A new hexadeca substituted non-aggregating zinc phthalocyanine

Atsay, Armağan; Gül, Ahmet; Koçak, Makbule Burkut

doi:10.1016/j.dyepig.2013.09.012

Cited by 36 publications

(23 citation statements)

References 25 publications

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“…Aggregation in MPc's is dependent on the concentration, temperature, the nature of metal ions, solvent and the substituents [20,22,42]. Aggregation behaviours of 2-5 were examined by UV-vis spectroscopy at different concentrations in THF.…”

Section: Ground State Electronic Absorption and Aggregation Behaviourmentioning

confidence: 99%

“…Spectroscopic properties of the phthalocyanines also depend on the positions of the substituents. When electron-donating substituents are bound to nonperipheral positions of the phthalocyanine skeleton the Q-band shifts further to longer wavelength than substitution at peripheral position [19][20][21][22]. It is well known that having an axial substituent on the metal center of the phthalocyanine also displays a bathochromic shift of the Q-band absorption maxima [23].…”

Section: Introductionmentioning

confidence: 96%

“…Recently, our group concentrated on synthesizing and understanding the properties of hexadecasubstituted phthalocyanines [20,30,31]. Naphthalene is a wellknown fluorescent substituent, frequently used as a luminophore in supramolecular systems.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, electrochemistry and in situ spectroelectrochemistry of novel hexadeca-substituted phthalocyanines with three different groups

et al. 2015

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Section: Ground State Electronic Absorption and Aggregation Behaviourmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

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Synthesis, electrochemistry and in situ spectroelectrochemistry of novel hexadeca-substituted phthalocyanines with three different groups

et al. 2015

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“…The solubility of Pc compounds can be improved via nonperipheral or peripheral substitution [9][10][11][12][13] . Placing substituents on nonperipheral positions of the Pc ring may reduce the detrimental effect of the substituents on the strong π-π interaction between Pc molecules.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Aggregation behaviors, Antioxidant and Anti-inflammatory activities of Unmetalled and metallophthalocyanines bearing 2(3,4-dimethoxyphenyl)ethanol and 4-Hydroxybenzaldehyde groups

Sulaiman¹

2016

Mediterr.J.Chem.,

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Novel metallophthalocyanines (M: Co, Cu, Ni) containing 2(2-methoxyphenyl)ethanol and 3-Hydroxybenzaldehyde groupsÂ were synthesized and characterized.The structures were confirmed by IR, UV/vis, 1H NMR, 13C NMR, mass spectroscopy Â and elemental analysis. The aggregation behavior of these compounds was investigated in DMSO.Â In addition; the compounds 4-9 were investigated for anti-oxidant activities by super oxide radical; DPPH (2,2-Diphenyl-1-picrylhydrazyl); and hydroxyl radical scavenging assays; in which most of themÂ displayed significant antioxidant activities. Furthermore; compounds 4-9Â Â were evaluated for anti-inflammatory activity by indirect hemolytic and lipoxygenase inhibition assays and revealed good activity.

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“…However, many Pcs have been restricted in application areas owing to their lower solubility and aggregations in common organic solvents [11]. To prepare soluble Pc, the peripheral and/or non-peripheral positions of the Pc ring is attached with functional groups such as bulky or long chain alkyl and alkoxy, crown ether groups, amide or carboxylic acid groups [12][13][14]. In addition, to obtain non-aggregated and soluble Pcs, both axial positions of the central metal ions in the Pc cavity can be attached the various groups [15].…”

Section: Introductionmentioning

confidence: 99%

Toluene vapor sensing characteristics of novel copper(II), indium(III), mono-lutetium(III) and tin(IV) phthalocyanines substituted with 2,6-dimethoxyphenoxy bioactive moieties

Pişkin

Can

Odabaş

et al. 2018

J. Porphyrins Phthalocyanines

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This study presents the synthesis, characterization and toluene sensing properties of copper(II), indium(III) acetate, mono-lutetium(III) acetate and tin(IV) phthalocyanines substituted with 2,6-dimethoxyphenol bioactive groups at the peripheral and non-peripheral positions. The effects of the substituent's position on the toluene vapor detection capabilities of these compounds were investigated. Adsorption data were analyzed by using first-order and Elovich equations in order to investigate the adsorption kinetics. It was found that the kinetics of the toluene adsorption strongly depends on the position of the substituent groups. Our results showed that the Elovich equation fits the experimental data well for non-peripherally substituted Pc based sensors, while the pseudo first-order model best describes the adsorption data for peripheral substituted Pc based sensors. Some physical, photophysical and photochemical of 2,6-dimethoxyphenoxy substituted metal-free and metallophthalocyanines (indium(III) and zinc(II) Pcs) were investigated by our group [26]. We wondered how copper(II), indium(III), mono-lutetium(III) and tin(IV) Pcs substituted with 2,6-dimethoxyphenoxy bioactive moieties affect the physical, electronic and toluene sensing properties. Hence, highly soluble peripherally and non-peripherally substituted Cu(II), In(III), Lu(III) and Sn(IV) Pcs with 2,6-dimethoxyphenoxy were also synthesized (Scheme 1), and the effects of the position of the substituents and the variety of central metal ions on the their spectroscopic and toluene vapors sensing properties were investigated in this study. KEYWORDS EXPERIMENTAL Materials and Equipment2,6-Dimethoxy-phenoxy substituted phthalonitriles (1 and 2) were obtained by the reaction of 2,6-dimethoxy phenol with 3-nitrophthalonitrile or 4-nitrophthalonitrile through base catalyzed nucleophilic aromatic displacement reaction [26]. All other starting materials and solvents used were obtained commercially. All reactions were carried out under dry nitrogen atmosphere. The novel Pcs (3-10) were successively cleaned by washing with hot acetic acid-water solution by volume 7/3, water, ethanol and acetonitrile in the Soxhlet apparatus. Column chromatography was performed on silica gel 60 for a proper purification of the raw compounds. The purity of the products was tested in each step by thin layer chromotography (Silicagel F-254 coated TLC plate). Melting points of the Pc compounds were found to be higher than 300 °C. IR Spectra and electronic spectra were recorded on a Shimadzu FTIR-8300 (ATR) and a Shimadzu UV-1601 spectrophotometer, respectively. Elemental analyses were performed by the Instrumental Analysis Laboratory of TUBITAK-Ankara. Mass spectra were acquired on a Microflex III MALDI-TOF mass spectrometer (Bruker Daltonics, Germany) equipped with a nitrogen UV-Laser operating at 337 nm in reflectron mode with an average of 50 shots. SynthesisGeneral procedure for the synthesis of metallophth alocyanines (3-10).

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A new hexadeca substituted non-aggregating zinc phthalocyanine

Cited by 36 publications

References 25 publications

Synthesis, electrochemistry and in situ spectroelectrochemistry of novel hexadeca-substituted phthalocyanines with three different groups

Synthesis, electrochemistry and in situ spectroelectrochemistry of novel hexadeca-substituted phthalocyanines with three different groups

Synthesis, Characterization, Aggregation behaviors, Antioxidant and Anti-inflammatory activities of Unmetalled and metallophthalocyanines bearing 2(3,4-dimethoxyphenyl)ethanol and 4-Hydroxybenzaldehyde groups

Toluene vapor sensing characteristics of novel copper(II), indium(III), mono-lutetium(III) and tin(IV) phthalocyanines substituted with 2,6-dimethoxyphenoxy bioactive moieties

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