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1.
Nilgün KABAY Yasemin BAYGU Metin AK zzet KARA EsraNur KAYA Mahmut DURMU Yaar G
K 《Turkish Journal of Chemistry》2021,45(1):143
The current study describes the synthesis, electrochemical, computational, and photochemical properties of octa (3-hydroxypropylthio) substituted cobalt (II) ( 4 ), copper (II) ( 5 ), nickel (II) ( 6 ) and zinc(II) ( 7 ) phthalocyanine derivatives. These novel compounds were characterized by elemental analysis,1H,13C NMR, FT-IR, UV-Vis, and MS. The redox behaviors of these metallo-phthalocyanines were investigated by the cyclic voltammetric method. The optimized molecular structure and gauge-including atomic orbital (GIAO)1H and13C NMR chemical shift values of these phthalocyanines in the ground state had been calculated by using B3LYP/6–31G(d,p) basis set. The outcomes of the optimized molecular structure were given and compared with the experimental NMR values. The photochemical properties including photodegradation and singlet oxygen generation of zinc(II) phthalocyanine were studied in DMSO solution for the determination of its photosensitizer behaviors. 相似文献
2.
Gülsev Dilber Mahmut Durmuş Halit Kantekin Volkan Çakır 《Journal of organometallic chemistry》2011,696(15-16):2805-2814
The synthesis and characterization of peripherally tetra-biphenyl-4-yl-methoxy substituted metal-free (4), Ni(II) (5), Cu(II) (6), Zn(II) (7), Co(II) (8) and Pb(II) (9) phthalocyanine derivatives are reported. These new phthalocyanine derivatives show the enhanced solubility in organic solvents and they have been characterized by a combination of IR, 1H NMR, 13C NMR, UV–vis, mass spectral data, elemental analysis and thermal analysis methods (TG/DTA). The photophysical (fluorescence quantum yield and lifetime) and photochemical (singlet oxygen generation and photodegradation quantum yield) properties of tetra-biphenyl-4-yl-methoxy substituted zinc (II) phthalocyanine derivative (7) are also investigated. The fluorescence of this phthalocyanine derivative (7) is effectively quenched by addition of 1,4-benzoquinone (BQ). 相似文献
3.
Phthalocyanines with four biphenyl-malonic ester groups on the periphery were synthesized by cyclotetramerization of 4-(1,1-dicarbethoxy-2-(4-biphenyl)-ethyl)-phthalonitrile. The new compounds were characterized by elemental analyses, FT-IR, 1H NMR, 13C NMR, UV–Vis, and MASS spectral data. Electrochemical behaviors of novel Co(II), Cu(II), and Pd(II) phthalocyanines were investigated by cyclic voltammetry, potential differential pulse voltammetry, and applied potential chronocoulometry techniques. While Cu(II) and Pd(II) phthalocyanines give up to four common phthalocyanine ring reductions, Co(II) phthalocyanine gave two ligand-centered and two metal-centered redox processes. HOMO–LUMO gap of the complexes are comparable with the reported MPc papers. 相似文献
4.
A novel alcohol-soluble ionophore ligand and its non-peripherally tetrasubstituted functional 1,8,15,22-tetrakis(6-hydroxyhexylsulfanyl) metallophthalocyanines M[Pc(α-SC6H12OH)4] (M = Cu(II), Zn(II), Co(II); Pc = phthalocyanine) are reported. The aggregation and cation binding behaviors of the phthalocyanine compounds in the presence of soft AgI and PdII metal ions were investigated by using UV–Vis spectroscopy. The new compounds have been characterized by elemental analysis, IR, 1H, 13C NMR, UV/Vis spectroscopy, ESI and MALDI–TOF–MS mass spectra. Voltammetric and in-situ spectroelectrochemical studies show that while copper and zinc phthalocyanine complexes give well-defined ring-based reduction and oxidation processes, the cobalt phthalocyanine gives both metal-based and ring-based redox processes which have reversible and diffusion controlled character. 相似文献
5.
