Spectroelectrochemical Properties Research Articles

Electrochemical polymer synthesis using thiophene and pyrrole/carbazole: Their electrochemical behaviours and capacitor performance

In this study, carbazole-derived monomers were synthesized on ITO-coated PET via electrochemical reactions and conductivity measurements of the resulting polymeric films were performed by UV, FT-IR, NMR, TG-DTG, SEM and AFM analyses. Their spectroelectrochemical properties were investigated. The carbazole (C) based thiophene (Th) polymer abbreviated as pThC and its copolymer with pyrrole (Py), named as pThC-Py were obtained by electrochemical polymerization method. The surface stability of the resulting polymer films was good depending on time. The contact angle (CA) between the water and theco- polymer surface was determined by dropping 6.09 μL of pure water and CA average was calculated as 68.19° < 90°. According to the thermal analysis data of the polymers, the thermal stability of the pThC-Py was better than pThC as it had higher thermal decomposition temperature. Comparisons of electrical conductivity measurements of the polymer films were made depending on the temperature (25, 50 and 90 °C). Due to increasing temperature, the electrical conductivity of pThC-Py film was read as 29.3 S/cm at 90 °C, and also the electrical conductivity values of the pThC-Py were determined as 1.92 × 10−2 S/cm at 25 °C and 14.2 S/cm at 50 °C. Because of the high electrical conductivity of the pThC-Py, its capacitor performance was tried to be determined from cyclic voltammetric measurements. According to the voltammetric results, the power density (P) and the energy density (E) values of the synthesized substance were calculated as 290.532 W/g and 9.684 Wh/g, respectively. This indicates that the amount of energy the material storable is relatively high. Moreover, it is possible to say that it can be included in the classical capacitor class and in the supercapacitor category by improving its features. Moreover, since the electrical conductivity of pThC-Py is quite good, it is thought that it may be suitable for use in electronic devices.

Novel phthalocyanines bearing 4-(2-isopropylphenoxy) groups: Synthesis, characterization, electrochemical and in-situ spectroelectrochemical properties

In this study, 4-(2-isopropylphenoxy)phthalonitrile (3) was prepared via a substitution reaction between 2-isopropylphenol (1) and 4-nitrophthalonitrile (2). Then, peripherally tetra 2-isopropylphenoxy substituted zinc(II) (4) and cobalt(II) (5) phthalocyanines were obtained via a cyclotetramerization reaction between phthalonitrile (3) and related metal salt. The structural characterization of synthesized compounds were completed via FT-IR, 1HNMR , UV–Vis and MALDI-TOF mass data. Electrochemical and spectroelectrochemical measurements were performed to determine the potential of novel phthalocyanines to be used in electrochemical applications. While the cobalt(II) phthalocyanine (5) displayed one metal-based reduction, two ring-based reductions and one metal and ring-based oxidation; zinc(II) phthalocyanine (4) showed three ring-based reductions and one ring-based oxidation reaction. In addition, it was determined that electron-releasing isopropyl phenoxy group affected half-wave peak potentials of complexes and the Q band positions. Diffusion-controlled, reversible and multi-electron transfer abilities of the zinc(II) (4) and cobalt(II) (5) phthalocyanines showed that they have redox richness for can be used in optical technological applications.

A new water−soluble naphthalene diimide as a highly selective fluorescent chemosensor for Cu(II) ion: Synthesis, DFT calculations, photophysical and electrochemical properties

The highly selective, sensitive, and water-soluble fluorescent sensors are desideratum for optoelectronic, environmental, biological, and biomedical applications. An innovative fluorescence chemosensor, naphthalene diimide (3) with metal binding sites, was designed, synthesized and characterized. The chemosensor's optical, electrochemical, spectroelectrochemical, and morphological properties were investigated, and then the density functional theory (DFT) simulations were conducted. The selectivity of 3 for the metals Cu(II), Ag(I), Hg(II), Mg(II), Fe(III), Ca(II), Co(II), Zn(II), Pb(II) and Cd(II) were investigated through UV–visible and fluorescence spectroscopy techniques. 3 was highly selective and sensitive toward Cu(II) metal ions. The chemosensor can detect Cu(II) in water with a detection limit of 1.11 μM, which is lower than the WHO standard and has good repeatability. Further investigations through the IR, DPV, AFM, UV–visible and fluorescence spectroscopies, SEM, EDX and TEM techniques confirmed the binding capabilities of the 3 with Cu(II).

