Synthesis and photophysical and electrochemical properties of novel unsymmetrical phthalocyanines with a Sudan IV moiety

2018 ◽  
Vol 22 (01n03) ◽  
pp. 112-120 ◽  
Author(s):  
İbrahim Özçeşmeci ◽  
Pınar Büyük ◽  
Ilgın Nar ◽  
Ahmet Gül
Keyword(s):  
Electrochemical Properties ◽  
Spectroscopic Data ◽  
Quantum Yields ◽  
Metal Free ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Reduction Potentials ◽  
Elemental Analyses ◽  
Sudan Iv ◽  
Ft Ir

The synthesis of novel, A[Formula: see text]B type unsymmetrical metal-free and metallophthalocyanines bearing one aza dye group Sudan IV and three nitro terminal moieties was achieved by cyclotetramerization of novel 4-((1-((E)-(2-methyl-4-((E)-[Formula: see text]-tolyldiazenyl)phenyl)diazenyl)naphthalen-2-yl)oxy)phthalonitrile and 4-nitrophthalonitrile. The new unsymmetrical metal-free and metallophthalocyanines have been characterized using elemental analyses, [Formula: see text]H NMR, FT-IR, UV-vis and mass spectroscopic data. The aggregation properties of the compounds were investigated in a concentration range of 1.0 × 10[Formula: see text] M–6.25 × 10[Formula: see text] M. General trends were also studied for fluorescence quantum yields and lifetimes of these phthalocyanine compounds in tetrahydrofuran. The fluorescence of the synthesized unsymmetrical metal-free and metallophthalocyanines is effectively quenched by 1,4-benzoquinone (BQ) in THF. In-depth investigation of the electrochemical properties showed that nitro groups extended the reduction potentials.

Synthesis and photophysical properties of a novel ethynyl zinc(II) phthalocyanine and its functionalized derivative with click chemistry

2013 ◽  
Vol 17 (06n07) ◽  
pp. 540-547 ◽  
Author(s):  
Altuğ Mert Sevim ◽  
İbrahim Özçeşmeci ◽  
Ahmet Gül
Keyword(s):  
Click Chemistry ◽  
Zinc Acetate ◽  
Spectroscopic Data ◽  
Photophysical Properties ◽  
Hexanoic Acid ◽  
Quantum Yields ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Elemental Analyses ◽  
New Compounds

The synthesis of novel, symmetrical zinc(II) phthalocyanine (ZnPc) bearing four ethynylcyclohexyloxy terminal moieties was achieved by cyclotetramerization of novel 4-(2-ethynylcyclohexyloxy) phthalonitrile in pentanol in the presence of DBU and zinc acetate without any protective/deprotective chemistry. Subsequently, this new zinc(II) phthalocyanine derivative was reacted with 6-azido-hexanoic acid under "click-chemistry" conditions to give phthalocyanine-hexanoic acid conjugates linked by 1,2,3-triazole units. The new compounds have been characterized by using elemental analyses, UV-vis, FTIR, 1 H NMR and mass spectroscopic data. The aggregation properties of the compounds were investigated in different concentrations. General trends are also described for fluorescence quantum yields and lifetimes of novel zinc derivatives in tetrahydrofuran. The fluorescence of the tetrasubstituted zinc(II) phthalocyanine complexes is effectively quenched by 1,4-benzoquinone (BQ) in THF.

Novel 7-oxy-3-(3′,4′,5′-trimethoxyphenyl)coumarin substituted zinc(II) phthalocyanines: Synthesis, characterization, photophysical and photochemical properties

2015 ◽  
Vol 19 (10) ◽  
pp. 1114-1122 ◽  
Author(s):  
Esra Nur Kaya ◽  
Mahmut Durmuş ◽  
Mustafa Bulut
Keyword(s):  
Electronic Absorption Spectra ◽  
Photophysical Properties ◽  
Quantum Yields ◽  
Oxygen Generation ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Elemental Analyses ◽  
Ft Ir ◽  
Photochemical Properties ◽  
First Time

The novel zinc(II) phthalocyanine complexes bearing tetra or octa-[7-oxy-3-(3′,4′,5′-trimethoxyphenyl)coumarin] moieties were synthesized for the first time in this study. These phthalocyanines were characterized by different spectroscopic methods such as FT-IR, 1H NMR, electronic absorption spectra, MALDI-TOF mass and elemental analyses as well. The photochemical properties such as singlet oxygen generation, photostability and photophysical properties such as fluorescence quantum yields and lifetimes were investigated in [Formula: see text],[Formula: see text]-dimethylformamide (DMF) solutions. The effect of the structure (the position and number of the coumarin groups on phthalocyanine framework) of novel phthalocyanines on these properties was also determined in this study.

