Substituted Phthalocyanine Derivatives Research Articles

Fluorocarbon Substituted Peripherally and Non-Peripherally Tetra Phthalocyanine Compounds: Synthesis, Characterization and Aggregation Properties

This work presents a series of novel peripherally and non-peripherally tetra substituted phthalocyanine derivatives containing 4-[(4,4,5,5,5-pentafluoropentyl)oxy groups. Firstly, phthalonitrile derivatives (2 and 3) were synthesized. These phthalonitrile derivatives were used synthesis of peripherally tetra substituted (metal-free 4, manganese(III) 5, nickel(II) 6 and cobalt(II) 7) phthalocyanines and non-peripherally tetra substituted (magnesium(II) 8, zinc(II) 9, nickel(II) 10 and cobalt(II) 11) functionalized with the fluorocarbon compound “4,4,5,5,5-pentafluoro-1-pentanol”. Synthesized novel compounds have been characterized by combination of the FT-IR, 1H NMR/ 13C NMR, MALDI-TOF-MS and UV-Vis spectroscopy (for phthalocyanines). In the last part of the study, the effect of the solvent on the aggregation behavior of the metallophthalocyanines NiPc (6 and 10) and CoPc (7 and 11) was studied using different solvents (THF, DMF, DMSO etc). In addition, the aggregation behavior of NiPcs and CoPcs was investigated at different concentrations ranging from 2 x 10-6 to 12 x 10-6 M in CHCl3.

A Hybrid Nanomaterial Based on Single Walled Carbon Nanotubes Cross-Linked via Axially Substituted Silicon (IV) Phthalocyanine for Chemiresistive Sensors.

In this work, the novel hybrid nanomaterial SWCNT/SiPc made of single walled carbon nanotubes (SWCNT) cross-linked via axially substituted silicon (IV) phthalocyanine (SiPc) was studied as the active layer of chemiresistive layers for the detection of ammonia and hydrogen. SWCNT/SiPc is the first example of a carbon-based nanomaterial in which an axially substituted phthalocyanine derivative is used as a linker. The prepared hybrid material was characterized by spectroscopic methods, thermogravimetry, scanning and transmission electron microscopies. The layers of the prepared hybrid were tested as sensors toward ammonia and hydrogen by a chemiresistive method at different temperatures and relative humidity as well as in the presence of interfering gases like carbon dioxide, hydrogen sulfide and volatile organic vapors. The hybrid layers exhibited the completely reversible sensor response to both gases at room temperature; the recovery time was 100–200 s for NH3 and 50–120 s in the case of H2 depending on the gas concentrations. At the relative humidity (RH) of 20%, the sensor response was almost the same as that measured at RH 5%, whereas the further increase of RH led to its 2–3 fold decrease. It was demonstrated that the SWCNT/SiPc layers can be successfully used for the detection of both NH3 and H2 in the presence of CO2. On the contrary, H2S was found to be an interfering gas for the NH3 detection.

G-quadruplex and calf thymus DNA interaction of quaternized tetra and octa pyridyloxy substituted indium (III) phthalocyanines

The interactions of small molecules with G-quadruplex and double stranded DNA are important due to their potential biological and medical usages. In the present paper, the interactions of indium (III) phthalocyanines (quaternized 2,3,9,10,16,17,23,24-octakis-[(3-pyridyloxy) phthalocyaninato] chloroindium(III): OInPc and quaternized 2(3),9(10),16(17),23(24)-tetrakis-[(3-pyridyloxy) phthalocyaninato] chloroindium(III): TInPc) with hybrid G-quadruplex (Tel 21) and parallel G-quadruplexes (nucleolin, KRAS, c-MYC, vegf) were studied. The interactions of these phthalocyanines with ctDNA were also investigated. These interactions were measured by different spectroscopic techniques such as UV–Vis, fluorescence and circular dichroism. The UV–Vis spectroscopic data treated with Benesi-Hildebrand equation and Benesi-Hildebrand constants (KBH) were calculated. These constants were found higher for octa peripheral pyridyloxy substituted phthalocyanine, OInPc. Besides, UV–Vis analysis showed that the interaction of G-quadruplexes with tetra peripheral pyridyloxy substituted phthalocyanine derivative (TInPc) resulted in removal of central indium (III) atom from the cavity of phthalocyanine macrocycle. The UV–Vis melting studies as well as fluorescence replacement techniques were also employed for clarification of mechanism. The binding mode of molecules with ct DNA was also supported with viscosity measurements. From the results, the stabilization and destabilization of G-quadruplex depending on the concentration of the OInPc and TInPc showed that these two indium (III) phthalocyanines have the potential of both the elucidation role of G-quadruplexes in gene expression and the usage in cancer therapy.