Investigations of the Influence of Two Pyridyl-Mesoionic Carbene Constitutional Isomers on the Electrochemical and Spectroelectrochemical Properties of Group 6 Metal Carbonyl Complexes

Investigations of the Influence of Two Pyridyl-Mesoionic Carbene Constitutional Isomers on the Electrochemical and Spectroelectrochemical Properties of Group 6 Metal Carbonyl Complexes

Integration of a Micro-Transparent heater-integrated electrochemical (μTHE) cell for investigation of the thermal stability of cytochrome c redox variants

Spectroelectrochemistry (SEC) is a powerful technique that combines spectroscopic and electrochemical properties to investigate the redox potential and spectral characterization of chemical or biological molecules. Recently, SEC has gained attention in quantitative analysis, particularly in exploring the role of redox-active proteins in electron transfer networks related to biological systems. The microfluidic technique is used to investigate the spectroelectrochemical properties of the redox potential of metalloproteins under accurate temperature environments. However, conventional heater systems suffer from long ramping times and the transparency of heat systems would influence the spectroscopic information. In this study, we fabricated a micro-transparent heater-integrated electrochemical (μTHE) cell. The μTHE cell allows for spectroelectrochemical studies to investigate the thermal stability of cytochrome c at specific temperatures and the transparent ITO heater integrated into the μTHE cell offers rapid and accurate temperature control during the measurements, avoiding interference with spectroscopic information. The μTHE cell could regulate the oxidation/reduction forms of cytochrome c by the electrochemical process, and the ITO heater provides the precise temperature control for the observation of the absorption spectrum of cytochrome c at different temperatures. By taking advantage of rapid heating and transparency, the μTHE cell offers a facile platform for investigating the spectroelectrochemical properties of redox-active molecules in a well-controlled environment.

Reducing delamination of an electron-transporting polymer from a metal oxide for electrochemical applications.

Delamination of the electron-transporting polymer N2200 from indium tin oxide (ITO) in aqueous electrolytes is mitigated by modifying ITO with an azide-functionalized phosphonic acid (PA) which, upon UV irradiation, reacts with the polymer. The optical, electrochemical, and spectroelectrochemical properties of N2200 thin films are retained in aqueous and non-aqueous media.

Spectroelectrochemical and Computational Study of Quinoline Based Molecules - Potential Anti-Alzheimer’s Drugs