Synthesis, characterization, photophysicochemical properties and theoretical study of novel zinc phthalocyanine containing four tetrathia macrocycles

2018 ◽  
Vol 22 (01n03) ◽  
pp. 77-87 ◽  
Author(s):  
Mohamad Albakour ◽  
Gülenay Tunç ◽  
Büşra Akyol ◽  
Sinem Tuncel Kostakoğlu ◽  
Savaş Berber ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Zinc Phthalocyanine ◽  
Quantum Yields ◽  
Energy Structure ◽  
Fluorescence Measurement ◽  
Oxygen Generation ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Ft Ir ◽  
Phthalocyanine Derivative

In this work, Zn(II) phthalocyanine derivative (TTU-Pc) bearing 13-membered tetrathia macrocycles was synthesized, and the novel Zn(II) phthalocyanine derivative was fully characterized by elemental analysis and general spectroscopic methods such as MALDI-TOF mass, FT-IR, UV-vis and [Formula: see text]H-NMR. The synthesized phthalocyanine derivative has quite limited solubility in most of the common organic solvents. Fluorescence measurement was conducted for this Zn(II)phthalocyanine to estimate its fluorescence quantum yields. The singlet oxygen generation ability was also examined to investigate its photosensitizer properties. General trends were described for quantum yields of fluorescence, photodegradation and singlet oxygen quantum yields of this compound. The electrochemical properties of the molecule were investigated by cyclic voltammetry (CV) and square wave voltammetry (SWV). In addition, the lowest energy structure, the electronic structure and frontier molecular orbitals were calculated in DFT and the excitation spectrum was obtained by TDDFT calculations. We found that our computational and experimental results were in agreement.

Synthesis of novel dimeric subphthalocyanines via azide-alkyne Huisgen 1,3-dipolar cycloaddition and palladiumcatalyzed Glaser–Hay coupling reactions

2017 ◽  
Vol 21 (07n08) ◽  
pp. 539-546 ◽  
Author(s):  
Özge Göktuğ ◽  
Cem Göl ◽  
Mahmut Durmuş
Keyword(s):  
Quantum Yields ◽  
Dipolar Cycloaddition ◽  
Coupling Reactions ◽  
The Novel ◽  
Oxygen Generation ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Fluorescence Measurements ◽  
Palladium Catalyzed ◽  
Ft Ir

In this study, the monomeric subphthalocyanines bearing azido (2) and terminal ethynyl (3) groups were synthesized. These subphthalocyanines were converted to their dimeric derivatives using azide-alkyne Huisgen cycloaddition and palladium-catalyzed Glaser–Hay coupling reactions subphthalocyanine (4) and (5), respectively. The novel subphthalocyanines were fully characterized by elemental analysis and general spectroscopic methods such as MALDI-TOF mass, FT-IR, UV-vis and [Formula: see text]H-NMR. All synthesized subphthalocyanines showed quite good solubility in the most of common organic solvents. The fluorescence measurements were conducted for these subphthalocyanines to estimate their fluorescence quantum yields. The singlet oxygen generation abilities were also examined to investigate their photosensitizer properties.

Silicon(IV) phthalocyanine-biotin conjugates: Synthesis, photophysicochemical properties and in vitro biological activity for photodynamic therapy

2017 ◽  
Vol 21 (07n08) ◽  
pp. 547-554 ◽  
Author(s):  
Asuman Dakoğlu Gülmez ◽  
Meltem Göksel ◽  
Mahmut Durmuş
Keyword(s):  
Photodynamic Therapy ◽  
Quantum Yields ◽  
Spectroscopic Techniques ◽  
Oxygen Generation ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Ft Ir ◽  
Human Cervical Cancer ◽  
Phthalocyanine Ring

