Synthesis, characterisation and aggregation properties of novel metal-free and metallophthalocyanines containing four 21-membered oxatetrathiadiaza macrocycles

Gök, Yaşar; Farsak, Berna

doi:10.1016/j.jorganchem.2013.03.019

Cited by 9 publications

(6 citation statements)

References 37 publications

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“…The electronic absorption spectra of AlPcCl formulated in P‐123 micelles were similar to the spectrum in ethanol (monomeric AlPcCl) showing a small bathochromic shift of the main bands due to the change in medium polarity . On the other hand, AlPcCl incorporated in F‐127 showed significant changes in the spectral profile, thus indicating the presence of self‐aggregates .…”

Section: Resultsmentioning

confidence: 68%

Formulation of Aluminum Chloride Phthalocyanine in Pluronic^™ P‐123 and F‐127 Block Copolymer Micelles: Photophysical properties and Photodynamic Inactivation of Microorganisms

Vilsinski

Gerola

Enumo

et al. 2015

Photochem & Photobiology

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Aluminum Chloride Phthalocyanine (AlPcCl) can be used as a photosensitizer (PS) for Photodynamic Inactivation of Microorganisms (PDI). The AlPcCl showed favorable characteristics for PDI due to high quantum yield of singlet oxygen (ΦΔ ) and photostability. Physicochemical properties and photodynamic inactivation of AlPcCl incorporated in polymeric micelles of tri-block copolymer (P-123 and F-127) against microorganisms Staphylococcus aureus, Escherichia coli and Candida albicans were investigated in this work. Previously, it was observed that the AlPcCl undergoes self-aggregation in F-127, while in P-123 the PS is in a monomeric form suitable for PDI. Due to the self-aggregation of AlPcCl in F-127, this formulation did not show any effect on these microorganisms. On the other hand, AlPcCl formulated in P-123 was effective against S. aureus and C. albicans and the death of microorganisms was dependent on the PS concentration and illumination time. Additionally, it was found that the values of PS concentration and illumination time to eradicate 90% of the initial population of microorganisms (IC90 and D90 , respectively) were small for the AlPcCl in P-123, showing the effectiveness of this formulation for PDI.

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Section: Resultsmentioning

confidence: 68%

Formulation of Aluminum Chloride Phthalocyanine in Pluronic^™ P‐123 and F‐127 Block Copolymer Micelles: Photophysical properties and Photodynamic Inactivation of Microorganisms

Vilsinski

Gerola

Enumo

et al. 2015

Photochem & Photobiology

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“…21 All reagents and solvents were reagent grade quality and were obtained from commercial suppliers.…”

Section: Methodsmentioning

confidence: 99%

“…The starting phthalonitrile containing N-chloroacetamide 1 was prepared by following the route described in the literature. 21 All reagents and solvents were reagent grade quality and were obtained from commercial suppliers.…”

Section: Methodsmentioning

confidence: 99%

“…N,N'-(2,2'-(4,5-dicyano-1,2-phenylene)bis(sulfanediyl)bis(2,1-phenylene))bis(2-chloroacetamide) 1 was synthesized by following the procedure reported in the literature. 21 Generally, the synthesis of a macrocycle requires high dilution techniques or the template effect. The macrocyclization reaction was performed by adding a solution of 1 in dry dimethylformamide to a stirring solution of dithiol in dry dimethylformamide containing anhydrous sodium carbonate as the base at 0-5 • C. Final purification by silica gel chromatography afforded the macrocycle 6,16-dioxo-5,6,7,9,10,12,13,15,16,17decahydrotribenzo[k, n, q] [1,4,7,13,16,10,19]pentathiadiazacyclohenicosine-24,25-dicarbonitrile 2 in 49% yield.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

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Novel metal-free and metallophthalocyanines containing four 21-membered pentathiadiaza macrocycles: synthesis, characterization, and study of aggregation properties

Gök¹,

Farsak²,

Keleş³

et al. 2014

Turk J Chem

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Metal-free phthalocyanine 3 and its metallophthalocyanine derivatives 4, 5, and 6 (M = Zn, Co, and Ni) substituted with four 21-membered pentathiadiaza macrocycles were synthesized and their structures identified by elemental analysis, IR, 1 H NMR, mass, and UV-Vis spectroscopy techniques. The aggregation properties of phthalocyanines 4, 5, and 6 were investigated in different solvents and at different concentrations of dimethylformamide.