Here, we present combined experimental and theoretical studies on the spectroelectrochemical properties of 8-aminoquinoline (8AQ). 8AQ is a model molecule for drugs that can chelate copper(II) ions, and thus it may find applications in halting the development of Alzheimer’s disease.Although over a hundred years have passed since Alzheimer’s disease (AD) was first described, it remains incurable to this day. According to one of the leading hypotheses, peptides from the β-amyloid (Aβ) group are responsible for the development of AD. By binding copper(II) ions, Aβs form complexes whose presence promotes the formation of harmful, highly active compounds called reactive oxygen species (ROS) and reactive nitrogen species (RNS). In a series of recent studies, we investigated the differences in electrochemical properties of Cu(II)-complexes with the amyloids Aβ(11-16) and Aβ(3-16) with their pyroglutamated versions, pAβ(11-16) and pAβ(3-16). [1,2] These results showed that the pyroglutamate amyloids are conducive to Cu(II)-reduction at a potential associated with ROS production. Given the abundance of pyroglutamated amyloids in senile plaques, this could have important consequences for AD pathophysiology. Overproduction of ROS and RNS can cause neuron death. Therefore, substances that can aid in removing copper(II) ions from β-amyloids could block the formation of ROS and RNS. Recently, a new quinoline derivative with unique properties has undergone preclinical studies. However, little is known about the redox properties of such molecules, which may be crucial in the early stages of testing potential therapeutic substances.Therefore, we aimed to perform electrochemical and spectroelectrochemical studies of a model molecule, 8-aminoquinoline, whose redox properties were not yet well characterized To fully characterize both anodic and cathodic processes, we used cyclic and pulse voltammetry over a wide range of pH values, including physiological (pH=7.4). In addition, the experimental results were supported by DFT-based computational studies exploring the energy landscapes of the possible reactions and advancing understanding of the electrochemical phenomena.The kind of electrochemical tests presented here may prove of crucial importance for the development of more effective drugs against AD. The high failure rate and relatively poor performance of the recently approved treatment indicates the need to extend preclinical studies with new, so far unused techniques, allowing a more complete picture to be obtained of the effectiveness and toxicity of the potential drug candidates.[1] M.Z. Wiloch, N. Baran, M. Jönsson‐Niedziółka, The Influence of Coordination Mode on the Redox Properties of Copper Complexes with Aβ(3‐16) and Its Pyroglutamate Counterpart pAβ(3‐16), ChemElectroChem. 9 (2022). https://doi.org/10.1002/celc.202200623.[2] M.Z. Wiloch, M. Jönsson-Niedziółka, Very small changes in the peptide sequence alter the redox properties of Aβ(11–16)-Cu(II) and pAβ(11–16)-Cu(II) β-amyloid complexes, Journal of Electroanalytical Chemistry. 922 (2022) 116746. https://doi.org/10.1016/j.jelechem.2022.116746.

Toward Camouflage Colors by Electrochemical Copolymerization

AbstractIn this paper, a new electrochromic copolymer containing 6,9‐bis(2,3‐dihydrothieno[3,4‐b][1,4]dioxin‐5‐yl)‐1,2,3,4‐tetrahydrophenazine (EBE) and 4‐(9‐benzyl‐9H‐carbazol‐3‐yl)‐7‐(thiophen‐2‐yl)benzo[c][1,2,5]thiadiazole (CBT) in the main chain was reported. The homopolymers, (Poly(EBE) and Poly(CBT)), were also prepared via electrochemical polymerization and their electrochemical, spectroelectrochemical and electrochromic properties were analyzed in order to compare their properties with those of copolymer (Poly(EBE‐co‐CBT)). The copolymer exhibited good switching property for military camouflage necessities with color change from hues of brown to green. Furthermore, it has been tried to analyze the effects of combination of two donor‐acceptor‐donor (DAD) type monomers with different symmetries on the copolymer properties.

The Influence of an Extended π Electron System on the Electrochemical Properties and Oxidizing Activity of a Series of Iron(III) Porphyrazines with Bulky Pyrrolyl Substituents.

The present study investigates four iron(II/III) porphyrazines with extending pyrrolyl peripheral substituents to understand the impact of introduced phenyl rings on the macrocycle's electrochemical and spectroelectrochemical properties as well as their activity in oxidation reactions. The electrochemical studies showed six well-defined redox processes and quasi-reversible one-electron transfers-two originating from the iron cation and four related to the ring. Adding phenyl rings to the periphery increased the electrochemical gap by 0.1 V. The UV-Vis spectra changes were observed at the applied potential of -1.3 V with the presence of additional red-shifted bands. The oxidizing studies showed increased efficiency in the oxidation reaction of the reference substrate in the cases of Pz1 and Pz2 in both studied oxygen atom donors. The calculated reaction rates in t-BuOOH were 12.0 and 15.0 mmol/min, respectively, for Pz1 and Pz2, compared to 6.4 for Pz3 and 1.8 mmol/min for Pz4. The study identified potential applications for these porphyrazines in mimicking cytochrome P450 prosthetic groups for oxidation and hydroxylation reactions in the future.

