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Asymmetrically tetra-substituted phthalocyanine derivatives: synthesis, photophysical and photochemical properties
(Springer, 2022) Dilber, Gulsev; Nas, Asiye; Piskin, Mehmet; Durmus, Mahmut
The syntheses of highly soluble asymmetrically substituted metal free and zinc phthalocyanine derivatives bearing three 4-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenoxy) and one 4-(2-(benzo[d]thiazol-2-yl)phenoxy) groups or bearing one 4-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenoxy) and three 4-(2-(benzo[d]thiazol-2-yl)phenoxy) groups were reported for the first time in this study. The successful synthesis of phthalocyanines was achieved through the common statistical condensation method utilizing two different phthalonitriles named as 4-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenoxy)phthalonitrile and 4-(2-(benzo[d]thiazol-2-yl)phenoxy)phthalonitrile. The asymmetrical phthalocyanines were characterized by spectroscopic methods. Moreover, the aggregation behavior, photophysical and photochemical properties of the substituted A(3)B type asymmetrical metal free and Zn (II) phthalocyanines were investigated in DMF. The asymmetrical Zn (II) phthalocyanine complexes produced highly singlet oxygen and appropriate fluorescence behavior in DMF suggesting that they can be suitable candidates as Type II photosensitizers in photodynamic therapy (PDT) applications.
Determination of photophysical, photochemical and spectroscopic properties of novel lead(II) phthalocyanines
(Pergamon-Elsevier Science Ltd, 2020) Piskin, Mehmet; Ozturk, Omer Faruk; Odabas, Zafer
This study presents the synthesis and characterization of novel peripheral and non-peripheral tetra-2,6-dimethoxyphenoxy substituted lead(II) phthalocyanines. They were characterized by elemental analysis, IR, UV-vis, fluorescence, H-1 NMR, C-13 NMR and MALDI-TOF mass spectroscopic techniques, as well as thermogravimetric analysis. Their spectroscopic, photophysical and photochemical properties were studied in dimethylsulfoxide and compared with the above-mentioned properties of lead(II) phthalocyanines containing different substituents reported in the literature. Novel phthalocyanines can be good candidates as photosensitizers for photocatalytic reactions because they possess properties that are important for Type II mechanics, such as low photostability, sufficient singlet oxygen production, high solubility and non-aggregation behavior in commonly known organic solvents. (C) 2020 Elsevier Ltd. All rights reserved.
Do the positions of trimethyl groups on phthalocyanine photosensitizers improve their photochemical and photophysical properties?
(Elsevier Science Sa, 2017) Cetinkaya, Mehmet; Piskin, Mehmet; Altun, Selcuk; Odabas, Zafer; Durmus, Mahmut
The synthesis of novel highly soluble and non-aggregated metal-free and zinc(II) phthalocyanines containing four 2,3,5-trimethylphenoxy groups was achieved by starting phthalonitrile compounds. The phthalocyanines were characterized by elemental analysis, infrared, ultraviolet-visible and matrix assisted laser desorption/ionization time-of-flight mass spectroscopic techniques. Their photochemical and photophysical properties were also investigated in N,N-dimethylformamide. In addition, the influences of position of methyl groups on phenoxy unit and nature of metal in phthalocyanine cavity on photophysical and photochemical properties were investigated by comparing with previous analogues (phthalocyanines with 2,3,6-trimethylphenoxy and 2,4,6-trimethylphenoxy groups). (C) 2016 Elsevier B.V. All rights reserved.