Microwave-assisted synthesis of novel nonperipherally substituted metallophthalocyanines bearing (7-(trifluoromethyl)quinolin-4-yl)oxy groups

The synthesis, characterization, and spectroscopic properties of novel nonperipherally tetrasubstituted metallophthalocyanines (zinc, cobalt, copper, manganese, and indium) bearing 4 (7-(trifluoromethyl)quinolin-4-yl)oxy units has been reported. The new compounds have been characterized using UV-Vis, IR, 1H NMR, 13C NMR, 19F NMR, and mass spectroscopic data. The absorption properties of these new complexes were compared to those of peripherally substituted phthalocyanine derivatives. Based on the structural, spectroscopic, and absorption studies, it was found that the substitution effect altered the electronic structures significantly. The results provide useful information to understand the effect of peripheral or nonperipheral substitution on the properties of this macrocyclic ring. Photophysical properties with zinc(II) phthalocyanine were found, including electronic absorption and fluorescence quantum yield. The fluorescence of the complex was investigated in DMF and it was found that benzoquinone was an effective quencher.

Liquid crystalline alkylthia-substituted novel phthalocyanines: synthesis and characterization

Methylene-bridged tetra- and octa-alkylthia substituted metal free- and Ni ( II ) phthalocyanines were synthesized from the corresponding phthalonitrile derivatives in the presence of the anhydrous metal salt ( NiCl 2) or a strong organic base. The new compounds were fully characterized by elemental analyses, UV-vis, IR, NMR and mass spectra. The mesogenic properties of these materials were studied by differential scanning calorimetry, optical microscopy and X-ray diffraction investigations. X-ray diffraction patterns of the mesophase confirmed that the tetra- and the octa-substituted compounds formed hexagonal columnar mesophases (Colh). The mesogenic properties of these compounds were compared to that of their octa alkythia substituted phthalocyanine derivatives in the literature.

ChemInform Abstract: Routes to Some 3,6‐Disubstituted Phthalonitriles and Examples of Phthalocyanines Derived Therefrom: An Overview

The paper reviews a selection of synthetic pathways that provide access to 3,6-disubstituted phthalonitriles, precursors for the synthesis of 1,4,8,11,15,18,22,25-octasubstituted phthalocyanine derivatives. Early routes using Diels–Alder reactions for the synthesis of 3,6-dialkyl, 3,6-dialkoxymethyl, 3,6-dialkenyl and 3,6-diphenylphthalonitriles are appraised. However, the emphasis of the review focuses on the scope and applications of 2,3-dicyanohydroquinone as a starting material for obtaining 3,6-disubstituted phthalonitriles. The earliest example of the use of 2,3-dicyanohydroquinone concerned its O-alkylation to afford 3,6-dialkoxyphthalonitriles. These are immediate precursors to near-infrared absorbing phthalocyanine derivatives. Triflation of 2,3-dicyanohydroquinone extends the scope of the compound for phthalocyanine synthesis; the bis-triflate derivative is susceptible to SNAr reactions and readily reacts with thiols to provide 3,6-bis(alkylsulfanyl) and 3,6-bis(arylsulfanyl)phthalonitriles. 3,6-Bis(phenylselenyl)phthalonitrile has also been obtained recently from the same precursor. Phthalocyanine derivatives obtained from them typically show a strongly bathochromically shifted Q-band absorption that is particularly sensitive to the central metal ion. The bis-triflate of 2,3-dicyanohydroquinone is also an ideal precursor for participation in cross-coupling reactions. Examples from the University of East Anglia group and elsewhere are presented which show the application of the nickel-catalyzed Negishi coupling reaction using alkylzinc halide derivatives. Yields of 3,6-dialkylphthalonitriles and 3,6-bis(substituted alkyl)phthalonitriles range from ca. 40 to 70%. Direct comparison for one example shows that the yield from the Negishi coupling method is higher than that using the Suzuki coupling protocol. Examples of the preparation of 3,6-diarylphthalonitriles from 2,3-dicyanohydroquinone bis-triflate using the Suzuki coupling reaction are reported with yields of the order of 65–70%. The review also includes a further application of 2,3-dicyanohydroquinone as a precursor to both monobromo and dibromo derivatives of 3,6-dibutoxyphthalonitrile. These compounds provide opportunities for cross-coupling at the brominated sites to provide more complex derivatives with the potential to serve as precursors of highly substituted phthalocyanine derivatives.

