Spectroscopic, photophysical and photochemical properties of newly metallo-phthalocyanines containing coumarin derivative

Çapkin, Aylin; Pişkin, Mehmet; Durmuş, Mahmut; Bulut, Mustafa

doi:10.1016/j.molstruc.2020.128145

Cited by 23 publications

(13 citation statements)

References 32 publications

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“…The ΦF value of the MgPc 2 was lower than unsubstituted magnesium (II) phthalocyanine in DMF [27], which implies that the presence of the 2,6-dimethoxyphenoxy units reduced the fluorescence quenching of the Pc molecule. The ΦF value of the MgPc 2 is similar and typical of the other studied magnesium (II) Pc in DMF [37][38][39][40][41][42][43][44][45][46][47]. Fluorescence lifetime (τF) refers to the average time a molecule stays in its excited state before fluorescing, and its value is directly related to that of ΦF, i.e.…”

Section: Fluorescence Quantum Yield and Lifetimesupporting

confidence: 55%

Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine

Pişkin

Öztürk

Odabaş

2021

MANAS Journal of Engineering

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2(3),9(10),16(17),23(24)-tetrakis-2,6-dimethoxyphenoxy substituted magnesium (II) phthalocyanine, which has very good solubility in polar and non-polar solvents and does not aggregate, was synthesized. Its structure was characterized by spectroscopic methods such as elemental analysis, UV-vis, FT-IR, MALDI-TOF mass and 1 H NMR. It has very good solubility in polar aprotic solvents such as dimethyl sulfoxide, N, N-Dimethylformamide, tetrahydrofuran, dichloromethane, and non-polar solvents such as toluene, chloroform. Its aggregation properties have been studied both in the solvents mentioned above and in N, N-Dimethylformamide at different concentrations. Its photophysical properties were determined in N, N-dimethyl formamide. The effects of the nature and presence of 2,6-dimethoxyphenoxy group, which is an antioxidant derivative, on the phthalocyanine skeleton on the spectroscopic and photophysical properties were investigated by comparing it with unsubstituted magnesium (II) phthalocyanine. It can be a good nominee for various technological applications in that it does not aggregate and has good solubility in polar and non-polar solvents, as well as better and favorable fluorescence properties than its analog in the previous study.

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Section: Fluorescence Quantum Yield and Lifetimesupporting

confidence: 55%

Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine

Pişkin

Öztürk

Odabaş

2021

MANAS Journal of Engineering

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“…Due to these properties, the indium phthalocyanines ( 5 and 7 ) increase the transition between systems to populate triple state, thus reducing the number of fluorescent molecules and quenching them. [ 15 ] As seen in Table 1, it was observed that fluorescence excitation and emission maximum peaks of indium phthalocyanines were longer than the unsubstituted counterparts due to the coumarin substituents on phthalocyanine compounds, but Stokes shifts of these compounds were shorter than the unsubstituted counterparts due to the properties of central metal atom. Fluorescence emission, excitation maximum peaks, and Stokes shifts of zinc phthalocyanines ( 4 and 6 ) in DMF were given in Table 1.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3][4][5][6] A great number of properties of phthalocyanines arise from the π-electronic delocalization systems, which makes them valuable in different fields of science and technology such as optical recording, [7,8] photovoltaics, [9,10] sensor, [11,12] catalysis, [13] liquid crystals, [14] and photosensitizer in photodynamic therapy (PDT). [15][16][17][18][19][20] In recent years, PDT has been an important method of cancer treatment and includes three fundamental components: light, oxygen, and photosensitizer. [21,22] Phthalocyanines are suitable as a photosensitizer for PDT application because of the properties such as low dark toxicity, high singlet oxygen quantum yield, high molar absorption coefficient in the near-infrared wavelength, and long fluorescence lifetimes.…”

Section: Introductionmentioning

confidence: 99%

“…[ 1–6 ] A great number of properties of phthalocyanines arise from the π‐electronic delocalization systems, which makes them valuable in different fields of science and technology such as optical recording, [ 7,8 ] photovoltaics, [ 9,10 ] sensor, [ 11,12 ] catalysis, [ 13 ] liquid crystals, [ 14 ] and photosensitizer in photodynamic therapy (PDT). [ 15–20 ]…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization, and determination of photophysicochemical properties of peripheral and nonperipheral tetra‐7‐oxy‐3,4‐dimethylcoumarin substituted zinc, indium phthalocyanines

