Investigation of photophysical and photochemical properties of phthalocyanines bearing fluorinated groups

Korkmaz, Eda; Ahmetali, Erem; Atmaca, Göknur Yaşa; Karaoğlu, Hande Pekbelgin; Erdoğmuş, Alı; Koçak, Makbule Burkut

doi:10.1007/s00706-019-02543-y

Cited by 21 publications

(13 citation statements)

References 31 publications

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“…Since compound 1a obeys the Lambert–Beer law, aggregation does not rely on concentration at the studied range of concentration (Fig. 5) (29–34,41,42).…”

Section: Resultsmentioning

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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“…Since compound 1a obeys the Lambert–Beer law, aggregation does not rely on concentration at the studied range of concentration (Fig. 5) (29–34,41,42).…”

Section: Resultsmentioning

confidence: 99%

“…Spectral properties of Pcs as a function of the electronic states change by enhancement of p-stacking which derange of the electronic states. Furthermore, the study of the electronic absorption spectra of Pcs is a useful approach for measurement and management of their aggregation (1)(2)(3)(4)(29)(30)(31)(32)(33)(34)41,42).…”

Section: Aggregation Studiesmentioning

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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“…Synthesis of the following phthalocyanine 56 in Scheme 11 begins with preparing the fluorinated phthalonitrile under basic conditions through a nucleophilic aromatic substitution reaction using 4-nitrophthalonitrile and 3,5-bis(trifluoromethyl)phenol mixture in DMF [ 52 ]. In step 2, a cyclotetramerization reaction occurred using dimethylethanolamine (DMAE) and zinc chloride to synthesize phthalocyanine 56 at a low yield of 11%.…”

Section: Fluorinated Phthalocyanine Dyesmentioning

confidence: 99%

Synthesis and Applications of Selected Fluorine-Containing Fluorophores

Casa

Henary

2021

Molecules

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The synthesis of fluorine-containing small molecules has had numerous benefits of improving the quality and efficiency of many applications of these compounds. For example, fluorine adds promising functionalities in various areas of imaging (MRI, PET, and NIR); gives cell-targeting properties; and has demonstrated improvements in cell permeability, solubility, and other pharmacologic properties. For these and other numerous reasons, fluorination of molecules has grown in popularity in various fields of chemistry. Many reports show the effects observed from increasing the number of fluorine atoms on a fluorophore scaffold. This report will cover the most significant applications and improvements that fluorine has contributed to in various dye scaffolds such as BODIPY, rhodamine, phthalocyanine, and cyanine in the recent decade.

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“…Spectral properties of Pcs as a function of the electronic states change by enhancement of π-stacking which derange of the electronic states. Furthermore, the study of the electronic absorption spectra of Pcs is a useful approach for the measurement and management of the aggregation [24,25]. The concentrationeffect on aggregation properties of compounds 4, 5, and 6 was examined in different molarity of THF, DMSO, and DMF,ranging from 2 × 10 -6 to 12 × 10 -5 M. As concentration increased, the absorbance enhanced directly in a constant value, and no new band was observed.…”

Section: Syntheses and Characterizationmentioning

confidence: 99%

Newly synthesized peripherally octa-substituted zinc phthalocyanines carrying halogen terminated phenoxy-phenoxy moiety: comparative photochemical and photophysical features

Kırbaç

Erdoğmuş

2020

Turk J Chem

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This study reports the 3 new phthalonitrile derivatives, namely 4, 5 Bis-[4-(4-bromophenoxy) phenoxy] phthalonitrile ( 1 ), 4,5 Bis-[4-(4-chlorophenoxy) phenoxy]phthalonitrile ( 2 ), and 4, 5 Bis[4-(4-fluorophenoxy) phenoxy] phthalonitrile ( 3 ). Their octa-substituted zinc phthalocyanines ( 4 , 5 , 6 ) are reported for the first time in this study. The resulting compounds were characterized by utilizing some spectroscopic methods, such as UV-Vis, 1HNMR, FT-IR spectroscopy, as well as mass spectraand elemental analysis. To show photosynthesizer’s potential, emission (F F ), singlet oxygen (1O2), and photodegradation quantum yields (F∆, Fd) of octa-peripherally phthalocyanines (Pcs) were performed in the solutions, such as biocompatible solvent DMSO (dimethyl sulfoxide) as well as DMF (dimethylformamide) and THF (tetrahydrofuran). Solvent and octa-peripherally binding effect of the halogen (Br, Cl, F) terminated phenoxy-phenoxy groups on phthalocyanine rings for photophysicochemical properties ( 4 , 5 , and 6 ) were compared with the tetra-peripherally and tetra nonperipherally substituted derivatives. The new dyes ( 4 to 6 ) may be evaluated in photodynamic therapy (PDT) of cancer as photosensitizers due to efficient 1O2 from 0.55 to 0.75.

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Investigation of photophysical and photochemical properties of phthalocyanines bearing fluorinated groups

Cited by 21 publications

References 31 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

Synthesis and Applications of Selected Fluorine-Containing Fluorophores

Newly synthesized peripherally octa-substituted zinc phthalocyanines carrying halogen terminated phenoxy-phenoxy moiety: comparative photochemical and photophysical features

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