Efficient singlet oxygen generation by triptycene substituted A3B type zinc(II) phthalocyanine photosensitizers
(Pergamon-Elsevier Science Ltd, 2016) Al-Sohaimi, Bandar R.; Piskin, Mehmet; Ghanem, Bader S.; Al-Raqa, Shaya Y.; Durmus, Mahmut
A(3)B type unsymmetrical 8,11,15,18,22,25-hexadecyl-2,3-(9,10-diocty1-6,7-dimethoxy-2,3-dioxytriptycene) (11) and 8,11,15,18,22,25-hexadecyl-2,3-(9,10-diundecy1-6,7-dimethoxy-2,3-dioxytriptycene) (12) zinc(II) phthalocyanines were synthesized for the first time. Their photophysical and photochemical properties were investigated as solutions in toluene and obtained values were compared with unsubstituted zinc(II) phthalocyanine for determination of substitution effect. Both newly synthesized phthalocyanines showed high singlet oxygen generation making them good candidates as photosensitizers for photocatalytic-reactions. (C) 2015 Elsevier Ltd. All rights reserved.
Enhancing photophysical and photochemical properties of zinc(II) phthalocyanine dyes by substitution of triptycene moieties
(Elsevier, 2016) Al-Sohaimi, Bander Roshadan; Piskin, Mehmet; Aljuhani, Ateyatallah; Al-Raqa, Shaya Y.; Durmus, Mahmut
The symmetrical zinc(II) phthalocyanines conjugated with 9,10-dioctyl-6,7-dimethoxy-2,3-dioxytriptycene or 9,10-diundecyl-6,7-dimethoxy-2,3-dioxytriptycene moieties were synthesized in this study. These novel phthalocyanines were characterized by standard characterization techniques such as 1HNMR, FT-IR, UV-vis, Mass and Elemental Analysis. All these phthalocyanines showed highly solubility and formed non-aggregated monomeric species in most of the organic solvents. Their photochemical properties such as singlet oxygen, and photodegradation quantum yields, and photophysical properties including fluorescence quantum yields and lifetimes were investigated in toluene. The fluorescence quenching behavior of the studied zinc(II) phthalocyanines by the addition of 1,4-benzoquinone were also described in toluene. (C) 2016 Elsevier B.V. All rights reserved.
First investigation on the photophysical and photochemical properties of azo-bridged phthalocyanine photosensitizers
(Elsevier Science Bv, 2016) Sahin, Safinaz; Piskin, Mehmet; Altun, Selcuk; Durmus, Mahmut; Odabas, Zafer
Novel azo-bridged indium(III) acetate phthalocyanine was synthesized by cyclotetramerization reaction of (E)-4-((2,5-dimethoxyphenyl)diazenyl)phthalonitrile. This phthalocyanine was fully characterized by FT-IR, H-1-NMR, UV-vis and MALDI-TOF mass spectroscopic techniques and elemental analyses as well. Additionally, the photophysical and photochemical properties of this phthalocyanine was investigated for the first time. The obtained results were compared with azo-bridged zinc(II) and metal-free phthalocyanine counterparts for determination of central metal effect on these properties. These results were also compared with unsubstituted zinc(II) and indium(III)acetate phthalocyanines for determination of substitution effect on the photophysical and photochemical properties. (C) 2016 Elsevier B.V. All rights reserved.
Metal or metal-free phthalocyanines containing morpholine substituents: synthesis, spectroscopic and photophysicochemical properties
(Taylor & Francis Ltd, 2022) Demirbas, Umit; Piskin, Mehmet; Durmus, Mahmut; Kantekin, Halit
The phthalonitrile (3) and its peripherally tetra 4-(3-morpholinophenoxy) substituted metal-free (4), lead(II) (5) and zinc(II) (6) phthalocyanine derivatives were synthesized. The structures of 3-6 were confirmed by FT-IR, H-1-NMR, MALDI-TOF mass, UV-vis and fluorescence spectral data. The solubility and aggregation behaviors of 4-6 were determined in dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), tetrahydrofuran (THF), chloroform (CHCl3) and dichloromethane (CH2Cl2). The observed sharp absorptions were evidence of formation of non-aggregated phthalocyanine species at the studied concentration. The effects of the substituent and central metal ions (metal-free, zinc or lead) on spectroscopic and photophysicochemical properties were determined. Their photophysicochemical properties such as fluorescence quantum yields and lifetimes, singlet oxygen generation and photodegradation quantum yields were investigated in DMSO. The fluorescence spectra of metal-free (4) and lead(II) (5) phthalocyanines were not recorded due to negligible fluorescence emissions of these phthalocyanines. The zinc(II) phthalocyanine (6) had 0.17 fluorescence quantum yield (phi(F)) and 1.42 fluorescence lifetime (tau(F)). The phthalocyanines (4-6) had 0.18, 0.41, 0.52 singlet oxygen quantum yields (phi(Delta)) and 0.51, 3.90, 0.46 photodegradation quantum yields (phi(Delta)), respectively. The zinc(II) phthalocyanine (6) in particular could be a potential Type II photosensitizer candidate for photodynamic therapy in cancer treatment.