SYNTHESIS AND CHARACTERIZATION OF SOME (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-HEPTADECAFLUORODECYL) (METHYL) SULFANE SUBSTITUTED TITANIUM PHTHALOCYANINE DERIVATIVES

Symmetrically substituted phthalocyanine derivatives have been synthesized from the reaction of anhydrous metal salts of titanium with 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthio) phthalonitrile ( 3) . 4-phthalonitrile ( 1) and 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthiol) ( 2) in dry dimethylformamide as solvent and using K 2 CO 3 as base via the common method of nucleophilic substitution of an activated nitro group in an aromatic ring. The compound 3,9,17,23-bis[ethane-1,1- p- phenol-2,2- p- phenokxy]phthalocyaninatocobalt (II) (FlTi 2 CoPc) ( 4) was reacted with the compound 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthio) phthalocyaninatotinanium (IV) ( 5) , which is similar to those synthesized in the past, to syhthesize a new derivative containing three phthalocyanines 3,9,17,23-bis[ethane-1,1- p -(4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthio) phthalocyaninatotinanium (IV))-2,2- p- phenokxy]phthalocyaninatocobalt (II) (FlTi 2 CoPc) ( 6) . The synthesized molecules have been characterized by 19 F NMR, HETCOR, MALDI-TOFF, UV-Vis and IR spectroscopies.

Routes to some 3,6-disubstituted phthalonitriles and examples of phthalocyanines derived therefrom: An overview

The paper reviews a selection of synthetic pathways that provide access to 3,6-disubstituted phthalonitriles, precursors for the synthesis of 1,4,8,11,15,18,22,25-octasubstituted phthalocyanine derivatives. Early routes using Diels–Alder reactions for the synthesis of 3,6-dialkyl, 3,6-dialkoxymethyl, 3,6-dialkenyl and 3,6-diphenylphthalonitriles are appraised. However, the emphasis of the review focuses on the scope and applications of 2,3-dicyanohydroquinone as a starting material for obtaining 3,6-disubstituted phthalonitriles. The earliest example of the use of 2,3-dicyanohydroquinone concerned its O -alkylation to afford 3,6-dialkoxyphthalonitriles. These are immediate precursors to near-infrared absorbing phthalocyanine derivatives. Triflation of 2,3-dicyanohydroquinone extends the scope of the compound for phthalocyanine synthesis; the bis-triflate derivative is susceptible to S N Ar reactions and readily reacts with thiols to provide 3,6-bis(alkylsulfanyl) and 3,6-bis(arylsulfanyl)phthalonitriles. 3,6-Bis(phenylselenyl)phthalonitrile has also been obtained recently from the same precursor. Phthalocyanine derivatives obtained from them typically show a strongly bathochromically shifted Q-band absorption that is particularly sensitive to the central metal ion. The bis-triflate of 2,3-dicyanohydroquinone is also an ideal precursor for participation in cross-coupling reactions. Examples from the University of East Anglia group and elsewhere are presented which show the application of the nickel-catalyzed Negishi coupling reaction using alkylzinc halide derivatives. Yields of 3,6-dialkylphthalonitriles and 3,6-bis(substituted alkyl)phthalonitriles range from ca. 40 to 70%. Direct comparison for one example shows that the yield from the Negishi coupling method is higher than that using the Suzuki coupling protocol. Examples of the preparation of 3,6-diarylphthalonitriles from 2,3-dicyanohydroquinone bis-triflate using the Suzuki coupling reaction are reported with yields of the order of 65–70%. The review also includes a further application of 2,3-dicyanohydroquinone as a precursor to both monobromo and dibromo derivatives of 3,6-dibutoxyphthalonitrile. These compounds provide opportunities for cross-coupling at the brominated sites to provide more complex derivatives with the potential to serve as precursors of highly substituted phthalocyanine derivatives.

