The synthesis, using microwave irradiation and characterization of novel, metal-free and metallophthalocyanines

Acar, İrfan; Kanteki̇n, Hali̇t; Bıyıklıoğlu, Zekeriya

doi:10.1016/j.jorganchem.2009.10.021

Cited by 22 publications

(5 citation statements)

References 26 publications

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“…The NH proton of compound 8 could not be observed owing to the probable strong aggregation of the molecule. 34,35 The 1 H NMR spectrum of zinc phthalocyanine 4 showed the aromatic protons between 7.29 and 7.56 ppm and methylic protons at 2.94-4.41 ppm. 36,37 The tetra-substituted metallo-phthalocyanine complexes (3)(4)(5)(6)(7)(8)(9)(10)(11)(12) showed the phthalocyanine ring protons as unresolved multiplets (most likely due to the presence of isomers).…”

Section: Resultsmentioning

confidence: 99%

Novel Nonmetalated Hydrophobic and Metalated Phthalocyanines Bearing Pyridine-2-Thiol and 2,4,6-Trimethylphenylamine Substituents: Synthesis, Spectroscopic, Aggregation and Thermal Properties

Medyouni

Mansour

Zaghroub

et al. 2016

Journal of Chemical Research

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Novel metal-free and metallo-phthalocyanines, with different substituents at peripheral positions, have been synthesised by cyclotetramerisation of 4- (2,4,6-trimethylphenylamino) phthalonitrile and 4-(pyridine-2-ylsulfanyl)phthalonitrile in the presence of the corresponding divalent metal salts [Zn(II), Cu(II), Co(II) and Ni(II)]. Quaternisation of the metallophthalocyanine functionality produced quaternised cationic Zn, Cu, Ni and Co phthalocyanines, which are soluble in DMF, H 2 O and DMSO. The aggregation behaviour of these compounds was investigated in different concentrations of DMSO. Their thermal stability and electronic stability are reported.

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Section: Resultsmentioning

confidence: 99%

Novel Nonmetalated Hydrophobic and Metalated Phthalocyanines Bearing Pyridine-2-Thiol and 2,4,6-Trimethylphenylamine Substituents: Synthesis, Spectroscopic, Aggregation and Thermal Properties

Medyouni

Mansour

Zaghroub

et al. 2016

Journal of Chemical Research

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“…[39,40] This approach is by far the most represented green synthetic method in literature for the synthesis of phthalocyanines. Microwaveassisted synthesis has successfully provided macrocycles functionalized with halides, [41][42][43][44] terminal alkynes, [45] crown ethers, [46] substituted phenoxy [47][48][49] and 1-naphthyloxy [50] groups, tetraaza, [51] tetraoxamonoaza, [52] tetrathiacyclohexadecane, [53] dithiadiazadioxa, [54] diazadithio [55] and tetrathiadiaza rings, [56,57] thiazoles, [58] functionalized triazoles, [59][60][61][62] phenylthioethanol, [63] monoterpenes like (1R)-(À ) myrtenol and (1R,2S,5R)-(À )menthol, [64] benzenesulfonamide, [65] pyridine [66] and azo compounds. [67] Microwaves have been also employed to synthesize silicon [68] lanthanide(III), [69] lead, [49,70] and platinum [71] derivatives, and phthalocyanine-based polymers.…”

Section: Microwave Irradiationmentioning

confidence: 99%

Phthalocyanines Synthesis: A State‐of‐The‐Art Review of Sustainable Approaches Through Green Chemistry Metrics

Zanotti,

Palmeri,

Raglione

2024

Chemistry A European J

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Driven by escalating environmental concerns, synthetic chemistry faces an urgent need for a green revolution. Green chemistry, with its focus on low environmental impacting chemicals and minimized waste production, emerges as a powerful tool in addressing this challenge. Metrics such as the E‐factor guide the design of environmentally friendly strategies for chemical processes by quantifying the waste generated in obtaining target products, thus enabling interventions to minimize it. Phthalocyanines (Pcs), versatile molecules with exceptional physical and chemical properties, hold immense potential for technological applications. This review aims to bridge the gap between green chemistry and phthalocyanine synthesis by collecting the main examples of environmentally sustainable syntheses documented in the literature. The calculation of the E‐factor of a selection of them provides insights on how crucial it is to evaluate a synthetic process in its entirety. This approach allows for a better evaluation of the actual sustainability of the phthalocyanine synthetic process and indicates possible strategies to improve it.