Metal-free, zinc(II) and lead(II) phthalocyanines functioning with 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate groups: Synthesis and investigation of photophysical and photochemical properties
(Elsevier Science Sa, 2016) Demirbas, Umit; Piskin, Mehmet; Barut, Burak; Bayrak, Riza; Durmus, Mahmut; Kantekin, Halit
In this study, the synthesis and characterization of 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate substituted novel phthalonitrile compound and its peripherally substituted zinc(II) lead(II) and metal-free phthalocyanine derivatives were performed for the first time. This novel compounds were characterized by obtained data from general spectroscopic methods such as FT-IR, H-1 NMR, C-13 NMR and mass. The photophysical and photochemical properties of these phthalocyanines were investigated in N,N-dimethylformamide solutions for determination of their photosensitizing abilities in photocatalytic applications such as photodynamic therapy. The lead(II) phthalocyanine complex did not produce any fluorescent in N,N-dimethylformamide because of the heavy atom effect of bigger lead atom. The fluorescence quantum yields of studied zinc(II) and metal-free phthalocyanines were found to quite higher than unsubstituted zinc(II) phthalocyanine due to substitution of the phthalocyanine skeleton. The influence of substituent and variety of the central metal ions on spectroscopic, photophysical and photochemical properties were also determined and compared. (C) 2016 Elsevier B.V. All rights reserved.
New peripherally and non-peripherally tetra-substituted metal-free, magnesium(II) and zinc(II) phthalocyanine derivatives fused chalcone units: Design, synthesis, spectroscopic characterization, photochemistry and photophysics
(Elsevier Science Sa, 2018) Kantekin, Halit; Yalazan, Halise; Kahriman, Nuran; Ertem, Beytullah; Serdaroglu, Vildan; Piskin, Mehmet; Durmus, Mahmut
Chalcone containing new peripherally and non-peripherally tetra-substituted metal-free and metallophthalo-cyanine derivatives were designed and synthesized (Schemes 1 and 2). The structures of chalcone-phthalocyanines were characterized by a combination of common spectroscopic techniques such as LC-MS/MS (for new phthalonitrile derivative 3a), ground state electronic absorption spectra (for all new phthalocyanines), H-1 NMR spectroscopy (for all new compounds), C-13 NMR spectroscopy (for new phthalonitrile and metal-free phthalocyanine derivatives), Fourier transform infrared (FT-IR with ATR sampling accessory) (for all new compounds) and MALDI-TOF mass spectral data (for all new phthalocyanines and new phthalonitrile derivative 3b) as well as elemental analysis. In addition, the effects of the presence of different kinds of metal ions [magnesium(II) or zinc (II)] in the phthalocyanine core and the effects of the introduction of (3,4-dimethoxyphenyl)-3-oxoprop-1en-1-yl)phenoxy units at both peripheral and non-peripheral positions of the phthalocyanine skeleton on photophysical and photochemical properties of the new substituted magnesium(II) and zinc(II) phthalocyanines have also been examined in DMF. The obtained results were compared with each other and with unsubstituted magnesium(II) and zinc(II) phthalocyanines. All newly synthesized phthalocyanines are soluble in common organic solvents as well as no type of aggregation was observed in these solvents. Moreover; the chalcone fused magnesium(II) and zinc(II) phthalocyanines also showed excellent fluorescence properties. Specifically, the new non-peripheral zinc(II) and magnesium(II) chalcone-phthalocyanines have the remarkable potential to be used as Type II photosensitizers for the treatment of cancer in PDT owing to their good singlet oxygen and appropriate photodegradation quantum yields. Since chalcones and their derivatives show a broad range of biological and pharmaceutical activities, these products are promising candidates for various applications, particularly as photosensitizers for photodynamic therapy in combination with fluorescence imaging.