Artuç

Karapınar

Özdemir

et al. 2020

Applied Organom Chemis

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The photochemical and photophysical properties of peripheral and nonperipheral zinc and indium phthalocyanines containing 7-oxy-3,4-dimethylcoumarin synthesized were investigated in this study. 7-Hydroxy-3,4-dimethylcoumarin (1) was synthesized via Pechmann condensation reaction and then the phthalonitrile derivatives [4-(7-oxy-3,4-dimethylcoumarino)phthalonitrile (2) and 3-(7-oxy-3,-4-dimethylcoumarino)phthalonitrile (3)] were synthesized by nucleophilic aromatic substitution. Phthalocyanine compounds containing coumarin units on peripheral (4 and 5) and nonperipheral (6 and 7) positions were prepared via cyclotetramerization of phthalonitrile compounds. All compounds' characterizations were performed by spectroscopic methods and elemental analysis. The phthalocyanine derivatives' (4-7) photochemical and photophysical properties were studied in DMF. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen and photodegradation quantum yields) properties of these novel phthalocyanines (4-7) were studied in DMF. They produced good singlet oxygen (e.g., Φ Δ = 0.93 for 7) and showed appropriate photodegradation (in the order of 10 −5), which is very important for photodynamic therapy applications.

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“…Coumarin, also known as 1,2‐benzopyrone, is a large conjugated structure with strong modifiability formed by benzene and pyrone rings, which can introduce a variety of functional groups, [ 13 ] so it is widely used in biomedicine, functional materials, and optoelectronic materials. [ 14 ] In addition, coumarin compounds have a variety of biological activities such as anti‐inflammatory, [ 15,16 ] antiviral, [ 17 ] antibacterial, [ 18 ] antioxidant, [ 19 ] and antitumor activities [ 20–22 ] (Coumarin 1, Coumarin 2, Coumarin 3, Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antiproliferative activities, and DNA binding of coumarin‐3‐formamido derivatives

Shi

Chen

et al. 2020

Archiv der Pharmazie

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Ten coumarin‐3‐formamido derivatives, N‐benzyl‐coumarin‐3‐carboxamide (2), N‐fluorobenzyl‐coumarin‐3‐carboxamide (3–5), N‐methoxybenzyl‐coumarin‐3‐carboxamide (6–8), N‐((1‐methyl‐1H‐imidazol‐5‐yl)methyl)‐coumarin‐3‐carboxamide (9), N‐(thiophen‐2‐ylmethyl)‐coumarin‐3‐carboxamide (10), and N‐(furan‐2‐ylmethyl)‐coumarin‐3‐carboxamide (11), were synthesized and characterized. Compound 5 crystallizes in a monoclinic system P21/c space group with four chemical formulas in a unit cell; molecules of compound 5 are self‐assembled into a two‐dimensional supramolecular structure by intermolecular hydrogen bonds and C⋯C π stacking. The potential anticancer effects of these compounds on HeLa (cervical carcinoma), MCF‐7 (breast), A549 (lung), HepG2 (liver), and human umbilical vein (HUVEC) cells were examined. Compared with compounds 1–8 and 10–11, compound 9 exhibits potent in vitro cytotoxicity against HeLa cells and lower cytotoxicity against normal cells. Therefore, further in‐depth investigations of compound 9 were performed. Absorption titration experiments and fluorescence spectroscopy studies suggested that compound 9 binds to DNA through the intercalation mode.

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Spectroscopic, photophysical and photochemical properties of newly metallo-phthalocyanines containing coumarin derivative

Cited by 23 publications

References 32 publications

Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine

Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine

Synthesis, characterization, and determination of photophysicochemical properties of peripheral and nonperipheral tetra‐7‐oxy‐3,4‐dimethylcoumarin substituted zinc, indium phthalocyanines

Synthesis, antiproliferative activities, and DNA binding of coumarin‐3‐formamido derivatives

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