Functional zinc(II) phthalocyanines bearing Schiff base complexes as oxidation catalysts for bleaching systems
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Oxidation catalysis is used to increase the performance of hydrogen peroxide in laundry bleach applications. Bleach catalysts provide cost‐effective, energy‐saving and environmentally friendly bleach systems yielding perfect stain removal at lower temperatures. This comparative study is based on the synthesis of bis[bis(salicylhydrazonephenoxy)manganese(III)] phthalocyaninatozinc(II) ( 2 ), bis[bis(salicylhydrazonephenoxy)cobalt(III)] phthalocyaninatozinc(II) ( 3 ) and bis[bis(salicylhydrazonephenoxy)iron(III)] phthalocyaninatozinc(II) ( 4 ) as tri‐nuclear complexes consisting of two Schiff base complexes substituting a zinc phthalocyanine. Complexion on the periphery to obtain complexes 2 , 3 , 4 was performed through the reaction of a Schiff base‐substituted phthalocyanine using MnCl2?4H2O, CoCl2?6H2O or FeCl3?6H2O salts in basic condition in dimethylformamide. Fourier transform infrared, 1H NMR, 13C NMR, UV–visible, inductively coupled plasma optical emission and mass spectra were applied to characterize the prepared compounds. The bleach performances of the three phthalocyanine compounds 2 , 3 , 4 were examined by the degradation of morin as hydrophilic dye. The degradation progress in the presence of catalysts 2 , 3 , 4 /H2O2 combination in aqueous solution was investigated using an online spectrophotometric method. It was found that the catalysts 2 , 3 , 4 exhibited better bleaching performance at 25 °C than tetraactylethylethylenediamine as bleach activator used in powder detergent formulations for stain removal. Copyright © 2015 John Wiley & Sons, Ltd. 相似文献
6.
A new trans-2,2′-azoquinoxaline bridged bisphthalocyanine was synthesized from the corresponding quinoxaline-2(1H)-one oxime, which can be obtained by the reaction of s-trans-chloroethanedial with 2-(3,4-diaminophenoxy)-9,16,23-tri(hexylthio)phthalocyanine zinc(II). 2-(3,4-Diaminophenoxy)-9,16,23-tri(hexylthio)phthalocyanine zinc(II) was synthesized by reduction of 2-(4-amino-3-nitrophenoxy)-9,16,23-tri(hexylthio)phthalocyanine zinc(II). Novel compounds were characterized by elemental analysis, UV/vis, IR and 1H NMR spectroscopy. The conductivity and the humidity sensing properties of spin coated films of these compounds were investigated by measuring the complex impedance spectra at different humidities. Films of the final product show up to 103 orders of magnitude higher conductivity than the starting and intermediate compounds. The results indicate that the presence of water vapour always leads to a drop in the real and imaginary part of the complex impedance. At room temperature, the capacitance of the films exhibits reversible increase with relative humidity, which makes these films attractive for humidity sensing applications. 相似文献
7.
《Journal of Coordination Chemistry》2012,65(22):3763-3775
AbstractSynthesis and characterization of (E)-4-((5-bromo-2-(λ1-oxidanyl)benzylidene)amino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide (1), its substituted phthalonitrile derivative (2), and its tetra substituted zinc(II) phthalocyanine complex (3) were performed. Compounds 1, 2, and 3 were characterized by methods such as elemental analyses, FT-IR, 1H-NMR, 13C-NMR (except for 3), and MALDI-TOF mass spectra. The photophysical and photochemical properties of this substituted zinc(II) phthalocyanine complex aimed to be used as a photosensitizer were investigated in DMSO solution for determination of their photosensitizing abilities in photocatalytic applications such as photodynamic therapy (PDT). The influence of the substituent as a bioactive compound on the phthalocyanine skeleton on spectroscopic, photophysical, and photochemical properties were also determined and compared with unsubstituted zinc(II) phthalocyanine and some zinc(II) phthalocyanines containing different substituents previously studied. According to photophysical and photochemical investigations, 3 has potential as a photosensitizer for PDT. 相似文献
8.
