Spectroscopic and quantum chemical study of phthalocyanines with 1,4,7-trioxanonyl moieties

Wierzchowski, Marcin; Sobotta, Łukasz; Łażewski, Dawid; Kasprzycki, Piotr; Fita, Piotr; Gośliński, Tomasz

doi:10.1016/j.molstruc.2019.127371

Cited by 11 publications

(6 citation statements)

References 33 publications

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“…The 6-31+G(d,p) basis function was chosen in the DT-DFT simulations because of its relatively low computational cost. This function was successfully applied in the metal–ligand (metal–dye) TD-DFT simulations [ 49 ] and phthalocyanine–metal complexes [ 50 ]. A hybrid functional exchange-correlation PBE1PBE was chosen, which gave accurate results in the TD-DFT simulation of the metal–ligand complexes [ 51 , 52 ], including phthalocyanines [ 53 ].…”

Section: Resultsmentioning

confidence: 99%

Novel Short PEG Chain-Substituted Porphyrins: Synthesis, Photochemistry, and In Vitro Photodynamic Activity against Cancer Cells

Łażewski

Kucińska

Potapskiy

et al. 2022

IJMS

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This work presents the synthesis and characterization of metal-free, zinc (II), and cobalt (II) porphyrins substituted with short PEG chains. The synthesized compounds were characterized by UV-Vis, 1H and 13C NMR spectroscopy, and MALDI-TOF mass spectrometry. The origin of the absorption bands for tested compounds in the UV-Vis range was determined using a computational model based on the electron density functional theory (DFT) and its time-dependent variant (TD-DFT). The photosensitizing activity was evaluated by measuring the ability to generate singlet oxygen (ΦΔ), which reached values up to 0.54. The photodynamic activity was tested using bladder (5637), prostate (LNCaP), and melanoma (A375) cancer cell lines. In vitro experiments clearly showed the structure–activity relationship regarding types of substituents, their positions in the phenyl ring, and the variety of central metal ions on the porphyrin core. Notably, the metal-free derivative 3 and its zinc derivative 6 exerted strong cytotoxic activity toward 5637 cells, with IC50 values of 8 and 15 nM, respectively. None of the tested compounds induced a cytotoxic effect without irradiation. In conclusion, these results highlight the potential value of the tested compounds for PDT application.

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Section: Resultsmentioning

confidence: 99%

Novel Short PEG Chain-Substituted Porphyrins: Synthesis, Photochemistry, and In Vitro Photodynamic Activity against Cancer Cells

Łażewski

Kucińska

Potapskiy

et al. 2022

IJMS

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“…Due to its paramagnetic nature, Another spectral device related to the structure of phthalocyanines is UV spectroscopy. It gives absorbance value for Q and B bands which are characteristic for phthalocyanines [17]. It also indicates that the phthalocyanine compound does not bind the metal bond [18].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, DFT Calculations, Photophysical, Photochemical Properties of Peripherally Metallophthalocyanines Bearing (2-(Benzo[d] [1,3] Dioxol-5-Ylmethoxy) Phenoxy) Substituents

Solğun

Yıldıko

Ağırtaş

2021

Polycyclic Aromatic Compounds

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4- (2-(benzo[d] [1, 3] dioxol-5-ylmethoxy) phenoxy) phthalonitrile was rst prepared as a starting material.Then, this new phthalonitrile derivative was reacted with Zn and Co salts to obtain new phthalocyanine complexes. Phthalocyanine complexes were evaluated by uorescence emission, extinction, and absorption measurements. Aggregation studies show the compliance with the lambert-beer law in the concentration range studied for peripheral phthalocyanine compounds. The density functional theory (DFT) calculations of the metallophthalocyanines compounds were performed using B3LYP / 6-31G in Zn-Pc and B3LYP / LanL2DZ in Co-Pc to derive structural optimization, HOMO-LUMO energy parameters, and NLO properties. The calculated values of M-Pcs with different center atoms were obtained close to each other. Molecular electronic surface (MEP) maps of the studied compounds are mapped and discussed. The HOMO-LUMO energy gaps of our compounds studied are around 2.1 eV. The docking studies were performed with the phthalonitrile.

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“…Another spectral device related to the structure of phthalocyanines is UV spectroscopy. It gives absorbance value for Q and B bands which are characteristic for phthalocyanines [17]. It also indicates that the phthalocyanine compound does not bind the metal bond [18].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, DFT calculations, photophysical, photochemical properties of peripherally metallophthalocyanines bearing (2-(benzo[d] [1,3] dioxol-5-ylmethoxy) phenoxy) substituents

Solğun

Yıldıko

Ağırtaş

2021

Preprint

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4-(2-(benzo[d] [1, 3] dioxol-5-ylmethoxy) phenoxy) phthalonitrile was first prepared as a starting material. Then, this new phthalonitrile derivative was reacted with Zn and Co salts to obtain new phthalocyanine complexes. Phthalocyanine complexes were evaluated by fluorescence emission, extinction, and absorption measurements. Aggregation studies show the compliance with the lambert-beer law in the concentration range studied for peripheral phthalocyanine compounds. The density functional theory (DFT) calculations of the metallophthalocyanines compounds were performed using B3LYP / 6-31G in Zn-Pc and B3LYP / LanL2DZ in Co-Pc to derive structural optimization, HOMO-LUMO energy parameters, and NLO properties. The calculated values of M-Pcs with different center atoms were obtained close to each other. Molecular electronic surface (MEP) maps of the studied compounds are mapped and discussed. The HOMO-LUMO energy gaps of our compounds studied are around 2.1 eV. The docking studies were performed with the phthalonitrile.

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Spectroscopic and quantum chemical study of phthalocyanines with 1,4,7-trioxanonyl moieties

Cited by 11 publications

References 33 publications

Novel Short PEG Chain-Substituted Porphyrins: Synthesis, Photochemistry, and In Vitro Photodynamic Activity against Cancer Cells

Novel Short PEG Chain-Substituted Porphyrins: Synthesis, Photochemistry, and In Vitro Photodynamic Activity against Cancer Cells

Synthesis, DFT Calculations, Photophysical, Photochemical Properties of Peripherally Metallophthalocyanines Bearing (2-(Benzo[d] [1,3] Dioxol-5-Ylmethoxy) Phenoxy) Substituents

Synthesis, DFT calculations, photophysical, photochemical properties of peripherally metallophthalocyanines bearing (2-(benzo[d] [1,3] dioxol-5-ylmethoxy) phenoxy) substituents

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