Synthesis, electrochemistry and in situ spectroelectrochemistry of novel hexadeca-substituted phthalocyanines with three different groups

Kurt, Özge; Koca, Atıf; Gül, Ahmet; Koçak, Makbule Burkut

doi:10.1016/j.synthmet.2015.05.012

Cited by 29 publications

(26 citation statements)

References 60 publications

(92 reference statements)

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“…Generally, modification of the Pc ring diminishes π‐stacking interactions between the planar macromolecules. The presence of alkyl, alkoxy, alkylthio, phenoxy or ester groups on the periphery of the Pc ring improves the solubility of Pcs in common organic solvents (6,9), whereas the substitution of sulfonyl (10), amino (11) or carboxyl substituents (12) makes them soluble in water. Besides, nature, size and location of the substituents affect the electronic and spectroscopic properties of the substituted Pcs.…”

Section: Introductionmentioning

confidence: 99%

“…There are mostly two functional alternatives to overcome these problems. First, insertion of different metal ions into the Pc core (1)(2)(3)(4)(5)(6), and second, alteration of the Pc ring by addition of long and bulky substituents at peripheral (positions of the benzene ring, at 2,3,9,10,16,17,23,24) and/or nonperipheral (at 1,4,8,11,15,18,22,25) positions (1)(2)(3)7,8). Generally, modification of the Pc ring diminishes p-stacking interactions between the planar macromolecules.…”

Section: Introductionmentioning

confidence: 99%

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Effect of Position and Connected Atom on Photophysical and Photochemical Properties of Some Fluorinated Metallophthalocyanines

Sağlam

Farajzadeh

Atmaca

et al. 2020

Photochem & Photobiology

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This study presents the preparation of a new phthalonitrile derivative namely 3‐(4‐(trifluoromethoxy)thiophenoxy)phthalonitrile (1) and a series of its metallated phthalocyanines (M = Zn (II) (1a) and In(III) (1b)). In addition, the peripheral analog of the indium phthalocyanine chloride (2b) was newly synthesized. Characterization of the resulting compounds was carried out by utilizing various spectroscopic methods such as FT‐IR, 1H NMR and UV‐Vis spectroscopy. The influence of concentration on aggregation properties of compound 1a was investigated at different concentrations of DMSO. The effect of solvent type on aggregation properties of compound 1a was studied, as well. According to the referred procedures, the macrocyclic molecules (2a, 3a‐b and 4a‐b) were prepared. The effect of some parameters including metal ion, the position of the substituent and the connected atom (oxo or thio) on photochemical and photophysical features of compounds (1a‐b, 2a‐b, 3a‐b, and 4a‐b) was studied for evaluation of their potential as a photosensitizer in PDT, comparatively. The highest singlet oxygen quantum yields (ΦΔ = 0.71 for 1a and 0.80 for 2b) were obtained for complexes 1a and 1b in DMSO. The photophysical and photochemical features of the studied macromolecules are therefore suitable for photodynamic therapy applications.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Effect of Position and Connected Atom on Photophysical and Photochemical Properties of Some Fluorinated Metallophthalocyanines

Sağlam

Farajzadeh

Atmaca

et al. 2020

Photochem & Photobiology

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“…By recognition of these specific properties, much attention has been paid to study the advantage of their use in many high‐tech fields, but high intermolecular interactions of Pc rings lead to less solubility and high aggregation of Pcs, which can be improved by alteration of their medium. [ 1–3 ] There are mainly two ways: (1) the insertion of various metal ions in the Pc core [ 4–6 ] and (2) the addition of long and bulky substituents at peripheral and/or nonperipheral positions. [ 7,8 ] Besides, the presence of the ligand on the metal ion can decrease the π stacking interactions and increase their solubility.…”

Section: Introductionmentioning

confidence: 99%

Investigation of tyrosinase enzyme (from mushroom) inhibitory activities and antioxidant properties of new fluorine‐containing phthalocyanines

Farajzadeh

Sağlam

Akın

et al. 2020

Archiv der Pharmazie

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A series of new peripherally or nonperipherally substituted phthalocyanines bearing 4‐(trifluoromethoxy)thiophenyl groups was synthesized. In addition, a new metal‐free phthalocyanine bearing 4‐(trifluoromethoxy)phenoxy on the nonperipheral position was prepared. The resulting phthalocyanines were characterized using some spectroscopic techniques such as 1H nuclear magnetic resonance, Fourier‐transform infrared spectroscopy, and UV–Vis spectroscopy, together with elemental analysis. When the tyrosinase enzyme inhibition activities of the synthesized phthalocyanines were examined, molecules 2b and 3b showed an inhibitory activity against the enzyme with IC50 values of 176.2 ± 0.65 and 284.4 ± 1.03, respectively. The inhibition types of the molecules and standard inhibitor kojic acid were found as competitive for 2b, mixed for 1b and kojic acid, and uncompetitive for 3b. Antioxidant activities were also assessed by using 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) and reducing power assays, and the molecules showed moderate antioxidant activities.

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“…The insertion of the substituents at both peripheral (β-positions) and non-peripheral (α-) positions of the Pcs results in the formation of hexadeca-substituted Pcs that are comparatively less studied than the corresponding octa-and tetra-substituted derivatives. Studies about Pcs with different substituents at αand β-positions have also been published [13][14][15][16][17]. Most of these studies involved the synthesis and characterization of novel hexadeca-substituted Pcs.…”

Section: Introductionmentioning

confidence: 99%

α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties

Karaoğlu

Burat

2020

Molecules

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Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H2Pc) were prepared. FT-IR, mass, electronic absorption, 1H NMR, and 13C NMR spectroscopy were employed for the characterization of all compounds. The effect of hexadeca substituents on the photophysical properties of metal-free Pcs was investigated. Photophysical properties of H2Pc were studied in tetrahydrofuran (THF). Fluorescent quantum yields of phthalocyanines (Pcs) were calculated and compared with the unsubstituted phthalocyanine. 1,4-Benzoquinone effectively quenched the fluorescence of these compounds in THF. Cyclic and square wave voltammetry methods were applied to metal-free phthalocyanines and Pc-centered oxidation and reduction processes were obtained.

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Synthesis, electrochemistry and in situ spectroelectrochemistry of novel hexadeca-substituted phthalocyanines with three different groups

Cited by 29 publications

References 60 publications

Effect of Position and Connected Atom on Photophysical and Photochemical Properties of Some Fluorinated Metallophthalocyanines

Effect of Position and Connected Atom on Photophysical and Photochemical Properties of Some Fluorinated Metallophthalocyanines

Investigation of tyrosinase enzyme (from mushroom) inhibitory activities and antioxidant properties of new fluorine‐containing phthalocyanines

α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties

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