Pinar Sen S. Zeki Yildiz Göknur Yasa Atmaca Ali Erdoğmuş 《Journal of Coordination Chemistry》2018,71(8):1258-1267
The content of this work is based on the introduction of the salicylhydrazone-zinc complexes into the phthalocyanine core. The reaction of the salicylhydrazone substituted ZnPc (1) with the related zinc(II) salt in basic conditions in DMF yielded bis[bis(salicyhydrazone)phenoxy)zinc(II)] phthalocyaninato zinc(II) (5) in which two salicylhydrazone-Zn complexes are linked through oxygen bridges to the macrocyclic core as three-nuclear complex. The novel compound synthesized in this study was fully characterized by general spectroscopic techniques such as FT-IR, UV-vis, 1H NMR, 13C NMR, elemental analysis and mass spectroscopy. In addition, spectral, photophysical (fluorescence quantum yields), and photochemical (generation of singlet oxygen and photo stability under light irradiation) properties of newly synthesized phthalocyanine (5) and the starting Pcs molecules used to obtain this molecule were investigated in DMSO solutions, comparatively. 相似文献
9.
Yi Ru Peng Kui Zhi Chen Jia Bao Wen Ji Cheng Shi Bao Quan Huang 《中国化学快报》2007,18(5):509-512
A novel anthraquinone phthalocyanine Al(Ⅲ) 4 and Co(Ⅱ) 5 were synthesized and characterized by elemental analysis, IR, UV/ vis, 1H NMR, HPLC and MS. The photophysical properties of the two metal complexes were studied and compared by ?uorescence spectrum method. 相似文献
10.
Asiye NasHalit Kantekin 《Polyhedron》2011,30(6):1085-1090
This paper describes a new symmetric metal-free phthalocyanine and its transition metal complexes which were prepared by a condensation of 1,2-dihydroacenaphthylen-1-ol 1 and 4-nitro phthalonitrile 2 with Co(II), Ni(II), Cu(II), and Zn(II) salts in 2-(dimethylamino)ethanol, respectively. The novel phthalocyanines bearing oxygen donor atoms on peripheral position have been characterized by IR, UV-Vis, 1H NMR, 13C NMR, Mass spectra and elemental analysis. The thermal behaviours of 4-8 were investigated by TG/DTA. 相似文献
11.
Su-Juan Pan Dong-Dong Ma Jian-Sheng Liu Kui-Zhi Chen Tian-Tian Zhang 《Journal of Coordination Chemistry》2016,69(4):618-627
A series of benzophenone chromospheres and zinc(II) phthalocyanine dichromophores labeled poly (aryl benzyl ether) dendrimer (Gn-DZnPc(BP)8n, n = 1?2) were synthesized. Their structures were characterized by elemental analysis, 1H NMR, IR, UV–vis and matrix-assisted laser desorption/ionization time-of-flight spectrometry (MALDI-TOF MS). Their photophysical properties were examined by steady-state and time-resolved fluorescence methods. Both the poly (aryl benzyl ether) dendrimer and BP terminal chromophores had a significant effect on photophysical properties of the zinc(II) phthalocyanine core. Time-resolved spectroscopic measurements indicated that the lifetime of benzophenone (donor) chromophore was longer than that of the zinc(II) phthalocyanine (acceptor). The fluorescence of the peripheral benzophenone chromophores was quenched by the phthalocyanine group attached to the focal point. All of these observations suggest that an intramolecular singlet energy transfer occurs in Gn-DZnPc(BP)8n molecules. The light-harvesting abilities of these molecules increased with generations due to an increase in the number of benzophenone chromophores. The energy transfer efficiencies were ca. 0.49 and 0.68 for generations 1 and 2, respectively, and the rate constants of the singlet-singlet energy transfer were ca. 108 s?1. The rate constants changed inconspicuously with increase of dendron generations. The intramolecular singlet-singlet energy transfer is proposed to proceed mainly via a Förster-type interaction mechanism involving the dendrimer backbone as a scaffold to hold the peripheral benzophenone chromophores and the phthalocyanine core together. This dendrimer was an effective new energy transmission complex with high efficiency and could be used as a potential light-harvesting system. 相似文献
12.
A macrocyclic diazadioxa dibromo compound was synthesized by ring closure of 1,2-bis-(2-iodoethoxy)-4,5-dibromo-benzene and 1,4-bis-(p-tolylsulfonyl)-ethylenediamine. Its phthalonitrile derivative was obtained by cyano substitution. This diazadioxa macrocyclic dibromo derivative was directly converted into the copper(II) phthalocyanine by reaction with CuCN in tetramethyl urea. Conversion of this phthalonitrile derivative into the metal-free phthalocyanine was accomplished by refluxing with DBU. The zinc(II) phthalocyanine was prepared by reaction of the dinitrile derivative with Zn(OAc)2 in quinoline. The lutetium bis-(phthalocyaninate) complex was obtained by treating the dinitrile derivative with anhydrous lutetium acetate and DBU in 1-hexanol. The new compounds were characterized by elemental analyses and IR, 1H NMR, mass, UV/Vis, and ESR spectra. 相似文献
13.