Meso carbazole linked Bis-BODIPYs: Design, synthesis, structures and properties

In the present study, BODIPY 4 bearing carbazole ring system at meso position was successfully synthesized as a key building block by the acid-catalyzed condensation reaction of 6-bromo-9-ethyl-9H-carbazole-3-carbaldehyde 3 with 2,4-dimethylpyrrole in one step. The Suzuki and Stille coupling synthetic strategies were subsequently applied to the compound 4 for the construction of a new class of bis-BODIPYs 5 and 6 with extended π-conjugation by introducing phenyl and bithiophene as linkers between two N-ethylcarbazole units. The structures of novel compounds 4–6 were identified by mass, 1H and 13C NMR spectroscopy along with single crystal X-ray diffraction techniques. The photo-physical features of the targeted BODIPYs were investigated via absorption and fluorescence spectroscopies in solvents with different polarity. Photophysical studies reveal important transitions between carbazole and BODIPYs in solution state, which could be controlled by solvent polarity. Crystal geometry of the molecules and the optical band gaps were supported by DFT calculations. Electrochemical and in situ spectroelectrochemical properties of the synthesized compounds were also investigated to reveal electropolymerizable properties and electrochromic potentials of the targeted materials. The results suggested that the compounds 5 and 6 can be potentially used as useful materials in a range of electrochemical research areas.

Investigation of electrochemical and spectroelectrochemical properties of some amino-substituted naphthoquinones (NQs)

The class of quinone compounds are excellent representatives of biologically redox-active compounds. Electron transfers such as in quinone compounds play important roles in the bioactivation of redox-active drugs, in their metabolism/catabolism, and targeted release at precise destinations and frequently promote their ligand–targetinteractions.Owing to the enthralling synthetic importance and pharmacological applications of 1,4-naphthoquinone derivatives, our interest is turned into a detailed electro- and photoelectrochemistry study of these pharmacophoric structures. Firstly, amino(substituted)-1,4-naphthoquinone (NQ) derivatives (2a-b, 3, 4a-b, 5, 6, 7, 8 and 9) were synthesized according to Michael addition mechanism. The exact structures of compounds were elucidated by spectroscopic methods such as FT-IR, 1H-/13C NMR, MS and microanalysis. Secondly, the electrochemical behaviors of NQ derivatives are determined with voltammetric and in situ UV–Vis spectroelectrochemical measurements. All synthesized NQ derivatives illustrate two reductions and one oxidation processes. Voltammetric analyses of the couples of the molecules indicate electrochemical reversibility of the reductions and electrochemical irreversibility of the oxidation couples. Substituent environments of NQ structure considerably influence the chemical reversibility of the redox processes.

Spectro-Electrochemical Properties of A New Non-Enzymatic Modified Working Electrode Used for Histamine Assessment in the Diagnosis of Food Poisoning.

We successfully prepared a non-enzymatic sensor based on a graphene-thiophene composite for histamine detection. The self-assembling properties of the thiophene onto Au support and the high electrical conductivity of graphene encouraged the choice of this type of composite. The composite was deposited via electrochemical polymerization onto the Au layer of a screen-printed microelectrode. The electropolymerization and electrochemical detection of histamine were both achieved by cyclic voltammetry. Two types of electrolytes were used for the electrochemical detection: (a) phosphate buffer solution (PBS), which showed low-intensity redox peaks for histamine; and (b) trichloroacetic acid (TCA) 0.01 M, which showed improved results over PBS and did not damage the microelectrode. For the concentration range of 100-200 mg/kg, the sensor shows a linear regression pattern for the oxidation peak fitted on the equation Ipa = 123.412 + 0.49933 ×x, with R2 = 0.94178. The lowest limit of detection was calculated to be 13.8 mg/kg and the limit of quantification was calculated at 46 mg/kg. These results are important since by monitoring the amount of histamine in a food product, early onset of spoilage can be easily detected, thus reducing foodborne poisoning and food waste (by recycling products that are still edible).