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“…A series of structurally similar phthalocyanines 5b-5d and 6b-6d bearing 21-membered macrocycles peripherally with different types of donor atoms reported before by our group showed similar results for the Q band positions (Scheme 2). 53,54 When comparing the phthalocyanines 5b-5d and 6b-6d with the phthalocyanines 3b-3d, phthalocyanine derivatives 5b-5d and 6b-6d contain one more oxygen and sulfur donor atoms, respectively, instead of one carbon atom in the phthalocyanines 3b-3d. In the case of phthalocyanine derivatives 2b-2d, 3b-3d, and 4b-4d, which are substituted by four 18-, 19-, and 21-membered macrocycles with N 2 S 4 donor atoms, respectively (Scheme 3), they all have the same phthalocyanine skeleton substituted different ring-sized macrocycles at peripheral positions.…”

Section: Absorption Propertiesmentioning

confidence: 99%

Synthesis of metal-free and metallophthalocyanines containing 18- and 21-membered macrocycles with mixed donor atoms and their metal-ion binding properties

Gök¹

2015

Turk J Chem

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This paper describes the synthesis of a series of metal-free phthalocyanines and metallophthalocyanines peripherally substituted by macrocycles of different ring sizes with the same donor atom sets. The effects of varying ring size of the macrocycle on the spectroscopic and metal ion binding properties of phthalocyanines were examined. For these purposes, electronic absorption properties for metal-free phthalocyanines and metallophthalocyanines were studied in dimethylformamide and tetrahydrofuran. The liquid-liquid extraction of metal picrates such as Ag(I), Hg(II), Cd(II), Zn(II), Cu(II), Ni(II), Pb(II), and Co(II) from the aqueous phase to the organic phase was carried out using metallophthalocyanines. All new compounds were characterized using several spectroscopic techniques.

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Synthesis, characterisation and aggregation properties of novel metal-free and metallophthalocyanines containing four 21-membered oxatetrathiadiaza macrocycles

Cited by 9 publications

References 37 publications

Formulation of Aluminum Chloride Phthalocyanine in Pluronic^™ P‐123 and F‐127 Block Copolymer Micelles: Photophysical properties and Photodynamic Inactivation of Microorganisms

Formulation of Aluminum Chloride Phthalocyanine in Pluronic^™ P‐123 and F‐127 Block Copolymer Micelles: Photophysical properties and Photodynamic Inactivation of Microorganisms

Novel metal-free and metallophthalocyanines containing four 21-membered pentathiadiaza macrocycles: synthesis, characterization, and study of aggregation properties

Synthesis of metal-free and metallophthalocyanines containing 18- and 21-membered macrocycles with mixed donor atoms and their metal-ion binding properties

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Synthesis, characterisation and aggregation properties of novel metal-free and metallophthalocyanines containing four 21-membered oxatetrathiadiaza macrocycles

Cited by 9 publications

References 37 publications

Formulation of Aluminum Chloride Phthalocyanine in Pluronic™ P‐123 and F‐127 Block Copolymer Micelles: Photophysical properties and Photodynamic Inactivation of Microorganisms

Formulation of Aluminum Chloride Phthalocyanine in Pluronic™ P‐123 and F‐127 Block Copolymer Micelles: Photophysical properties and Photodynamic Inactivation of Microorganisms

Novel metal-free and metallophthalocyanines containing four 21-membered pentathiadiaza macrocycles: synthesis, characterization, and study of aggregation properties

Synthesis of metal-free and metallophthalocyanines containing 18- and 21-membered macrocycles with mixed donor atoms and their metal-ion binding properties

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Formulation of Aluminum Chloride Phthalocyanine in Pluronic^™ P‐123 and F‐127 Block Copolymer Micelles: Photophysical properties and Photodynamic Inactivation of Microorganisms

Formulation of Aluminum Chloride Phthalocyanine in Pluronic^™ P‐123 and F‐127 Block Copolymer Micelles: Photophysical properties and Photodynamic Inactivation of Microorganisms