scholarly journals Simple Nonionic Omnisoluble Tetraphenylporphyrin for Relative Referencing of Singlet Oxygen Quantum Yield

2021 ◽  
Author(s):  
Daniel T. Payne ◽  
Jan Hynek ◽  
Jan Labuta ◽  
Jonathan P. Hill
Keyword(s):  
Quantum Yield ◽  
Singlet Oxygen ◽  
New Materials ◽  
Reference Compound

Meso-tetrakis-(3,4,5-tris{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}phenyl)porphyrin TEG12PH2 is reported as an ‘omnisoluble’ TPP reference for singlet oxygen (1O2) generation quantum yield (ΦSO) estimation. TEG12PH2 is a highly soluble, nonionic compound possessing excellent 1O2 QY in a wide variety of common solvents, including water. TEG12PH2 was prepared on multigram scale by the 12-way O-alkylation of tetrakis(3,4,5-trihydroxyphenyl)porphyrin using 2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-toluenesulfonate as reaction solvent. The corresponding Zn(II) complex TEG12PZn was also prepared and studied. Its 1O2 QYs in the different solvents studied were found to be 0.86 (acetone), 0.59 (acetonitrile), 0.66 (chloroform), 0.85 (methanol), 0.45 (toluene) and 0.51 (water). TEG12PH2 can be considered a reliable and easy to implement omnisoluble reference compound for the estimation of the 1O2 generating activities of new materials, especially new porphyrinic compounds.

scholarly journals Ruthenium-based PACT agents based on bisquinoline chelates: synthesis, photochemistry, and cytotoxicity

2021 ◽  
Author(s):  
Anja Busemann ◽  
Ingrid Flaspohler ◽  
Xue-Quan Zhou ◽  
Claudia Schmidt ◽  
Sina K. Goetzfried ◽  
...  
Keyword(s):  
Quantum Yield ◽  
Singlet Oxygen ◽  
Cancer Cells ◽  
Cellular Uptake ◽  
Ruthenium Complex ◽  
Human Cancer ◽  
Light Irradiation ◽  
Quantum Yields ◽  
Light Activation ◽  
Human Cancer Cells

AbstractThe known ruthenium complex [Ru(tpy)(bpy)(Hmte)](PF6)2 ([1](PF6)2, where tpy = 2,2’:6’,2″-terpyridine, bpy = 2,2’-bipyridine, Hmte = 2-(methylthio)ethanol) is photosubstitutionally active but non-toxic to cancer cells even upon light irradiation. In this work, the two analogs complexes [Ru(tpy)(NN)(Hmte)](PF6)2, where NN = 3,3'-biisoquinoline (i-biq, [2](PF6)2) and di(isoquinolin-3-yl)amine (i-Hdiqa, [3](PF6)2), were synthesized and their photochemistry and phototoxicity evaluated to assess their suitability as photoactivated chemotherapy (PACT) agents. The increase of the aromatic surface of [2](PF6)2 and [3](PF6)2, compared to [1](PF6)2, leads to higher lipophilicity and higher cellular uptake for the former complexes. Such improved uptake is directly correlated to the cytotoxicity of these compounds in the dark: while [2](PF6)2 and [3](PF6)2 showed low EC50 values in human cancer cells, [1](PF6)2 is not cytotoxic due to poor cellular uptake. While stable in the dark, all complexes substituted the protecting thioether ligand upon light irradiation (520 nm), with the highest photosubstitution quantum yield found for [3](PF6)2 (Φ[3] = 0.070). Compounds [2](PF6)2 and [3](PF6)2 were found both more cytotoxic after light activation than in the dark, with a photo index of 4. Considering the very low singlet oxygen quantum yields of these compounds, and the lack of cytotoxicity of the photoreleased Hmte thioether ligand, it can be concluded that the toxicity observed after light activation is due to the photoreleased aqua complexes [Ru(tpy)(NN)(OH2)]2+, and thus that [2](PF6)2 and [3](PF6)2 are promising PACT candidates. Graphic abstract

scholarly journals Synthesis and Physicochemical Properties of [(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-thiophen-5-yl-substituted Tetrapyrazinoporphyrazine with Magnesium(II) Ion

