽  
pp. 1542-1550
Author(s):  
Nagihan Kocaağa ◽  
Öznur Dülger Kutlu ◽  
Ali Erdoğmuş
Keyword(s):  
Mass Spectrometry ◽  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Photophysical Properties ◽  
Quantum Yields ◽  
Synthesis And Characterization ◽  
Type Ii ◽  
H Nmr ◽  
Photochemical Properties

In this study, the synthesis and characterization of mono-(phthalocyaninato) lutetium(III) (1-Cl and 1-F) [Lu[Formula: see text](AcO)(Pc)] (Pc [Formula: see text] phthalocyaninato, AcO [Formula: see text] acetate) and bis-(phthalocyaninato) lutetium(III) (2-Cl and 2-Br) [Lu[Formula: see text]Pc[Formula: see text]] bearing halogenated (F, Cl and Br) phenoxy–phenoxy groups are described and verified by IR, [Formula: see text]H-NMR, UV-vis and mass spectrometry. Photochemical and photophysical properties of 1-F, 1-Cl 2-Cl and 2-Br in DMSO are also presented. A comparison between photophysical and photochemical parameters of mono and bis derivatives showed that mono phthalocyanines are better photosensitizers than bis phthalocyanines. Photophysical and photochemical properties of phthalocyanines are very useful for photodynamic therapy applications. Singlet oxygen quantum yields [Formula: see text] give an indication of the potential of the complexes as photosensitizers in photodynamic therapy applications. The chloro, fluoro, bromo-phenoxy–phenoxy substituted mono-(phthalocyaninato) lutetium(III) complexes (1-Cl and 1-F) gave good singlet oxygen quantum yields (from 0.86 to 0.80) in DMSO. Thus, these complexes show potential as Type II photosensitizers for PDT of cancer.

Synthesis, characterization, photophysicochemical properties and theoretical study of novel zinc phthalocyanine containing four tetrathia macrocycles

2018 ◽  
Vol 22 (01n03) ◽  
pp. 77-87 ◽  
Author(s):  
Mohamad Albakour ◽  
Gülenay Tunç ◽  
Büşra Akyol ◽  
Sinem Tuncel Kostakoğlu ◽  
Savaş Berber ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Zinc Phthalocyanine ◽  
Quantum Yields ◽  
Energy Structure ◽  
Fluorescence Measurement ◽  
Oxygen Generation ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Ft Ir ◽  
Phthalocyanine Derivative

In this work, Zn(II) phthalocyanine derivative (TTU-Pc) bearing 13-membered tetrathia macrocycles was synthesized, and the novel Zn(II) phthalocyanine derivative was fully characterized by elemental analysis and general spectroscopic methods such as MALDI-TOF mass, FT-IR, UV-vis and [Formula: see text]H-NMR. The synthesized phthalocyanine derivative has quite limited solubility in most of the common organic solvents. Fluorescence measurement was conducted for this Zn(II)phthalocyanine to estimate its fluorescence quantum yields. The singlet oxygen generation ability was also examined to investigate its photosensitizer properties. General trends were described for quantum yields of fluorescence, photodegradation and singlet oxygen quantum yields of this compound. The electrochemical properties of the molecule were investigated by cyclic voltammetry (CV) and square wave voltammetry (SWV). In addition, the lowest energy structure, the electronic structure and frontier molecular orbitals were calculated in DFT and the excitation spectrum was obtained by TDDFT calculations. We found that our computational and experimental results were in agreement.