Electrochemical and In-situ spectroelectrochemical properties of novel mononuclear 2,4-di-tert-butyl-6-(3,4-dicyanophenoxy)phenolate substituted metallophthalocyanine compounds

In this study, the synthesis and characterization of a series of novel tetra substituted highly soluble metallophthalocyanines [M = CoII, FeIII, MnIII, NiII and ZnII] derivatives bearing 2,4-di-tert-butyl-6-(3,4-dicyanophenoxy)phenolate groups on the peripheral positions are reported. These phthalocyanine (Pc) compounds can be used as new starting materials for the synthesis of dinuclear ball-type Pcs due to the involvement of four phthalonitrile rings as closable end groups in their molecules. The assignment of the redox processes of these compounds indicated that CoII, FeIII, and MnIII centers into the Pc core increased the redox richness of the complexes, with the addition of metal-based electron transfer processes to the ring-based ones while NiPc and ZnPc show only ring-based electron transfer processes. These ball-type Pc precursor compounds exhibited a unique character also as a result of eight redox-active nitrile end groups on the peripheral tails of the Pc core. Thus, electrochemical and spectroelectrochemical properties of metallophthalocyanine complexes were analysed, also in comparison to their previously reported (5-(tert-butyl)-2-((3,4-dicyanophenoxy)methyl)phenyl)methanolate substituted analogues to determine the influence of metal centers and substituents in the periphery. Altering the metal center of the Pc ring as incorporation of a redox active metal center and changing the positions of the substituents slightly affected the potentials for nitrile and Pc ring redox processes. However, the spectral and color responses of the complexes were significantly influenced by the nature of central metal and peripheral substituents. As an important reflection, the electron transfer processes of the complexes and the connection between the electrochemically generated anionic and cationic species originated distinct spectral and color changes, identified with in-situ spectroelectrochemical measurements in solution medium. These measurements pointed out their potential applicability in the fields of the opto electronic technologies.

Electrochemical and In-situ exhibited spectroelectrochemical properties of novel 4,4′-(3,5-di-tert-butyl-1,2-phenylene)bis(oxy) substituted ball-type phthalocyanine compounds

In this study, binuclear ball-type metallophthalocyanine compounds Co2Pc2(2), Fe2(OAc)2Pc2(3), Mn2(OAc)2Pc2(4), Ni2Pc2(5), Zn2Pc2(6) were obtained by using 4,4′-((3,5-di-tert-butyl-1,2-phenylene)bis(oxy))diphthalonitrile, and metal salts (mol ratio of metal salts and ligand:5/1), and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a catalyst in 0.25 mL dimethylethanolamine at reflux temperature for about 20 min. Phthalocyanines have shown high solubility in common organic solvents since they contain eight bulky butyl groups and showed minimal aggregation in common solvents. The chemical structure of the complexes and their precursor has been characterized by spectral methods and elemental analysis. Electron transfer properties of all ball-type metallophthalocyanines were studied by using electrochemical and in-situ spectroelectrochemical measurements in non-aqueous media. Two kinds of electron transfer processes, i.e., metal-based and phthalocyanine ring-based redox processes, were revealed by these complexes. The electrochemical experiments displayed the establishment of discrete mixed-valenced oxidized as well as reduced groups resulting from intramolecular interactions between the two phthalocyanines and two metal units in novel ball-type complexes. Advanced redox properties of these complexes developed noticeable spectral and color changes, detected by in-situ spectroelectrochemical measurements in a solution medium.

Visible Light–Near-Infrared Dual-Band Electrochromic Device

We herein propose a proof of concept of a full dual-band electrochromic (EC) device able to selectively modulate solar light between 300 and 1600 nm. Dual-band control was achieved by exploiting the complementarity and cooperation of two earth-abundant and nontoxic transition metal oxide nanocrystalline materials able to absorb two different spectral regions when electrochemically charged. The active materials were obtained through a microwave-based synthetic protocol able to produce massive amounts of ligand-free water-soluble TiO2@WO3–x colloidal heterostructured nanocrystals. The inorganic heterostructures were deposited via a spray-coating airbrushing method. Graphene was adopted as a near-infrared (NIR) transparent material for the realization of conductive substrates. The nano-dimensions and stable solubility of active materials during the deposition process endorse the development of scattering-free nanostructured electrodes and high device transparency under open-circuit conditions, respectively. The spectro-electrochemical properties of the as-made nanostructured electrodes were evaluated in relation to pure WO3–x and TiO2 single nanomaterials and a blend of these. The heterostructured architecture ensures a lower optical haze (around 8% of total radiation) as against the blend, contributing to improving the overall EC performance. The TiO2@WO3–x-based device shows 67% NIR shielding while preserving 60% of visible (VIS) transparency under cool-mode conditions and 89% screening of VIS and NIR radiation under the dark mode. These results represent an important step forward in the development of scalable dual-band EC devices.