New water soluble phenoxy phenyl diazenyl benzoic acid substituted phthalocyanine derivatives: Synthesis, antioxidant activities, atypical aggregation behavior and electronic properties

Novel substituted phthalonitrile derivatives were obtained by the reaction of 2-(4-hydroxyphenylazo)benzoic acid and 4,5-dichloro-1,2-dicyanobenzene, or 4-nitrophthalonitrile. Peripherally phenoxy phenyl diazenyl benzoic acid substituted zinc (II) phthalocyanine complexes, and their sodium salts were synthesized and characterized for the first time. The newly synthesized phthalocyanine complexes show excellent solubility in water. The aggregation investigations carried out in different concentrations indicate that phenoxy phenyl diazenyl benzoic acid-substituted phthalocyanine compounds do not have any aggregation behavior for the concentration range of 7.00 × 10−5–4.38 × 10−6 M in DMF. The antioxidant activities of DMF solution of compounds were analyzed through radical scavenging, and chelating ability to Fe2+ cation. Additionally, new compounds did not show any antibacterial activity against some selected bacteria cultures. Moreover, the ground-state geometries of the complexes were optimized using density functional theory (DFT) methods at B3LYP/6-31G(d,p) level in order to obtain information about the 3D geometries and electronic structure.

Synthesis, characterization, photophysical and photochemical properties of tetra-2-[2-(benzothiazolylthio)]ethoxy substituted phthalocyanine derivatives

The metal-free and zinc (II) phthalocyanine compounds tetra substituted with 2-(2-benzothiazolylthio)ethoxy groups have been synthesized for the first time in this study for comparison central metal effect on photophysical and photochemical properties. The new compounds have been characterized by IR, 1H NMR, 13C NMR and MS spectra data. These compounds showed excellent solubility in most common organic solvents. The photophysical and photochemical properties of metal-free and zinc (II) phthalocyanine compounds have been studied in DMF and toluene in order to investigate of polar and non-polar solvent effect on these properties. The fluorescence quenching behaviour of the studied compounds by 1,4-benzoquinone (BQ) have also been studied in DMF and toluene.

Tetra and octa(2,6-di-iso-propylphenoxy)-substituted phthalocyanines: a comparative study among their photophysicochemical properties

This work reports on the synthesis of novel metal free, zinc, aluminum, gallium and indium tetra and octa (2,6-di-iso-propylphenoxy)-substituted phthalocyanine derivatives. UV-visible and 1H NMR analyses confirm that a non-planar conformation, adapted by the phenoxy substituents due to steric interaction in both derivative series, perfectly discourage cofacial aggregation. Fluorescence quantum yields vary as a function of the number of substituents on the ring periphery, while the fluorescence lifetimes display no distinct trend. Triplet quantum yields are significantly larger for the tetra 2,6-di-iso-propylphenoxy- substituted derivatives relative to their corresponding octa-substituted species. However there was no overall trend in the triplet lifetime values. For almost all of the phthalocyanine derivatives, singlet oxygen was produced with relatively good quantum yields. This study explores the possibility of fine-tuning their physicochemical properties by simple structural modification.

The determination of the photosensitizing properties of mercapto substituted phthalocyanine derivatives in the presence of quantum dots capped with mercaptopropionic acid

This work reports on the synthesis of several novel water soluble metallophthalocyanines containing Zn2+, In3+, Ga3+ or Si4+ as central metal ions and tetra substituted with mercaptoacetic acid and mercaptopropionic acid. The complexes were characterized using infra red, nuclear magnetic resonance and mass spectroscopies as well as elemental analysis. All the complexes are water soluble but the majority are highly aggregated in water and organic solvents. The complex containing Zn as a central metal and mercaptopropionic acid as a substituent was not aggregated allowing for the determination of photophysical parameters. This complex had triplet state quantum yield of 0.61 in DMF and 0.88 in DMSO while the fluorescence quantum yield was 0.13 in DMSO. The determination of photophysical properties of the complex containing Zn as a central metal and mercaptopropionic acid were carried out in the presence of mercaptopropionic acid capped CdTe quantum dots. There is an increase in triplet state quantum yield from 0.88 (for the phthalocyanine alone) to 0.94 (in the presence of CdTe quantum dots) in DMSO.