A tetranitrile monomer N,N-bis{2-[2-(3,4-dicyanophenoxy)ethoxy]ethyl}-4-methylbenzenesulfonamide (3) was synthesized by nucleophilic aromatic substitution of N,N-bis[2-(2-hydroxyethoxy)ethyl]-4-methylbenzenesulfonamide (1) onto 4-nitrophthalonitrile (2). The metal-free phthalocyanine polymer (4) was prepared by the reaction of a tetranitrile monomer 3 in 2-(dimethylamino)ethanol. Ni(II), Co(II) and Cu(II) phthalocyanine polymers were prepared by the reaction of the tetranitrile compound with the chlorides of Ni(II), Co(II) and Cu(II) in 2-(dimethylamino)ethanol (DMAE). The Zn(II)-phthalocyanine polymer was prepared by the reaction of the tetranitrile compound with the acetate of Zn(II) in DMAE. The new compounds were characterized by a combination of IR, 1H NMR, 13C NMR, UV–Vis, elemental analysis and MS spectral data. 相似文献
14.
4-[2-(Phenylthio)ethoxy]phthalonitrile 3 was synthesized by nucleophilic displacement of nitro group in 4-nitrophthalonitrile with 2-(phenylthio)ethanol 1. The metal-free phthalocyanine 4 was prepared by the reaction of a dinitrile monomer with 2-(dimethylamino)ethanol. Ni(II), Co(II), Cu(I) phthalocyanines 5, 7, 8 were prepared by reaction of the dinitrile compound with the chlorides of Ni(II), Co(II), Cu(I) in DMAE. Zn(II) phthalocyanine 6, was prepared by reaction of the dinitrile compound with the acetates of Zn(II) in DMAE. Electrochemical behaviours of novel metal-free, Co(II) and Zn(II) phthalocyanines were investigated by cyclic voltammetry, potential differential pulse voltammetry techniques. The new compounds were characterized by a combination of IR, 1H NMR, 13C NMR, UV–Vis, elemental analysis and MS spectral data. 相似文献
15.
Summary. A macrocyclic diazadioxa dibromo compound was synthesized by ring closure of 1,2-bis-(2-iodoethoxy)-4,5-dibromo-benzene and 1,4-bis-(p-tolylsulfonyl)-ethylenediamine. Its phthalonitrile derivative was obtained by cyano substitution. This diazadioxa macrocyclic
dibromo derivative was directly converted into the copper(II) phthalocyanine by reaction with CuCN in tetramethyl urea. Conversion
of this phthalonitrile derivative into the metal-free phthalocyanine was accomplished by refluxing with DBU. The zinc(II) phthalocyanine was prepared by reaction of the dinitrile derivative with Zn(OAc)2 in quinoline. The lutetium bis-(phthalocyaninate) complex was obtained by treating the dinitrile derivative with anhydrous lutetium acetate and DBU in 1-hexanol. The new compounds were characterized by elemental analyses and IR, 1H NMR, mass, UV/Vis, and ESR spectra.
Received May 8, 2001. Accepted (revised) June 25, 2001 相似文献
16.
In this study, we report a new ligand, 6-hexyloxy-3-[p-(3′,4′-dicyanophenoxy)phenyl]coumarin, and its fluorescent tetrasubstituted phthalocyanines {M[Pc(OBzCou)4], M = 2H, Zn(II), Co(II); Bz: Benzene}. The effect of the coumarin derivative on the intensity of the fluorescence spectra of the metal-free (H2Pc) and zinc phthalocyanine (ZnPc) derivatives was investigated. The change of the emission properties of both the coumarin moieties and the phthalocyanine core in the presence of the metal ion and the ring-opening reaction of the coumarin were studied by means of steady-state fluorescence spectroscopy. The radiative decay of the Pcs and the treated coumarin substituents bound to the Pcs was examined. The novel chromogenic compounds were characterized by elemental analysis, 1H NMR, 13C NMR, Maldi-TOF, IR and UV–Vis spectral data. The photophysical properties of the Pcs are extensively affected by their state of aggregation: in particular, dimerization and aggregation result in a remarkable modification of the absorption and emission bands and may induce significant quenching of the usually strong Pc fluorescence. The electronic spectra exhibit a band of coumarin identity together with characteristic Q and B bands of the phthalocyanine core. 相似文献
17.