Ruthenium Complexes of Polyfluorocarbon Substituted Terpyridine and Mesoionic Carbene Ligands: An Interplay in CO2 Reduction.

In recent years terpyridines (tpy) and mesoionic carbenes (MIC) have been widely used in metal complexes. With the right combination with a metal center, both of these ligands are individually known to generate excellent catalysts for CO2 reduction. In this study, we combine the potentials of PFC (PFC=polyfluorocarbon) substituted tpy and MIC ligands within the same platform to obtain a new class of complexes, which we investigated with respect to their structural, electrochemical and UV/Vis/NIR spectroelectrochemical properties. We further show that the resulting metal complexes are potent electrocatalysts for CO2 reduction in which CO is exclusively formed with a faradaic efficiency of 92 %. A preliminary mechanistic study, including the isolation and characterization of a key intermediate is also reported.

Spectroscopic and Spectroelectrochemical Studies of Hexapentyloxytriphenylene-A Model Discotic Molecule.

The electrochemical and spectroelectrochemical properties of the discotic mesogen 2,3,6,7,10,11-pentyloxytriphenylene (H5T) were studied with the use of cyclic voltammetry combined with UV-Vis and electron paramagnetic resonance (EPR) spectroscopy in solution. The UV-Vis absorption spectroscopy of H5T in dichloromethane showed its monomeric state in a concentration range up to 10-3 mol dm-3. The reversible process of the electrochemical formation of the radical cation was evidenced within the experimentally accessible potential window. The in situ UV-Vis spectroelectrochemical measurements further enabled identification of the product of the redox process and evaluation of the effect of aggregation in the concentration range of 5 × 10-3 mol dm-3. The results are discussed in the frame of solvent effects on the self-assembly propensity of solute molecules, in a wide range of concentrations. In particular, the crucial role of the solvent polarity is indicated, which contributes to the understanding of solution effects and pre-programming of supramolecular organic materials, in particular anisotropic disc-shaped hexa-substituted triphenylenes.

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

AbstractThe 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.

Synthesis and Spectroelectrochemical Investigation of Anodic Black TiOx Nanotubes

Anodic TiO2 nanotubes were transformed into anatase at 400 °C for 2 h in air and subjected to electrochemical reduction at different conditions. It revealed that the reduced black TiOx nanotubes were not stable in contact with air; however, their lifetime was considerably extended to even a few hours when isolated from the influence of atmospheric oxygen. The order of polarization-induced reduction and spontaneous reverse oxidation reactions were determined. Upon irradiation with simulated sunlight, the reduced black TiOx nanotubes generated lower photocurrents than non-reduced TiO2, but a lower rate of electron-hole recombination and better charge separation were observed. In addition, the conduction band edge and energy level (Fermi level), responsible for trapping electrons from the valence band during the reduction of TiO2 nanotubes, were determined. The methods presented in this paper can be used for determination of the spectroelectrochemical and photoelectrochemical properties of electrochromic materials.

Electrochemical, spectroelectrochemical, and electrocatalytic properties of novel soluble phthalocyanines containing peripheral thymoxy and chloride units

Novel CoPc, CuPc, Fe(OAc)Pc and Mn(Cl)Pc were synthesized by using original 4-chloro-5-(2-isopropyl-5-methylphenoxy)phthalonitrile in order to investigate their potential redox applications suitable with their chemical and physical characteristics. The molecular structures of new compounds were determined with spectroscopic methods such as elemental analysis, FT-IR, UV–vis, NMR and MALDI TOF MS. Redox behaviours of Fe(OAc)Pc and Mn(Cl)Pc complexes have been probed by using diverse voltammetric techniques such as cyclic (CV) and square wave voltammetry (SWV). In addition, the colour alterations accompanying spectral changes were perused concurrently with electrocolorimetric measurements, and electrocatalytic efficiencies of the all compounds were perused in oxygen reduction reaction.