CONTENTS

voltammetric, spectroelectrochemical, and electrocatalytic properties of the metallophthalocyanines bearing four chloro and four biphenyl-malonic ester bulky groups (MPc; M = Cu^II, Zn^II, Pb^II and Co^II) were investigated. CoPc has significant catalytic activities towards hydrogen evolution reaction. The catalytic activity of the complex enhanced significantly, when the complex was incorporated into the cation exchange Nafion polymeric matrix.

Novel peripherally 2-mercaptopyridine tetrasubstituted zinc phthalocyanine and its quaternized derivative were synthesized. The quaternized compound shows excellent solubility in water, which makes it a potential photosensitizer for use in photodynamic therapy (PDT) of cancer. Cytotoxicity of PDT on two pleural malign mesothelioma cell lines was determined by colorimetric proliferation assay.

The synthesis of metal-free (3) and metallophthalocyanines [M = Zn (4), Co (5)] obtained from 7,8-dihexyloxy-3-[p-(3',4'-dicyanophenoxy)phenyl]coumarin (2) are described. The newly prepared compounds have been characterized by elemental analysis, IR, NMR, mass and UV-vis spectral data. Their electronic absorption and fluorescence spectral properties are reported. Cyclic voltammetry of the compounds have also been studied.

Tetraimidazophthalocyanines (ImiPc(M)) have been synthesized and the effect of the four imidazoles ring introduced were compared and discussed. The synthesis of novel 2-substituted-5,6-dicyanobenzimidazoles precursor was performed in one-pot or two-step pathway using microwave irradiation. Especially the Rosenmund-Von Braun reactions, in these conditions, occurred with good yields.

In this study, we report a novel both alcohol and haloganated solvent soluble selective ionophore functional ligand and its β-substituted 2(3),9(10),16(17),23(24)-tetrakis(1-hydroxyhexan-3-ylthio)-phthalocyanines, M{Pc[S-CH(CH₂CH₂CH₃)(CH₂CH₂OH)]₄}, (Pc: Phthalocyanine) (M = Zn, Cu, Co), where -OH indicates peripheral functionality.

Ni(II) and Zn(II) phthalocyanines carrying four or eight branched oligo(ethyleneoxy)thia groups on peripheral positions have been synthesized from new phthalonitrile derivatives. Preliminary investigation of the photophysical and photochemical properties of phthalocyanine complexes are very useful for further PDT applications. On the other hand, the mesogenic properties of these new materials were studied by differential scanning calorimetry (DSC), optical polarized microscopy and X-ray investigations.

A novel synthetic pathway for the preparation of a new phthalonitrile derivative, methyl (E)-3-[2-(3,4-dicyanophenoxy)-4-(hexyloxy)phenyl]acrylate, based on the opening of the lactone ring of 7-hexyloxycoumarin (2H-1-benzopyrane-2-one, 2H-chromen-2-one) and ether formation of the formed hydroxy group with 4-nitrophthalonitrile, is presented. Cyclotetramerization of this dinitrile in 2-N,N-dimethylaminoethanol gives the desired Zn(II), Co(II) and Cu(II) phthalocyanines with four methyl 4-hexyloxy-2-phenoxy acrylate moiety on periphery. The complexes are characterized by IR, elemental analysis, ¹H NMR, ¹³C NMR , MALDI-TOF and UV-vis spectroscopy. The redox behavior of the complexes are also discussed.

The synthesis of the iron phthalocyanine bearing four fused tetraazamacrocycles starting from N,N',N″,N‴-tetrakis(p-tolylsulfonyl)triethylenetetraamine and 1,2-dibromo-4,5-bis(bromomethyl)benzene is reported. Its efficiency as oxidation catalyst was tested for the practically important oxidation of 2,3,6-trimethylphenol (TMP) at different reaction conditions.

Metal-free and metallophthalocyanines with four 9-anthroyl groups bound through ethylthio ester bridges on the periphery have been prepared. The energy transfer to the phthalocyanine core and radiative decays of the 9-anthroyl emission and phthalocyanine core were examined.

A complete series of solketal octasubstituted phthalocyanines have been synthesized, with peripheral (β) or non-peripheral (α) substitution pattern. Their ¹³C NMR and UV-vis properties are compared relatively to this substitution pattern or the nature of the central metal (Ni, Zn or H₂).

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