New peripherally and non-peripherally tetra-substituted water soluble zinc phthalocyanines: Synthesis, photophysics and photochemistry
(Elsevier Science Sa, 2015) Cakir, Volkan; Cakir, Dilek; Piskin, Mehmet; Durmus, Mahmut; Biyiklioglu, Zekeriya
The synthesis and photochemical properties of peripherally and non-peripherally 1,3-bis[3-(dimethy-lamino)phenoxy]prop-2-oxy tetra-substituted zinc phthalocyanines (2a and 3a) and their quaternized derivatives (2b and 3b) were reported in this study. Photochemical properties of quaternized ionic zinc (II) phthalocyanines (2b and 3b) were investigated in both dimethyl sulfoxide (DMSO) and aqueous solutions, while non ionic derivatives were only studied in DMSO. The quaternized compounds exhibit excellent solubility in water, making them potential photosensitizers for use in photodynamic therapy (PDT) of cancer. This study also showed that the water-soluble quaternized Zn(II) phthalocyanines strongly bind to blood plasma proteins such as bovine serum albumin (BSA). On the other hand, the interactions of the novel water soluble phthalocyaines with DNA were also examined. (C) 2015 Elsevier B.V. All rights reserved.
Novel 2,6-dimethoxyphenoxy alpha substituted phthalocyaninato metal complexes: Electrochemistry, In situ spectroelectrochemistry and oxygen electrocatalysis
(Elsevier Science Sa, 2022) Orman, Efe Baturhan; Yazar, Zuhal; Piskin, Mehmet; Odabas, Zafer; Ozkaya, Ali Riza
Non-peripherally tetra-2,6-dimethoxyphenoxy substituted Co(II) 3, Fe(II) 4, Mn(III) 5, and Ni(II) 6 phthalocyanines were prepared by refluxing the n-pentanol solution of their metal-free analogue H2Pc 2, (obtained by using 3-(2,6-dimethoxyphenoxy)phthalonitrile), metal salts (Co(CH3COO)2.4 H2O, Fe(CH3COO)2, Mn (CH3COO)2.4 H2O or NiCl2) and 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU) as the catalyst under N2 atmosphere for 2 h. The molecular structure of metallophthalocyanines 3-6 were explained by common methods which are elemental analysis, MALDI-TOF mass, FTIR, and UV-Vis spectroscopies. The complexes are well dissolved in various solvents (dichloromethane, tetrahydrofuran, dimethylsulfoxide, dimethylformamide, and toluene. Electrochemical redox, electrocatalytic oxygen reducing and electrocolorimetric properties of the phthalocyanine complexes were also measured by voltammetric and in situ UV-Vis spectroelectrochemical techniques. The phthalocyanine complexes displayed highly reversible sequential one-electron redox processes occurring at metal and/or phthalocyanine ring. The association of these processes with net colour changes pointed out their functionality as electrochromic material. Furthermore, the phthalocyanine complexes 3-5 and especially Fe(II)Pc 4, showed striking electrocatalytic oxygen reducing activity, owing to the metal centres with redox activity, increasing their interplay with the O2 molecule.
