The Synthesis, Characterization, Electrochemical and Spectroelectrochemical Properties of Novel Unsymmetrical Phthalocyanines Containing Naphthoic Acid and Di-tert-butylphenoxy Groups

Köse, Gülşah Gümrükçü; Karaoğlan, Gülnur Keser; Işık, Seher Neccaroğlu; Akyüz, Duygu; Koca, Atıf

doi:10.1016/j.synthmet.2020.116386

Cited by 8 publications

(2 citation statements)

References 46 publications

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“…During the reductionreaction, CuPc gives three reduction couple atÀ 0.77 V,À 1.08 V andÀ 1.81 V, respectively. The Cu 2 + metal center of CuPc complex is redox inactive [39,[43][44][45][46] and it gives reduction couples stem fromPc-based electrochemical behaviors. During the first reduction, CuPc indicated two quasi reversible one-electron reductions atÀ 0.77 V andÀ 1.08 V which reduction couples can be attributed to…”

Section: Electrochemical Studiesmentioning

confidence: 99%

Metallo‐phthalocyanines Containing 1,3,4‐oxadiazole Substituents: Synthesis, Characterization, Electrochemical and Spectroelectrochemical Properties

Akyüz¹,

Demirbaş²,

Bekircan³

2023

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The 4‐[5‐(undecylthio)‐1,3,4‐oxadiazol‐2‐yl)phenol (3)and 4‐(4‐(5‐(undecylthio)‐1,3,4‐oxadiazol‐2‐yl)phenoxy)phthalonitrile (5)were prepared viasubstitution reactions. Metallo‐phthalocyanines (6–9) were obtained by the cyclotetramerization of the phthalonitrile (5). The structures of novel compounds were verified using IR, 1H‐NMR, mass, UV‐Vis methods. Electrochemical characterization of synthesized MPcs (6–9)was carried out by the CV and SWV techniques in DCM/TBAP electrolyte. While MnClPc and CoPc complexes exhibited metal‐based and ring‐based reduction redox couples, CuPc and NiPc gave two ring‐based reduction redox couples. Spectroelectrochemical measurements were performed to observe the color transition during the reduction and oxidation reactions. Thus, the potentials of using the complexes as electrochromic materials were investigated. The CoPc gave the Q band at 667 nm with a shoulder at 663 nm. When the potential was applied to the cell, the intensity of Q band decreased with a shift in wavelength (from 667 nm to 663 nm). In addition, the natural turquoise color (x=0.2720, y=0.3366) of CoPc turned to greenish blue color (x=0.3080, y=0.3461). During the oxidation reactions, CuPc and NiPc gave ring‐based oxidation species. The intensity of Q bands decreased without shift. As a result of the in‐situ spectroelectrochemical measurements, it was observed that CuPc and NiPc, have sharper color transitions and have the potential to be used as electrochromic materials.

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Section: Electrochemical Studiesmentioning

confidence: 99%

Metallo‐phthalocyanines Containing 1,3,4‐oxadiazole Substituents: Synthesis, Characterization, Electrochemical and Spectroelectrochemical Properties

Akyüz¹,

Demirbaş²,

Bekircan³

2023

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“…Manipulation of the phthalocyanines can be done by changing the functional groups on the Pc ring, the central metal or conjugation of the Pc to nanomaterials [6]. The manipulation is done with an idea of improving the chemical and physical properties of the complexes [7].…”

Section: Introductionmentioning

confidence: 99%

Effect of detonation nanodiamonds on the electrocatalytic activity of asymmetric cobalt phthalocyanine: Covalent versus non‐covalent linking

2023

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We report on the effect of detonation nanodiamonds (DNDs) on electrocatalytic properties of an asymmetrically substituted cobalt phthalocyanine (CoPc). The incorporation of DNDs onto cobalt phthalocyanine enhances its electrochemical behaviour. An asymmetrical CoPc alone, when π‐π stacked (CoPc‐DNDs(ππ)) or covalently linked (CoPc@DNDs) to DNDs is used to modify a glassy carbon electrode (GCE) for the electrocatalytic detection of hydrazine. In addition, the GCE was modified by sequentially adding CoPc and DNDs onto its surface, represented as GCE/CoPc‐DNDs(seq) when CoPc is placed before DNDs on the electrode and GCE/DNDs‐CoPc(seq) when DNDs are placed before CoPc, where seq represents sequential. The obtained catalytic rate for the detection of hydrazine on GCE/CoPc@DNDs was 9.3×104 M−1.s−1 with a limit of detection as 0.33 μM. GCE/CoPc@DNDs gave better electrocatalytic activities when compared to its counterparts.

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Synthesis, Electrochemistry, Spectroelectrochemistry, and Electrochromism of Metallophthalocyanines Substituted with Four (2,4,5‐Trimethylphenyl)ethynyl Groups

et al. 2022

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The synthesis of the novel phthalonitrile containing (2,4,5‐trimethylphenyl)ethynyl moieties was performed using the palladium‐catalyzed Sonogashira crosslinking methodology. Cobalt phthalocyanine was obtained with the cyclotetramerization reaction of this dinitrile derivative, while the synthesis of zinc and manganese phthalocyanines was reported by the Sonogashira coupling reaction of the appropriate iodo phthalocyanines. Voltammetric and electrochromic analyses were applied to determine the possible applications of these complexes in different electrochemical/display technologies. The rich redox responses of the complexes had a good influence on the spectroelectrochemical characters of them. Electrochromic measurements of the complexes indicated fast, and reversible color changes with reasonable optical contrasts.

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The Synthesis, Characterization, Electrochemical and Spectroelectrochemical Properties of Novel Unsymmetrical Phthalocyanines Containing Naphthoic Acid and Di-tert-butylphenoxy Groups

Cited by 8 publications

References 46 publications

Metallo‐phthalocyanines Containing 1,3,4‐oxadiazole Substituents: Synthesis, Characterization, Electrochemical and Spectroelectrochemical Properties

Metallo‐phthalocyanines Containing 1,3,4‐oxadiazole Substituents: Synthesis, Characterization, Electrochemical and Spectroelectrochemical Properties

Effect of detonation nanodiamonds on the electrocatalytic activity of asymmetric cobalt phthalocyanine: Covalent versus non‐covalent linking

Synthesis, Electrochemistry, Spectroelectrochemistry, and Electrochromism of Metallophthalocyanines Substituted with Four (2,4,5‐Trimethylphenyl)ethynyl Groups

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