2021 ◽  
Vol 11 (6) ◽  
pp. 2576
Author(s):  
Sebastian Lijewski ◽  
Jiří Tydlitát ◽  
Beata Czarczynska-Goslinska ◽  
Milan Klikar ◽  
Jadwiga Mielcarek ◽  
...  
Keyword(s):  
Quantum Yield ◽  
Singlet Oxygen ◽  
2D Nmr ◽  
Nmr Studies ◽  
Oxygen Formation ◽  
Nmr Techniques ◽  
Flash Column Chromatography ◽  
Photochemical Stability ◽  
Singlet Oxygen Formation ◽  
Very High

Tetrapyrazinoporphyrazine with peripheral menthol-thiophenyl substituents was synthesized using Linstead conditions and purified by flash column chromatography. The optimized synthetic and purification procedures allowed us to obtain a new macrocycle with 36% yield. Tetrapyrazinoporphyrazine derivative was characterized by UV–Vis and NMR spectroscopy, as well as MS spectrometry. Complex NMR studies using 1D and 2D NMR techniques allowed the analysis of the bulky menthol-thiophenyl substituted periphery of the new macrocycle. Further, photochemical stability and singlet oxygen quantum yield were determined by indirect method with diphenylisobenzofuran. The new tetrapyrazinoporphyrazine revealed low generation of singlet oxygen with a quantum yield of singlet oxygen formation at 2.3% in dimethylformamide. In turn, the macrocycle under irradiation with visible light presented very high stability with quantum yield for photostability of 9.59 × 10−6 in dimethylformamide, which figures significantly exceed the border for its classification as a stable porphyrinoid (10−4–10−5).

Linear and high-molecular-weight poly-porphyrins for efficient photodynamic therapy

2021 ◽  
Author(s):  
Nan Zheng ◽  
Xiahui Li ◽  
Shangwei Huangfu ◽  
Kangkai Xia ◽  
Ruofei Yue ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Photodynamic Therapy ◽  
Quantum Yield ◽  
Singlet Oxygen ◽  
High Molecular Weight ◽  
Linear Poly ◽  
High Molecular Weight Poly

A linear poly-porphyrin with high Mw and conjugated by PEG and acetazolamide was developed with enhanced singlet oxygen quantum yield, improved photo-toxicity and excellent in vivo photodynamic therapy.

New soluble 4-(4-formyl-2,6-dimethoxyphenoxy) substituted phthalocyanines: Synthesis, characterization, photophysical and photochemical properties

2021 ◽  
pp. 1-10
Author(s):  
Ibrahim Erden ◽  
Betül Karadoğan ◽  
Fatma Aytan Kılıçarslan ◽  
Göknur Yaşa Atmaca ◽  
Ali Erdoğmuş
Keyword(s):  
Quantum Yield ◽  
Singlet Oxygen ◽  
Fluorescence Quantum Yield ◽  
Metal Ion ◽  
Mass Spectra ◽  
Quantum Yields ◽  
Therapeutic Outcomes ◽  
Ft Ir ◽  
Photochemical Properties ◽  
New Compounds

This work describes the synthesis, spectral and fluorescence properties of bis 4-(4-formyl-2,6-dimethoxyphenoxy) substituted zinc (ZnPc) and magnesium (MgPc) phthalocyanines. The new compounds have been characterized by elemental analysis, UV-Vis, FT-IR, 1H-NMR and mass spectra. Afterward, the effects of including metal ion on the photophysicochemical properties of the complexes were studied in biocompatible solvent DMSO to analyze their potential to use as a photosensitizer in photodynamic therapy (PDT). The fluorescence and singlet oxygen quantum yields were calculated as 0.04–0.15 and 0.70–0.52 for ZnPc and MgPc, respectively. According to the results, MgPc has higher fluorescence quantum yield than ZnPc, while ZnPc has higher singlet oxygen quantum yield than MgPc. The results show that the synthesized complexes can have therapeutic outcomes for cancer treatment.