Nonperipherally Octa(butyloxy)‐Substituted Phthalocyanine Derivatives with Good Crystallinity: Effects of Metal–Ligand Coordination on the Molecular Structure, Internal Structure, and Dimensions of Self‐Assembled Nanostructures

To investigate the effects of metal-ligand coordination on the molecular structure, internal structure, dimensions, and morphology of self-assembled nanostructures, two nonperipherally octa(alkoxyl)-substituted phthalocyanine compounds with good crystallinity, namely, metal-free 1,4,8,11,15,18,22,25-octa(butyloxy)phthalocyanine H(2)Pc(alpha-OC(4)H(9))(8) (1) and its lead complex Pb[Pc(alpha-OC(4)H(9))(8)] (2), were synthesized. Single-crystal X-ray diffraction analysis revealed the distorted molecular structure of metal-free phthalocyanine with a saddle conformation. In the crystal of 2, two monomeric molecules are linked by coordination of the Pb atom of one molecule with an aza-nitrogen atom and its two neighboring oxygen atoms from the butyloxy substituents of another molecule, thereby forming a Pb-connected pseudo-double-decker supramolecular structure with a domed conformation for the phthalocyanine ligand. The self-assembling properties of 1 and 2 in the absence and presence of sodium ions were comparatively investigated by scanning electronic microscopy (SEM), spectroscopy, and X-ray diffraction techniques. Intermolecular pi-pi interactions between metal-free phthalocyanine molecules led to the formation of nanoribbons several micrometers in length and with an average width of approximately 100 nm, whereas the phthalocyaninato lead complex self-assembles into nanostructures also with the ribbon morphology and micrometer length but with a different average width of approximately 150 nm depending on the pi-pi interactions between neighboring Pb-connected pseudo-double-decker building blocks. This revealed the effect of the molecular structure (conformation) associated with metal-ligand (Pb-N(isoindole), Pb-N(aza), and Pb-O(butyloxy)) coordination on the dimensions of the nanostructures. In the presence of Na(+), additional metal-ligand (Na-N(aza) and Na-O(butyloxy)) coordination bonds formed between sodium atoms and aza-nitrogen atoms and the neighboring butyloxy oxygen atoms of two metal-free phthalocyanine molecules cooperate with the intrinsic intermolecular pi-pi interactions, thereby resulting in an Na-connected pseudo-double-decker building block with a twisted structure for the phthalocyanine ligand, which self-assembles into twisted nanoribbons with an average width of approximately 50 nm depending on the intertetrapyrrole pi-pi interaction. This is evidenced by the X-ray diffraction analysis results for the resulting aggregates. Twisted nanoribbons with an average width of approximately 100 nm were also formed from the lead coordination compound 2 in the presence of Na(+) with a Pb-connected pseudo-double-decker as the building block due to the formation of metal-ligand (Na-N(aza) and Na-O(butyloxy)) coordination bonds between additionally introduced sodium ions and two phthalocyanine ligands of neighboring pseudo-double-decker building blocks.

Negative differential resistance effects in spun films of substituted phthalocyanine derivatives

Spun films of novel substituted lead phthalocyanine derivatives between aluminum and indium tin oxide electrodes exhibit large, reproducible negative differential resistance (NDR) in their current–voltage characteristics and can be electrically switched between a high conductance on state and a low conductance off state. Space charge limited conduction mechanism was identified from temperature dependent measurements to be responsible for charge transport. The NDR effect may be due to the charge storage in the structure near the electrodes.

Synthesis, characterizations and biological studies of symmetrically substituted 2, 9, 16, 23-tetra-hydroxyphenylimino phthalocyanine complexes

The recent paper describes the synthesis and characterization of metal (II) 2, 9, 16, 23-tetra-hydroxyphenylimino phthalocyanines (M–OHPhImPc) of Co (II), Cu (II), Ni (II), and Zn (II). The dark bluish green colored tetramino substituted phthalocyanine derivatives are characterized by the various physico-chemical techniques such as elemental analysis, magnetic susceptibility, UV-Visible, IR, powder X-ray diffraction, and thermogravimetric analysis to check the structural integrity, purity, and thermal stability. The variations of magnetic moment as a function of field strength indicated the presence of intermolecular co-operative interactions. The above said compounds were screened for their antibacterial and antifungal activities.