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“…The modification of different substituents on the periphery can change its conjugation structure. [36][37][38][39][40][41][42][43][44][45][46][47] In recent years, the synthesis of phthalocyanines through metal coordination has attracted more and more attention in the field of catalysis. [48][49][50][51][52][53] However, due to its big ring conjugated structure, it is easy to agglomerate, which significantly diminishes the catalytic impact.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Oxidation of Benzyl Alcohol to Efficiently Synthesize Amide by (−CF₃) Substituted Copper Phthalocyanine Based Composite Catalyst

et al. 2021

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Using a type of tetra‐substituted metal phthalocyanine carbon nanotubes composite material [4 a (OPh‐p‐CF3)CuPc]‐MWCNTs as a catalyst, a method to synthesize benzamides through the oxidative amidation of benzyl alcohol was developed. Synthesize copper phthalocyanine by simple DBU liquid phase catalytic method, and then load phthalocyanine on carbon nanotubes by ultrasound to form four‐substituted metal phthalocyanine carbon nanotubes composite material [4 a (OPh‐p‐CF3)CuPc]‐MWCNTs. The composite materials were detected by ultraviolet visible spectroscopy (UV‐Vis), Fourier transforms infrared spectroscopy (FT‐IR), X‐ray diffraction spectroscopy (XRD), scanning electron microscope (SEM) and transmission electron microscope (TEM). To achieve high‐efficiency and optional catalyze, studied solvent type, oxidant type and dosage, catalyst dosage, time and temperature. In the screening experiment, [4 a (OPh‐p‐CF3)CuPc]‐MWCNTs composite material has high catalytic ability in the oxidation of benzyl alcohol. At the greatest of times, the highest conversion ratio of benzyl alcohol (100 %), selectivity of benzamide (89 %) was obtained. The oxidant was TBHP and the amount was 3 mL, 60 °C for 24 h in DMF. Different kinds of amides were set up by various substituted benzyl alcohols, and good results were obtained.

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The synthesis, using microwave irradiation and characterization of novel, metal-free and metallophthalocyanines

Cited by 22 publications

References 26 publications

Novel Nonmetalated Hydrophobic and Metalated Phthalocyanines Bearing Pyridine-2-Thiol and 2,4,6-Trimethylphenylamine Substituents: Synthesis, Spectroscopic, Aggregation and Thermal Properties

Novel Nonmetalated Hydrophobic and Metalated Phthalocyanines Bearing Pyridine-2-Thiol and 2,4,6-Trimethylphenylamine Substituents: Synthesis, Spectroscopic, Aggregation and Thermal Properties

Phthalocyanines Synthesis: A State‐of‐The‐Art Review of Sustainable Approaches Through Green Chemistry Metrics

Catalytic Oxidation of Benzyl Alcohol to Efficiently Synthesize Amide by (−CF₃) Substituted Copper Phthalocyanine Based Composite Catalyst

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The synthesis, using microwave irradiation and characterization of novel, metal-free and metallophthalocyanines

Cited by 22 publications

References 26 publications

Novel Nonmetalated Hydrophobic and Metalated Phthalocyanines Bearing Pyridine-2-Thiol and 2,4,6-Trimethylphenylamine Substituents: Synthesis, Spectroscopic, Aggregation and Thermal Properties

Novel Nonmetalated Hydrophobic and Metalated Phthalocyanines Bearing Pyridine-2-Thiol and 2,4,6-Trimethylphenylamine Substituents: Synthesis, Spectroscopic, Aggregation and Thermal Properties

Phthalocyanines Synthesis: A State‐of‐The‐Art Review of Sustainable Approaches Through Green Chemistry Metrics

Catalytic Oxidation of Benzyl Alcohol to Efficiently Synthesize Amide by (−CF3) Substituted Copper Phthalocyanine Based Composite Catalyst

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Catalytic Oxidation of Benzyl Alcohol to Efficiently Synthesize Amide by (−CF₃) Substituted Copper Phthalocyanine Based Composite Catalyst