Determination of the quantum yield of singlet oxygen sensitized by halogenated boron difluoride dipyrromethenes

2017 ◽  
Vol 51 (3) ◽  
pp. 175-181 ◽  
Author(s):  
R. T. Kuznetsova ◽  
Iu. V. Aksenova ◽  
D. E. Bashkirtsev ◽  
A. S. Shulev ◽  
E. V. Antina ◽  
...  
Keyword(s):  
Quantum Yield ◽  
Singlet Oxygen ◽  
Boron Difluoride

IMPROVEMENT OF THE PHOTOPHYSICAL PARAMETERS OF ZINC OCTACARBOXY PHTHALOCYANINE UPON CONJUGATION TO MAGNETIC NANOPARTICLES

2013 ◽  
Vol 12 (02) ◽  
pp. 1350010 ◽  
Author(s):  
PHILLIMON MODISHA ◽  
EDITH ANTUNES ◽  
JOHN MACK ◽  
TEBELLO NYOKONG
Keyword(s):  
Magnetic Nanoparticles ◽  
Quantum Yield ◽  
Singlet Oxygen ◽  
Amide Bond ◽  
Amino Group ◽  
Covalent Linkage ◽  
Transmission Electron ◽  
Photophysical Parameters ◽  
Photophysical Behavior ◽  
Triplet Lifetime

Magnetic nanoparticles (MNPs) comprising magnetite (Fe3O4) were functionalized with 3-aminopropyl-triethoxysilane forming amino functionalized magnetite nanoparticles (AMNPs). The amino group allows for conjugation with zinc octacarboxyphthalocyanine ( ZnOCPc ) via the carboxyl group to form an amide bond. Transmission electron microscopy showed a change in morphology after conjugation. The covalent linkage of AMNPs to ZnOCPc has shown improvements in the photophysical behavior of the Pc in the presence of the MNP, increasing the triplet quantum yield (ΦT), singlet oxygen quantum yield (ΦΔ), triplet lifetime (τT) and singlet oxygen lifetime (τΔ) of the ZnOCPc and thus improving the efficiency of the ZnOCPc as a photosensitizer.

scholarly journals Спектральное исследование фотодинамических процессов в системе C-=SUB=-60-=/SUB=--(н-метилпирролидон)-кислород

2021 ◽  
Vol 129 (12) ◽  
pp. 1493
Author(s):  
И.М. Кисляков ◽  
И.М. Белоусова ◽  
В.М. Киселев ◽  
И.В. Багров ◽  
А.М. Стародубцев ◽  
...  
Keyword(s):  
Quantum Yield ◽  
Singlet Oxygen ◽  
Transient Absorption ◽  
Rapid Quenching ◽  
Quenching Rate ◽  
Broadband Absorption ◽  
Laser Pumping ◽  
Time Dependencies ◽  
Quenching Rate Constant

The processes of photoexcitation and energy transfer in an air-saturated solution of fullerene C60 in n-methylpyrrolidone are studied. With femtosecond laser pumping at a wavelength л(p) = 520 nm, transient absorption spectra were obtained in the range 470-750 nm. Broadband absorption is observed at л > 650 nm as a result of aggregation of fullerene molecules, characterized by a short decay time of the picosecond scale. The analysis of the time dependencies indicates the presence of several processes. Within the proposed interpretation, we state a remarkable reduction in the time of singlet-triplet intersystem crossing with an increase of nanocluster size while the rapid quenching of the singlet state varies only slightly. The quantum yield of the triplet state can therefore increase, reaching 0.14. The phosphorescence spectra of singlet oxygen with a maximum at л = 1276 nm were measured with LED excitation at various wavelengths in the range 370-625 nm. The lifetime and quenching rate constant of singlet oxygen in n-methylpyrrolidone are determined. The combined quantum yield of triplet fullerene and singlet oxygen in n-methylpyrrolidone is estimated as 0.74. The efficiency spectra of the singlet oxygen photosensibilization in the C60-(n-methylpyrrolidone)-oxygen system are obtained, indicating the increasing role of large nanoclusters in this process during aging of the solution.

scholarly journals Heavy atom-free semiconducting polymer with high singlet oxygen quantum yield for prostate cancer synergistic phototherapy

2019 ◽  
Vol 3 (6) ◽  
pp. 1123-1127 ◽  
Author(s):  
Jian Shen ◽  
Jianjiao Chen ◽  
Zhen Ke ◽  
Dengfeng Zou ◽  
Liguo Sun ◽  
...  
Keyword(s):  
Prostate Cancer ◽  
Cancer Therapy ◽  
Quantum Yield ◽  
Singlet Oxygen ◽  
Heavy Atom ◽  
Semiconducting Polymer ◽  
Prostate Cancer Therapy

Heavy atom free NDNT have a great potential for prostate cancer therapy both in vitro and in vivo.

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