Silicon (IV) phthalocyanines bearing one or two biotin groups on the axially positions were synthesized, and these novel phthalocyanines were characterized by elemental analysis and standard spectroscopic techniques such as FT-IR, [Formula: see text]H NMR, UV-vis and MALDI-TOF. The synthesized compounds are the first examples of axially biotin substituted silicon (IV) phthalocyanines. These phthalocyanines were designed as targeting photosensitizers for the treatment of cancer by photodynamic therapy (PDT) technique. The phthalocyanine ring was selected for its photosensitizer ability and the biotin group was selected as a targeting agent for increasing accumulation of these photosensitizers in tumor cells. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation) properties of the target silicon(IV) phthalocyanines were investigated in DMSO. The photosensitizing efficiency of the studied phthalocyanines was tested against human cervical cancer (HeLa) cells at different photosensitizer concentrations. Both axially mono- and bis-biotin substituted silicon(IV) phthalocyanines present high photocytotoxicity against HeLa cancer cells with the cell survival degree ranging from 13% to 50%. The photosensitivity and the intensity of damage were found to be directly related to the concentration of the used photosensitizers. According to the obtained results, both silicon(IV) phthalocyanine derivatives could be promising as photosensitizers for treatment of cancer by PDT technique.

Photophysical and photochemical properties of novel phthalocyanines bearing non-peripherally substituted mercaptoquinoline moiety

2012 ◽  
Vol 16 (07n08) ◽  
pp. 845-854 ◽  
Author(s):  
Göknur Yaşa ◽  
Ali Erdoğmuş ◽  
Ahmet Lütfi Uğur ◽  
M. Kasım Şener ◽  
Ulvi Avcıata ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Electronic Spectroscopy ◽  
Quantum Yields ◽  
Solubility In Water ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Good Solubility ◽  
Ft Ir ◽  
Photochemical Properties ◽  
First Time

The synthesis, photophysical and photochemical properties of nonperipherally (α) mercaptoquinoline substituted Zn(II) , TiO(IV) and Mg(II) and quaternized Zn(II) phthalocyanines are described for the first time. These complexes (2 to 5) and their precursor are characterized by elemental analysis, FT-IR, 1H NMR, electronic spectroscopy as well as mass spectroscopy. Complexes 2, 4 and 5 have good solubility in organic solvents such as CHCl3 , DCM, DMSO, DMF, THF and toluene and are not aggregated in all solvents within a wide concentration range. Complex 3 showed very good solubility in water as well as DMSO and DMF. General trends are described for singlet oxygen, photodegradation and fluorescence quantum yields of these complexes in DMSO and DMF. While complex 2 has higher singlet oxygen and fluorescence quantum yields than 3, 4 and 5, complex 4 has higher fluorescence quantum yields in DMF and DMSO than 2, 3 and 5. The effect of the solvents and metal on the photophysical and photochemical parameters of the metallophthalocyanines are also reported.

Zinc(II) and chloroindium(III) phthalocyanines bearing ethyl 7-oxy-6-chloro-4-methylcoumarin-3-propanoate groups: Synthesis, characterization and investigation of their photophysicochemical properties

2018 ◽  
Vol 22 (01n03) ◽  
pp. 266-278 ◽  
Author(s):  
Halid Kuruca ◽  
Baybars Köksoy ◽  
Begümhan Karapınar ◽  
Mahmut Durmuş ◽  
Mustafa Bulut
Keyword(s):  
Singlet Oxygen ◽  
Quantum Yields ◽  
Central Metal Atom ◽  
Central Metal ◽  
Chloride Complexes ◽  
Oxygen Generation ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Ft Ir

In this study, ethyl 7-hydroxy-6-chloro-4-methylcoumarin-3-propanoate (1), ethyl 7-(2,3-dicyanophenoxy)-6-chloro-4-methylcoumarin-3-propanoate (2), ethyl 7-(3,4-dicyanophenoxy)-6-chloro-4-methylcoumarin-3-propanoate (3), ethyl 4-chloro-5-(7-oxy-6-chloro-4-methylcoumarin-3-propanoate)phthalonitrile (4) were synthesized. The phthalonitrile derivatives (2, 3 and 4) were converted to their peripheral tetra, non-peripheral tetra and peripheral chlorocta substituted zinc(II) and chloroindium phthalocyanine derivatives. All novel compounds were characterized by elemental analysis, FT-IR, [Formula: see text]H-NMR, MALDI-TOF mass spectrometry and UV-vis spectral data. Additionally, the spectral, photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of the resulting substituted phthalocyaninatozinc(II) and indium(III) chloride complexes (5–10) were investigated in DMF, and the obtained results were compared for determination of the effects of the substituents’ positions and the variety of the central metal atom on these properties. The fluorescence quenching behavior of these phthalocyanines (5–10) were also investigated using 1,4-benzoquinone as a quencher. The obtained ethyl 7-oxy-6-chloro-4-methylcoumarin-3-propanoate bearing phthalocyaninatozinc(II) (5, 7 and 9) and indium(III) chloride (6, 8 and 10) complexes showed excellent solubility in most organic solvents. They produced high singlet-oxygen and showed appropriate photodegradation which is very important for photodynamic therapy applications.