Synthesis, spectral, magnetic, thermal and antibacterial studies on symmetrically substituted 1,8,15,22-tetra- phenylpropene-1-imino phthalocyanines

This article describes a simple method developed for the synthesis of symmetrically substituted 1,8,15,22-tetra-phenylpropene-1-imino phthalocyanines (M-PhproImPcs) of cobalt(II), copper(II), nickel(II) and zinc(II) by condensing 1,8,15,22-tetra amino phthalocyanines with cinnamaldehyde. The dark bluish-green colored tetraimino substituted phthalocyanine derivatives were characterized by elemental analysis, electronic spectra, IR spectra, magnetic susceptibility, powder XRD and thermogravimetric analysis (TGA) to check the structural integrity and purity. The variations of magnetic moment as a function of field strength indicated the presence of intermolecular co-operative interactions. The complexes were also evaluated for their antibacterial activities.

Prediction, synthesis and investigation of mesomorphism of new octa(benzo-15-crown-5)-substituted derivatives of phthalocyanine and its metallo complexes [Zn(II), Ni(II)

First calculation of molecular parameters (MP) of new octa-(benzo-15-crown-5)-substituted phthalocyanine derivatives and of its metallo complexes Zn(II), Ni(II) (Ib, Ic) is carried out. A prediction was made of the possible formation therefrom of metaphases, and for that purpose the synthesis of these compounds and investigation of their mesomorphic properties was performed. For compounds Ia-Ic the formation of high-temperature enantiotropic mesophases was established typical for discotic mesogenes, in good agreement with the prediction. Proceeding from the data on miscibility of 2,3,9,10,16,17,23,24-octa-[(4′-benzo-15-crown-5)-oxy]-phthalocyanine Ia with discotic mesogene 2,3,6,7,10,11-hexa(cyclohexanebenzoyloxy)triphenylene (II) displaying nematic mesomorphism the compound Ia was assigned to the group of nematic mesogenes and by the texture of the mixture to discotic mesogenes forming columnar type nematic phase (NCol). Convergence of the results of prediction and experimental data is about 83%.

Synthesis, structural investigations and biological studies on symmetrically substituted 3,3′,3",3"′-tetra-methoxyphenylimino phthalocyanine complexes

The present paper describes the synthesis and characterization of novel metal (II) 3,3′,3″,3‴-tetramethoxyphenylimino substituted phthalocyanines (M-MeOPhImPcs) of copper (II), cobalt (II), nickel (II) and zinc (II) by condensing the 3,3′,3″,3″′-tetra amino phthalocyanines with anisaldehyde. The dark bluish green colored tetraimino substituted phthalocyanine derivatives were characterized by various physico-chemical techniques like elemental analysis, magnetic susceptibility, electronic, IR, powder X-ray diffraction and thermo gravimetric analysis (TGA) to check the structural integrity and purity. The variations of magnetic moment as a function of field strength indicated the presence of inter molecular co-operative interactions. The complexes were also evaluated for their antifungal and antibacterial activities.

Synthesis and characterization of liquid crystalline unsymmetrically substituted phthalocyanines

The synthesis of unsymmetrically substituted phthalocyanines bearing two p-tolyl-sulfonyl (tosyl)amido and six alkylthio moieties was achieved by cyclotetramerisation of two different phthalonitrile derivatives, namely 1,2-di(alkylthio)-4,5-dicyanobenzene and 4,5-dicyano- N, N′-ditosyl- o-phenylenediamine in the presence of an anhydrous metal salt and strong base. The new compounds were characterized by elemental analyses, UV/Vis, IR, NMR and mass spectra. The mesogenic properties of these new materials were studied by differential scanning calorimetry (DSC) and polarizing optical microscopy. The mesogenic properties of these compounds were compared to that of their symmetric analogous, octaalkythia substituted phthalocyanine derivatives.

Synthesis, structural investigations and biological studies on symmetrically substituted 4,4′,4″,4″′- tetra-methoxyphenylimino phthalocyanine complexes

The synthesis and characterization of novel metal(II) 4,4′,4″,4″′-tetra-methoxyphenylimino substituted phthalocyanines (MImPc) of copper(II), cobalt(II), nickel(II) and zinc(II) by condensing the 4,4′,4″,4″′-tetra amino phthalocyanines with anisaldehyde are described. The dark bluish green colored tetraimino substituted phthalocyanine derivatives are characterized by various physico-chemical techniques, elemental analysis, magnetic susceptibility, electronic, and IR spectra, powder X-ray diffraction and thermo gravimetric analysis (TGA) to check the structural integrity and purity. The variations of magnetic moment as a function of field strength indicated the presence of intermolecular co-operative interactions. The complexes are also evaluated for their antifungal and antibacterial activities.