Photophysical and photochemical properties and comparison of tolyl and tosyl coumarin-bearing phthalocyanines
(Elsevier, 2023) Kazancicok, Zehra; Guler, Hatice Esar; Ozdemir, Mucahit; Piskin, Mehmet; Bulut, Mustafa; Yalcin, Bahattin; Salan, Umit
In this study, peripheral and non-peripherally substituted Zn(II) phthalocyanine complexes were synthe-sized from 7-hydroxy-3-(p-tolyl)coumarin and 7-hydroxy-3-(p-tosyl)coumarin compounds. The synthe-sized new compounds were characterized using elemental analysis, FT-IR, UV-Vis, Fluorescence 1 HNMR spectroscopy and MALDI-TOF mass spectrometry. All the synthesized phthalocyanine complexes showed good solubility in organic solvents such as acetone, dichloromethane, chloroform, pyridine, and ethyl acetate. Fluorescent quenching behavior was investigated using 1,4-benzoquinone and potassium io-dide as a quencher. The photophysical (fluorescent quantum yields and lifetimes) and photochemical (single oxygen and photodegradation quantum yields) properties of these new phthalocyanines were examined in dimethyl sulfoxide. Phthalocyanine complexes containing 7-hydroxy-3-(p-tolyl)coumarin had higher singlet oxygen quantum yields than phthalocyanine complexes containing 7-hydroxy-3-(p- tosyl)coumarin. Phthalocyanines to which coumarins are peripherally bound were more advantageous than their non-peripherally bound derivatives. As a result of their photophysical and photochemical prop-erties, coumarin-phthalocyanine complexes containing tolyl-/tosyl-groups can be used as photosensitiz-ing candidates in photodynamic therapy and can be developed with targeted modifications.(c) 2022 Elsevier B.V. All rights reserved.
Phthalocyanine photosensitizers with bathochromic shift, of suitable brightness, capable of producing singlet oxygen with effective efficiency
(Elsevier Science Sa, 2023) Piskin, Mehmet
In this study, novel 3-(2,3-dimethoxyphenoxy)phthalonitrile 2 and its non-peripheral tetra-2,3-dimethox-yphenoxy substituted metal-free phthalocyanine 3 compounds were synthesized. Then, the magnesium(II), zinc (II), and indium(III) acetate phthalocyanine complex derivatives (4-6) of compound 3 were synthesized using the corresponding metal salts by the template effect. The structures of novel phthalonitrile derivative 2 and its metal-free phthalocyanine compounds 3 as well as different metal-containing phthalocyanine complexes (4-6) were characterized by elemental analysis, FTIR, UV-vis, 1H-NMR, and MALDI-TOF mass spectroscopic tech-niques. The phthalocyanines (3-6) can dissolve well in different polar protic, polar aprotic, and non-polar solvent types without aggregation, with maximum absorption intensity and bathochromic effect. Photophysicochemical properties of the phthalocyanines (3-6) in dimethyl sulfoxide and important spectral parameter values such as molar extinction coefficient, oscillator strength, and electrical dipole strength were determined, and they were also compared with each other and with their unsubstituted counterparts. It was determined that the phthalo-cyanines (3-6) have suitable and sufficient fluorescence quantum yields, fluorescence lifetimes, fluorescence brightness, and other photophysical properties, as well as singlet oxygen generation, phototoxic power, and photostability properties. The phthalocyanines (3-6), particularly zinc(II) and indium(III) acetate phthalocya-nines have remarkable potential for use as Type II photosensitizers for cancer therapy in photodynamic therapy. The phthalocyanines (3-6) may be promising candidates for various applications as photosensitizers for photodynamic therapy, especially in combination with fluorescent imaging.
Spectroscopic and electrochemical behavior of the novel tetra-2-methyl-pyrazinoporphyrazines
(Elsevier Science Bv, 2017) Piskin, Mehmet; Ozturk, Naciye; Durmus, Mahmut
This study presents the synthesis and characterization of novel metal-free (H2Pc) and metallo porphyrazines (magnesium(II) (MgPz), copper(II) (CuPz), iron(II) (FePz), manganese(II) (MnPz) and nickel(II) (NiPz)) substituted with four 2-methylpyrazine groups on the peripheral positions. The spectroscopic properties of newly synthesized porphyrazines were investigated. The electrochemical behaviors of these porphyrazines were also determined in DMSO solution by cyclic voltammetry (CV) and square wave voltammetry (SWV) methods on edge plane pyrolytic graphite electrode (EPPG) electrode. (C) 2017 Published by Elsevier B.V.