Photophysical and photochemical properties of fluoroether-substituted zinc(II) and titanium(IV) phthalocyanines

2018 ◽  
Vol 22 (01n03) ◽  
pp. 46-55 ◽  
Author(s):  
İlke Gürol ◽  
Gülay Gümüş ◽  
Deniz Kutlu Tarakci ◽  
Ömer Güngör ◽  
Mahmut Durmuş ◽  
...  
Keyword(s):  
Quantum Yields ◽  
Central Metal Atom ◽  
Spectroscopic Techniques ◽  
Central Metal ◽  
Oxygen Generation ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Photochemical Properties ◽  
First Time

The synthesis and characterization of novel zinc(II) (1a–4a) and oxo-titanium(IV) (1b–4b) phthalocyanine derivatives bearing 1H,1H-nona?uoro-3,6-dioxaheptan-1-ol groups are described for the first time. These phthalocyanines (1a–4a and 1b–4b) were characterized by elemental analysis and different spectroscopic techniques such as UV-vis, [Formula: see text]H NMR, FTIR and mass. Furthermore, the photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation) properties of these phthalocyanines were investigated in tetrahydrofuran (THF) solution. The influence of the number of the substituted groups (tetra or octa), position of the substituents (peripheral or non-peripheral) and central metal atom (zinc or titanium) on the photophysical and photochemical properties of these phthalocyanines were evaluated.

Photochemical properties of substituted tetraazachlorins

2014 ◽  
Vol 18 (06) ◽  
pp. 457-464 ◽  
Author(s):  
Anton P. Lastovoy ◽  
Nina A. Kuznetsova ◽  
Ludmila K. Slivka ◽  
Elena A. Makarova
Keyword(s):  
Singlet Oxygen ◽  
Colloidal Solution ◽  
Quantum Yields ◽  
Aromatic Rings ◽  
Oxygen Generation ◽  
Singlet Oxygen Generation ◽  
Micelle Core ◽  
Photodegradation Mechanism ◽  
Photochemical Properties ◽  
Aqueous Micellar Solutions

The photochemical properties of water-insoluble metal-free tetraazachlorin derivatives in organic solvents and aqueous micellar solutions of nonionic surfactants were investigated. The quantum yields of fluorescence, singlet oxygen generation and photodegradation were evaluated in benzene. The highest photostability and singlet oxygen quantum yield (ΦΔ = 0.7) was found for 2,2,3,3-tetramethyl-7,8,12,13,17,18-hexaphenyltetraazachlorin. The moderate ΦΔ values (0.21–0.35) of triarenotetraazachlorins in benzene were established. Expansion of tetraazachlorin π-system by fusion of three aromatic rings leads to reduction of efficiency of singlet oxygen generation. The study of photodegradation mechanism shows that radical photooxidation apparently is most plausible, though 1 O 2 may partly contribute to photodestruction of some tetraazachlorins. In aqueous colloidal solution of nonionic surfactant (Cremophor EL) the same, as in benzene, effect of sensitizer structure upon efficacy of singlet oxygen production was observed. It was shown that 1 O 2 diffusion from micelle core into solution and then to target slows its oxidation rate substantially in comparison to the case where sensitizer and target are localized in the same micelle.

scholarly journals Novel Hexadeca-Substituted Metal Free and Zinc(II) Phthalocyanines; Design, Synthesis and Photophysicochemical Properties

Molecules ◽  
2018 ◽  
Vol 24 (1) ◽  
pp. 77 ◽  
Author(s):  
Ayoub Awaji ◽  
Baybars Köksoy ◽  
Mahmut Durmuş ◽  
Ateyatallah Aljuhani ◽  
Shaya Alraqa
Keyword(s):  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
13C Nmr ◽  
Design Synthesis ◽  
Oxygen Generation ◽  
Metal Free ◽  
Singlet Oxygen Generation ◽  
Ft Ir ◽  
Photochemical Properties ◽  
Phthalocyanine Derivative

The syntheses of a novel 1,4,8,11,15,18,22,25-octahexyloxy-2,3,9,10,16,17,23,24-octa-(4-trifluoromethoxyphenyl) phthalocyanine (3a) and its zinc(II) phthalocyanine derivative (3b) have been described and characterized by elemental analysis,1H NMR, 13C NMR, 19F NMR, mass, UV-Vis and FT-IR. The newly prepared metal-free phthalocyanine and its zinc(II) counterpart are soluble in most organic solvents. The photophysical and photochemical properties such as aggregation, fluorescence, singlet oxygen generation and photodegradation under light irradiation of these phthalocyanines have been investigated in DMF. The hexadeca-substituted phthalocyanines (3a and 3b) showed longer absorption and emission wavelength values when compared to that of reported phthalocyanine derivatives due to substitution of the all possible positions in the phthalocyanine framework. The zinc(II) phthalocyanine derivative does not only have a good singlet oxygen generation but also has other photophysicochemical properties that enables this phthalocyanine to be useful as a photosensitizer for cancer treatment using photodynamic therapy.