Five-nuclear phthalocyanine complex bearing terpyridine zinc complex: Synthesis, and photophysicochemical studies

2018 ◽  
Vol 22 (01n03) ◽  
pp. 181-188 ◽  
Author(s):  
Pinar Sen ◽  
S. Zeki Yildiz ◽  
Göknur Yasa Atmaca ◽  
Ali Erdogmus
Keyword(s):  
Mass Spectroscopy ◽  
Zinc Complex ◽  
Quantum Yields ◽  
Spectroscopic Techniques ◽  
Oxygen Production ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Phthalocyanine Complex ◽  
Ft Ir ◽  
C Nmr

The context of this study is based on the synthesis of tetrakis{4-(2-([2,2[Formula: see text]:6[Formula: see text],2[Formula: see text]-terpyridine]Zn(II)-4[Formula: see text]-yl(methyl)amino)ethoxy)}phthalocyaninato zinc (II) (3) bearing four terpyridine-Zn(II) complexes that are directly linked through oxygen bridges to the macrocyclic core in order to create new supramolecular assemblies. The target phthalocyanine (3) was obtained by cyclotetramerization reaction of terpyridine-Zn (II) complex substituted phthalonitrile (2). All novel compounds synthesized in this study were fully characterized by general spectroscopic techniques such as FT-IR, UV-vis, and [Formula: see text]H-NMR, [Formula: see text]C-NMR, elemental analysis and mass spectroscopy. Spectral, photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen production and photodegradation under light irradiation) properties of newly synthesized phthalonitrile (2) and its phthalocyanine derivative (3) as five nuclear phthalocyanine were investigated in DMSO solutions.

scholarly journals Synthesis, Characterization, and Antimicrobial Activity of Methyl-2-aminopyridine-4-carboxylate Derivatives

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
S. Nagashree ◽  
P. Mallu ◽  
L. Mallesha ◽  
S. Bindya
Keyword(s):  
Antimicrobial Activity ◽  
Spectral Studies ◽  
H Nmr ◽  
Chemical Structures ◽  
Elemental Analyses ◽  
Ft Ir

A series of methyl-2-aminopyridine-4-carboxylate derivatives,3a–f,were synthesized in order to determine theirin vitroantimicrobial activity. The chemical structures of the synthesized compounds were confirmed by elemental analyses, FT-IR, and1H NMR spectral studies. Among the synthesized compounds,3cand3dshowed good antimicrobial activity compared to other compounds in the series.

scholarly journals Synthesis and Characterization of Trivalent Cerium Complexes of p-tert-Butylcalix[4,6,8]Arenes: Effect of Organic Solvents

2013 ◽  
Vol 2013 ◽  
pp. 1-9 ◽  
Author(s):  
Md. Hasan Zahir
Keyword(s):  
Organic Solvents ◽  
Electronic Absorption ◽  
Electronic Absorption Spectra ◽  
H Nmr ◽  
Protic Solvents ◽  
Elemental Analyses ◽  
Ft Ir ◽  
X Ray Absorption ◽  
Molar Extinction Coefficients

Reaction of Ce3+with p-tert-butylcalix[n]arene (n=4,6,8) yields purple crystalline complexes structurally as [Ce(p-tert-butylcalix[4]arene-3H)2(NO3)(DMF)x](2 −x)DMF (1), [Ce(p-tert-butylcalix[6]arene-4H)2(NO3)(DMF)x](3 −x)DMF (2), and [Ce(p-tert-butylcalix[8]arene-7H)2(NO3)(DMF)6] (3), whereDMF=N,N-dimethylformamide. The properties and coordination characteristics of the three calixarene complexes were determined by elemental analyses, electronic absorption, X-ray absorption spectroscopy (EXAFS), TG-DTA, FT-IR, SEM, and1H-NMR spectroscopy. The effect of various organic solvents on complexes1,2, and3has been discussed based on results from electronic absorption spectra. The polar protic solvents showed the most significant molar extinction coefficients in comparison with those of nonpolar and polar aprotic solvents. The Ce3+ions in the complexes are proved to combine with the ligand phenolic groups, oxygen atoms of DMF molecules, and/or OH−ions.

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