Zhigang Xue Rinaldo Poli 《Journal of polymer science. Part A, Polymer chemistry》2013,51(16):3494-3504
The radical polymerization of vinyl acetate (VAc) is moderated by iron(II) acetylacetonate (Fe(acac)2) by the organometallic route (OMRP), as well as by degenerative transfer polymerization (DTP) when in the presence of excess radicals, through the formation of thermally labile organometallic FeIII dormant species. The poly(vinyl acetate) (PVAc)‐FeIII(acac)2 dormant species has been isolated in the form of an oligomer and characterized by 1H NMR, EPR, and IR methods, and then used as a single‐component initiator for the OMRP of VAc. The degree of polymerization of this isolated oligomeric species demonstrates the limited ability of Fe(acac)2, relative to the Co(acac)2 congener, to rapidly trap the growing PVAc radical chain. Control under OMRP conditions is improved by the presence of Lewis bases, especially PMe2Ph. On the other hand, iron(II) phthalocyanine inhibits the radical polymerization of VAc completely. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013 , 51, 3494–3504 相似文献
18.
Leszek Pazderski Tomasz Pawlak Jerzy Sitkowski Lech Kozerski Edward Szłyk 《Magnetic resonance in chemistry : MRC》2010,48(6):450-457
1H, 13C and 15N NMR studies of iron(II), ruthenium(II) and osmium(II) tris‐chelated cationic complexes with 2,2′‐bipyridine and 1,10‐phenanthroline of the general formula [M(LL)3]2+ (M = Fe, Ru, Os; LL = bpy, phen) were performed. Inconsistent literature 1H signal assignments were corrected. Significant shielding of nitrogen‐adjacent protons [H(6) in bpy, H(2) in phen] and metal‐bonded nitrogens was observed, being enhanced in the series Ru(II) → Os(II) → Fe(II) for 1H, Fe(II) → Ru(II) → Os(II) for 15N and bpy → phen for both nuclei. The carbons are deshielded, the effect increasing in the order Ru(II) → Os(II) → Fe(II). Copyright © 2010 John Wiley & Sons, Ltd. 相似文献
19.
Meryem Çamur 《Journal of organometallic chemistry》2010,695(1):45-227
The phthalonitrile derivative chosen for the synthesis of substituted phthalocyanines [M: 2H, Zn(II), Co(II)] with four chloro and four phenyloxyacetic acid substituents on the periphery is 4-chloro-5-(4-phenyloxyacetic acid)phthalonitrile. The sodium salt of carboxyl substituted zinc phthalocyanine is good soluble in water. Further reactions of zinc and cobalt phthalocyanines bearing phenyloxyacetic acid with thionylchloride gave the corresponding acylchlorides. This functional group reacted with hydroxymethylferrocene in dry DMF to obtain ferrocenyl substituted phthalocyanines. Also chloro substituent in new phthalonitrile was substituted with hexylsulfanyl substituent and its cyclotetramerization in the presence of Zn(AcO)2·2H2O and 2-(dimethylamino)ethanol resulted with zinc phthalocyanine. The compounds have been characterized by elemental analysis, MALDI-TOF mass, FT-IR, 1H NMR, UV-Vis and fluorescence data. Aggregations properties of phthalocyanines were investigated at different concentrations in tetrahydrofuran, dimethylformamide, dimethylsulfoxide, water, and water/ethanol mixture. Also fluorescence spectral properties are reported. 相似文献
20.
《Journal of Coordination Chemistry》2012,65(18):1965-1972
New metal-free phthalocyanine (7) fused symmetrically in peripheral positions with four dithiatetraoxa macrocycles, has been synthesized by cyclotetramerization of the isoindolinediimine derivative of macrocyclic 6. Metallophthalocyanine (8) was synthesized by reaction of phthalonitrile derivative (5) with anhydrous nickel(II) chloride. The new compounds were characterized by elemental analysis, 1H and 13C-NMR, IR UV–Vis and mass spectroscopies. 相似文献