Silicon(IV) phthalocyanine-biotin conjugates: Synthesis, photophysicochemical properties and in vitro biological activity for photodynamic therapy

2017 ◽  
Vol 21 (07n08) ◽  
pp. 547-554 ◽  
Author(s):  
Asuman Dakoğlu Gülmez ◽  
Meltem Göksel ◽  
Mahmut Durmuş
Keyword(s):  
Photodynamic Therapy ◽  
Quantum Yields ◽  
Spectroscopic Techniques ◽  
Oxygen Generation ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Ft Ir ◽  
Human Cervical Cancer ◽  
Phthalocyanine Ring

Silicon (IV) phthalocyanines bearing one or two biotin groups on the axially positions were synthesized, and these novel phthalocyanines were characterized by elemental analysis and standard spectroscopic techniques such as FT-IR, [Formula: see text]H NMR, UV-vis and MALDI-TOF. The synthesized compounds are the first examples of axially biotin substituted silicon (IV) phthalocyanines. These phthalocyanines were designed as targeting photosensitizers for the treatment of cancer by photodynamic therapy (PDT) technique. The phthalocyanine ring was selected for its photosensitizer ability and the biotin group was selected as a targeting agent for increasing accumulation of these photosensitizers in tumor cells. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation) properties of the target silicon(IV) phthalocyanines were investigated in DMSO. The photosensitizing efficiency of the studied phthalocyanines was tested against human cervical cancer (HeLa) cells at different photosensitizer concentrations. Both axially mono- and bis-biotin substituted silicon(IV) phthalocyanines present high photocytotoxicity against HeLa cancer cells with the cell survival degree ranging from 13% to 50%. The photosensitivity and the intensity of damage were found to be directly related to the concentration of the used photosensitizers. According to the obtained results, both silicon(IV) phthalocyanine derivatives could be promising as photosensitizers for treatment of cancer by PDT technique.

Photophysical and photochemical properties of novel phthalocyanines bearing non-peripherally substituted mercaptoquinoline moiety

2012 ◽  
Vol 16 (07n08) ◽  
pp. 845-854 ◽  
Author(s):  
Göknur Yaşa ◽  
Ali Erdoğmuş ◽  
Ahmet Lütfi Uğur ◽  
M. Kasım Şener ◽  
Ulvi Avcıata ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Electronic Spectroscopy ◽  
Quantum Yields ◽  
Solubility In Water ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Good Solubility ◽  
Ft Ir ◽  
Photochemical Properties ◽  
First Time

The synthesis, photophysical and photochemical properties of nonperipherally (α) mercaptoquinoline substituted Zn(II) , TiO(IV) and Mg(II) and quaternized Zn(II) phthalocyanines are described for the first time. These complexes (2 to 5) and their precursor are characterized by elemental analysis, FT-IR, 1H NMR, electronic spectroscopy as well as mass spectroscopy. Complexes 2, 4 and 5 have good solubility in organic solvents such as CHCl3 , DCM, DMSO, DMF, THF and toluene and are not aggregated in all solvents within a wide concentration range. Complex 3 showed very good solubility in water as well as DMSO and DMF. General trends are described for singlet oxygen, photodegradation and fluorescence quantum yields of these complexes in DMSO and DMF. While complex 2 has higher singlet oxygen and fluorescence quantum yields than 3, 4 and 5, complex 4 has higher fluorescence quantum yields in DMF and DMSO than 2, 3 and 5. The effect of the solvents and metal on the photophysical and photochemical parameters of the metallophthalocyanines are also reported.