Spectroscopic and photophysicochemical properties of zinc(II) phthalocyanine substituted with benzenesulfonamide units containing schiff base
(Ios Press, 2022) Oncul, Gulen Atiye; Ozturk, Omer Faruk; Piskin, Mehmet
In this study, compounds (E)-4-((5-bromo-2-hydroxy-3-methoxybenzylidene)amino)-N-(pyridin-2-yl)benzenesul-fonamide 1, (E)-4-((5-bromo-2-(3,4-dicyanophenoxy)-3-methoxybenzylidene)amino)-N-(pyridin-2-yl)benzenesulfonamide 2 and, complex 2(3),9(10),16(17),23(24)-tetra-[(E)-4-((5-bromo-3-methoxy-2-(lambda(1)-oxidanyl)benzylidene)amino)-N-(pyridine-2-yl)benzenesulfonamide]phthalocyaninato zinc(II) 3 were synthesized for the first time. Their structures (1-3) were characterized by spectroscopic methods such as FTIR, H-1 NMR,C-13 NMR, UV-vis, MALDI-TOF mass spectra and elemental analysis. The spectroscopic, aggregation, photophysical and photochemical properties of zinc(II) phthalocyanine 3 in dimethyl sulfoxide were investigated and the effects on the above-mentioned properties were reported as a result of the presence of benzenesulfonamide derivatives containing different bioactive groups, in their peripheral positions. In addition, its above-mentioned properties were also reported by comparing different species with those of their substituted and/or unsubstituted counterparts. The zinc(II) phthalocyanine 3 can be a potential photosensitizer candidate in photodynamic therapy, which is an effective alternative therapy in cancer treatment, due to its good solubility in commonly known solvents and monomeric species, as well as its adequate and favorable fluorescence, singlet oxygen production and photostability.
Spectroscopic, photophysical and photochemical properties of newly metallo-phthalocyanines containing coumarin derivative
(Elsevier, 2020) Capkin, Aylin; Piskin, Mehmet; Durmus, Mahmut; Bulut, Mustafa
The new, well-soluble and non-aggregated peripheral or non-peripheral tetra-ethyl 7-oxy-4,8-dimethylcoumarin-3-propanoate substituted magnesium (II), zinc (II) and indium (III) acetate phthalocyanines were synthesized. They were characterized by widely known spectroscopic methods such as UV-vis, IR, MALDI-TOF Mass, H-1 NMR spectroscopies and elemental analysis. Photophysical and photochemical properties were studied in N, N-dimethylformamide to determine the usability of each of these phthalocyanines as photosensitizers. The influences of the position and presence of the coumarin derivative at the phthalocyanine skeleton and metal' nature in the phthalocyanine cavity on photophysical and photochemical properties were investigated by comparing with previous analogues (magnesium, zinc, and indium phthalocyanines containing coumarin derivative with different functional groups). The spectroscopic, photophysical, photochemical data and results obtained for each of these phthalocyanines show that they may have the potential to be used as photosensitizers in photodynamic therapy. (c) 2020 Elsevier B.V. All rights reserved.
Synthesis, characterisation, photophysical and photochemical properties of free-base tetra-(5-chloro-2-(2,4-dichlorophenoxy) phenoxy)phthalocyanine and respective zinc(II) and lead(II) complexes
(Elsevier Science Sa, 2017) Demirbas, Umit; Piskin, Mehmet; Akcay, Hakki Turker; Barut, Burak; Durmus, Mahmut; Kantekin, Halit
In this study, novel peripherally tetra-(5-chloro-2-(2,4-dichlorophenoxy)phenol) substituted metal-free (4), zinc(II) (5) and lead(II) (6) phthalocyanine derivatives were synthesised. The novel phthalocyanines (4-6) were characterised by general spectroscopic methods such as IR, H-1 NMR, UV-vis, mass spectrometry and elemental analysis. Once the solubilities of the compounds were investigated, it was noticed that they have excellent solubility and did not tend to aggregation behaviour in common solvents. The photophysical and photochemical properties of novel phthalocyanines (4-6) were investigated in dimethysulfoxide. The effects of substituted 5-chloro-2-(2,4-dichlorophenoxy)phenoxy group and central metal ion [zinc(II)/lead(II)] on photophysical and photochemical properties of the novel phthalocyanines have also been examined, and the results were compared with unsubstituted zinc (II) phthalocyanine. According to photophysical and photochemical investigation results, it was observed that the novel phthalocyanines (4-6) have a potential for PDT application. (C) 2016 Elsevier B.V. All rights reserved.
