Highly selective oxidation of benzyl alcohol catalyzed by new peripherally tetra-substituted Fe(II) and Co(II) phthalocyanines

Çakır, Volkan; Saka, Ece Tuğba; Bıyıklıoğlu, Zekeriya; Kanteki̇n, Hali̇t

doi:10.1016/j.synthmet.2014.09.022

Cited by 37 publications

(12 citation statements)

References 51 publications

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“…Metallophthalocyanines display typical electronic spectra with two strong absorption regions, one in the UV region at about 300–350 nm (B band) and the other in the visible region at 600–700 nm (Q band) . The electronic absorption spectra of the cobalt and iron phthalocyanines 4 and 5 , in chloroform at room temperature, are shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Co(II) and Fe(II) phthalocyanines: synthesis, investigation of their catalytic activity towards phenolic compounds and electrochemical behaviour

Saka

Bıyıklıoğlu

2015

Applied Organom Chemis

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-[(1-Benzylpiperidin-4-yl)oxy]-substituted cobalt(II) and iron(II) phthalocyanine complexes were synthesized and their catalytic activity towards various phenolic compounds was investigated. Converting from environmentally harmful phenolic compounds into less harmful oxidation products using phthalocyanines makes this study attractive. This catalysis is feasible and timesaving in terms of procedure and the best oxidation conditions determined. Electrochemical studies were also carried out using cyclic voltammetry and square wave voltammetry techniques. Voltammetric analyses of the synthesized phthalocyanine complexes supported their proposed structures.

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Section: Resultsmentioning

confidence: 99%

Co(II) and Fe(II) phthalocyanines: synthesis, investigation of their catalytic activity towards phenolic compounds and electrochemical behaviour

Saka

Bıyıklıoğlu

2015

Applied Organom Chemis

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“…Therefore, three experiments were done at different temperatures in the range of 25-80 • C (entries 6-8). Normally, the reaction temperature has a strong influence on the oxidation of benzyl alcohol and the reaction rate is also reduced due to decrease in reaction temperature [30]. Surprisingly, decreasing temperature did not affect the total conversion of benzyl alcohol, and due to the decrease in temperature benzaldehyde selectivity was gradually increased and finally reached 100% (compare entries 3 and 6-8).…”

Section: Application Of Cobalt(ii) Pc (4) In Benzyl Alcohol Oxidationmentioning

confidence: 96%

“…Catalytic activities towards the oxidation of benzyl alcohol and cyclohexene of some previously reported CoPc catalysts. h of reaction[30]. Özer et al reported the catalytic behavior of novel Co(II) and Pd(II)-perfluoroalkyl Pc complexes for benzyl alcohol oxidation in perfluoromethylcyclohexane (PFMCH) or using different organic-fluorous biphasic systems such as n-hexane-PFMCH, acetone-PFMCH, and toluene-PFMCH.…”

mentioning

confidence: 99%

Peripherally 1,2-dinaphthyl ethanediol substituted phthalocyanine complexes:synthesis, characterization, aggregation, and application in benzyl alcoholoxidation at room temperature

Gök¹,

Yılmaz²

2019

Turk J Chem

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In this study, the synthesis of a novel 1,2-dinaphthyl ethanediol substituted phthalonitrile (2) together with tetra-substituted zinc(II) phthalocyanine (Pc) (3) and cobalt(II) Pc (4) bearing 1,2-dinaphthyl ethanediol at peripheral positions was described. The aggregation behaviors of metallophthalocyanines 3 and 4 in solution were investigated by carrying out Beer-Lambert experiments at different concentrations. In addition, the catalytic activity of new cobalt(II) Pc 4 was investigated for benzyl alcohol oxidation. Benzyl alcohol was converted to benzaldehyde using cobalt(II) Pc 4 as a catalyst by a conversion of 99% with selectivity of 100% at room temperature in 1 h. Several spectroscopic techniques such as FT-IR, UV-Vis, 1 H and 13 C NMR, and MALDI-TOF MS were used for the characterization of the newly synthesized compounds.

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“…Lately performed study with iron(II) phthalocyanine, 29, 30, and the cyclic tetramer consisting of iron(III) phthalocyanine linked to 3,4,9,10-perylenetetracarboxylate, tentatively named FePPOP 31 (Figure 9) indicate the possibility to use these compounds toward catalytic oxidation reaction of benzyl alcohol. In the case of tetramer, it was found that 31 exhibited high stability and also exhibited the large turnover number of the reaction reaching the value of 960 [67][68][69]. However, in the initial phase of the experiment, the catalyst 31 acted much slower in comparison with the other compounds [69].…”

Section: Catalytic Activity and Electrochemical Properties Of Iron Pomentioning

confidence: 99%

Physicochemical Properties and Catalytic Applications of Iron Porphyrazines and Phthalocyanines

Koczorowski¹,

Szczołko²,

Gośliński³

2017

Recent Progress in Organometallic Chemistry

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Porphyrazines and phthalocyanines belong to porphyrinoids, which are macrocyclic compounds consisting of four pyrrole or indole rings, respectively. The aromatic rings of porphyrazines and phthalocyanines are fused together by azamethine bridges (meso nitrogen atoms) in place of methine bridges present in porphyrins. The physicochemical properties of these macrocycles can be modified in two ways. The first is by substitution of metal cation in the core, whereas the second relies on peripheral modification with various substituents. Porphyrazines and phthalocyanines can be modified inside the macrocyclic core with various transition metal cations, including iron(II/III), which impacts their electrochemical properties and influences potential applications in redox reactions. Due to their unique optical and electrochemical properties, porphyrazines and phthalocyanines found many potential and practical applications in medicine and technology. They were mainly researched as photosensitizers in photodynamic therapy, as sensors in biomedical and analytical applications or as building blocks for materials chemistry. This chapter presents physicochemical properties and catalytic applications of iron porphyrazines and phthalocyanines. The first part summarizes the influence of peripheral and axial substituents of iron(II/III) porphyrazines and phthalocyanines on their spectral properties, whereas the second focuses on the electrochemical properties of these molecules. The third part covers the activity of selected iron(II/III) porphyrazines and phthalocyanines of potential value for diverse applications including catalytic reactions.

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Highly selective oxidation of benzyl alcohol catalyzed by new peripherally tetra-substituted Fe(II) and Co(II) phthalocyanines

Cited by 37 publications

References 51 publications

Co(II) and Fe(II) phthalocyanines: synthesis, investigation of their catalytic activity towards phenolic compounds and electrochemical behaviour

Co(II) and Fe(II) phthalocyanines: synthesis, investigation of their catalytic activity towards phenolic compounds and electrochemical behaviour

Peripherally 1,2-dinaphthyl ethanediol substituted phthalocyanine complexes:synthesis, characterization, aggregation, and application in benzyl alcoholoxidation at room temperature

Physicochemical Properties and Catalytic Applications of Iron Porphyrazines and Phthalocyanines

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