Zinc(II) complexes of tetrakis-(6,7-quinoxalino)porphyrazine bearing externally appended 2-pyridyl rings: Synthesis, UV-visible spectral behavior and photoactivity for singlet oxygen generation

2014 ◽  
Vol 18 (10n11) ◽  
pp. 1042-1050 ◽  
Author(s):  
Maria Pia Donzello ◽  
Giorgia De Mori ◽  
Elisa Viola ◽  
Claudio Ercolani ◽  
Giampaolo Ricciardi
Keyword(s):  
Photodynamic Therapy ◽  
Physicochemical Properties ◽  
Singlet Oxygen ◽  
Spectral Data ◽  
Free Base ◽  
Oxygen Generation ◽  
Singlet Oxygen Generation ◽  
Band Position ◽  
Uv Visible ◽  
Dimethylformamide Solution

The synthesis and physicochemical properties of the Zn II complexes, [ Py 8 QxPzZn ]( Py 8 QxPz = tetra -2,3-[6,7-di(2-pyridyl)quinoxalino]porphyrazinato dianion), the corresponding octacation [(2- Mepy )8 QxPzZn ]8+ (neutralized by I - ions), and the heteropentanuclear complex [( PdCl 2)4 Py 8 QxPzZn ] are presented and discussed. According to their UV-visible spectral data in non aqueous solvents ( CHCl 3, pyridine, dimethyl sulfoxide, dimethylformamide), the species exhibit intense absorptions in the Q-band region at 750–770 nm, in line with parallel spectral data observed for the free base [ Py 8 QxPzH 2], also reported, and the previously investigated Mg II complex [ Py 8 QxPzMg ( H 2 O )]. The observed Q-band position for this series of "quinoxalinoporphyrazine" macrocycles is about 100 nm to the red with respect to the position of the same absorption for the series of the already reported "pyrazinoporphyrazine" analogs. The spectral effects induced by the peripherally appended methyl-pyridinium groups in the octacation [(2- Mepy )8 QxPzZn ]8+ or by exocyclic coordination in the complex [( PdCl 2)4 Py 8 QxPzZn ] are also considered. Of the investigated Zn II complexes, [ Py 8 QxPzZn ] and the related octacation [(2- Mepy )8 QxPzZn ]8+ are active in dimethylformamide solution as singlet oxygen photosensitizers, which is of interest for applications in the photodynamic therapy (PDT) of cancer.

Germanium triazatetrabenzcorrole and germanium phthalocyanine: Synthesis, fluorescence and singlet oxygen generation

2018 ◽  
Vol 22 (09n10) ◽  
pp. 847-852 ◽  
Author(s):  
Xian-Fu Zhang ◽  
Xiaojie Sun
Keyword(s):  
Singlet Oxygen ◽  
Fluorescence Emission ◽  
Emission Spectra ◽  
Fluorescence Properties ◽  
Quantum Yields ◽  
Fluorescence Lifetimes ◽  
Fluorescence Emission Spectra ◽  
Oxygen Generation ◽  
Fluorescence Quantum Yields ◽  
Singlet Oxygen Generation

The synthesis, fluorescence properties and singlet oxygen generation capability of germanium tetrabenzotriazacorrole (LGeTBC), germanium phthalocyanine (Cl[Formula: see text]GePc) and their derivatives are described. Measurements include UV-vis absorption spectra, fluorescence emission spectra, fluorescence quantum yields fluorescence lifetimes, and singlet delta oxygen quantum yields. LGeTBC and its derivatives exhibit quite different spectral and fluorescence properties from their phthalocyanine precursor. Both LGeTBC and Cl[Formula: see text]GePc show high singlet delta oxygen quantum yields and suitable fluorescence quantum yields, indicating that they can act as good singlet oxygen photosensitizers for photodynamic therapy.

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