Synthesis, characterization and investigation of the photophysical and photochemical properties of highly soluble novel metal-free, zinc(II), and indium(III) phthalocyanines substituted with 2,3,6-trimethylphenoxy moieties
(Royal Soc Chemistry, 2015) Gurel, Ekrem; Piskin, Mehmet; Altun, Selcuk; Odabas, Zafer; Durmus, Mahmut
This work presents the synthesis and characterization of metal-free, zinc((II)), and indium((III)) acetate phthalo-cyanines substituted with 2,3,6-trimethylphenoxy groups at the peripheral and non-peripheral positions. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of these novel phthalocyanines and un-substituted zinc((II)) and indium((III)) acetate phthalocyanines were investigated in dimethylformamide solution. The effects of the types of substituents and their positions and the variety of central metal ions on the phthalocyanine core on their spectroscopic, photophysical and photochemical properties were also determined. The studied 2,3,6-trimethylphenoxy substituted metal-free, zinc((II)) and indium((III)) acetate phthalocyanines especially indium((III)) acetate derivatives exhibited appropriate photophysical and photochemical properties such as high singlet oxygen generation and these phthalocyanines can be potential Type II photosensitizers for photodynamic therapy in cancer applications.
Synthesis, characterization, photophysical, and photochemical properties of novel zinc(II) and indium(III) phthalocyanines containing 2-phenylphenoxy units
(Elsevier Science Bv, 2016) Ali, Haytham Elzien Alamin; Piskin, Mehmet; Altun, Selcuk; Durmus, Mahmut; Odabas, Zafer
The synthesis of highly soluble and non-aggregated peripherally/non-peripherally Zn and In(OAc) phthalocyanines was achieved by 3-/ and 4-(2-phenylphenoxy)phthalonitrile as starting materials. The novel compounds were characterized by elemental analyses, FT-IR, H-1-NMR (for phthalonitriles), UV-vis and MALDI-TOF mass (for Pcs) spectroscopic techniques. Additionally, photophysical, photochemical and spectral properties of the phthalocyanines were reported. Especially, the indium(OAc) phthalocyanines showed good singlet oxygen quantum yields in DMSO and they can be appropriate candidates as Type II photosensitizers in photodynamic therapy (PDT) applications. (C) 2015 Elsevier B.V. All rights reserved.
Synthesis, photophysical and photochemical properties of novel phthalocyanines substituted with triptycene moieties
(Pergamon-Elsevier Science Ltd, 2015) Ghanem, Bader S.; Piskin, Mehmet; Durmus, Mahmut; El-Khouly, Mohamed E.; Al-Raqa, Shaya Y.
New metal-free and zinc(II) phthalocyanines containing four triptycene moieties were synthesized and characterized by H-1 NMR, mass, IR, electronic spectroscopies and elemental analysis as well. The steady-state absorption spectra of the investigated compounds exhibited the main absorption bands in the visible region, at around 700 nm. The fluorescence spectra and quantum yields were recorded by steady-state emission measurements. The powerful nanosecond laser flash photolysis technique was employed to record the transient absorption spectra of the long-lived triplet states of the investigated compounds. The singlet oxygen generation and photodegradation properties of the target phthalocyanines under light irradiation were also investigated in tetrahydrofuran solution. (C) 2015 Elsevier Ltd. All rights reserved.

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