Spectroscopic, Electrochemical, Magnetic and Structural Characterization of an Hexamethylenetetramine Co(II) Porphyrin Complex – Application in the Catalytic Degradation of Vat Yellow 1 dye

Nasri, Soumaya; Hajji, Melek; Guergueb, Mouhieddinne; Dhifaoui, Selma; Marvaud, Valérie; Molton, Florian; Roisnel, Thierry; Guerfel, Taha; Nasri, Habib

doi:10.1016/j.molstruc.2020.129676

Cited by 15 publications

(10 citation statements)

References 78 publications

(70 reference statements)

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“…FT-IR ( Figure S1, Supplementary Material ) and UV-vis absorption ( Figure 1 ) and 1 H NMR data ( Figure S2 ) agree with the reported data [ 51 ]. In keeping with the paramagnetic character of the Co(II) d 7 system, we obtained broadened 1 H NMR signals at δ = 15.71 ppm for the β-pyrrole protons and at 12.96 and 9.92 ppm for the phenyl atoms [ 10 , 11 , 26 , 54 , 78 ].…”

Section: Resultsmentioning

confidence: 99%

“…By variation of the substituents on the phenyl core of the porphyrin ligands, these processes can cover a huge range of potentials [ 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 ]. Moreover, there are one or two axial positions available for binding small molecules [ 10 , 11 , 12 , 26 , 27 , 28 , 29 ]. Both properties make Co porphyrins very suitable for redox catalysis [ 22 , 23 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 ].…”

Section: Introductionmentioning

confidence: 99%

“…Amongst other organic redox transformations, the electrochemically or photochemically initiated decomposition of organic dyes in waste water is another increasingly important research field in recent years [ 5 ]. Recently, Zn(II) [ 12 , 15 , 71 , 72 ] and Co(II) porphyrins [ 10 , 11 , 26 , 73 ] have been used as catalysts in the degradation of organic dyes with H 2 O 2 . In view of the first oxidation potential of Co(TPP) complexes lying in the range of 0.1 to 0.75 V vs. SCE [ 10 , 11 , 13 , 16 , 17 , 22 , 24 , 25 , 26 , 61 , 62 ], their high reactivity in radical-based organic transformations [ 14 , 58 , 59 , 60 ] is not unexpected and a very recent study on a (5,10,15,20-tetrakis(2,5-dimethoxyphenyl)porphyrinato)cobalt(II) has revealed some mechanistic details in such decomposition reactions using H 2 O 2 [ 73 ].…”

Section: Introductionmentioning

confidence: 99%

“…By variation of the substituents on the phenyl core of the porphyrin ligands, these processes can cover a huge range of potentials [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25]. Moreover, there are one or two axial positions available for binding small molecules [10][11][12][26][27][28][29]. Both properties make Co porphyrins very suitable for redox catalysis [22,23,[30][31][32][33][34][35][36][37][38][39][40][41][42][43][44].…”

Section: Introductionmentioning

confidence: 99%

“…Recently, Zn(II) [12,15,71,72] and Co(II) porphyrins [10,11,26,73] have been used as catalysts in the degradation of organic dyes with H 2 O 2 . In view of the first oxidation potential of Co(TPP) complexes lying in the range of 0.1 to 0.75 V vs. SCE [10,11,13,16,17,22,[24][25][26]61,62], their high reactivity in radicalbased organic transformations [14,[58][59][60] is not unexpected and a very recent study on a (5,10,15,20-tetrakis(2,5-dimethoxyphenyl)porphyrinato)cobalt(II) has revealed some mechanistic details in such decomposition reactions using H 2 O 2 [73].…”

Section: Introductionmentioning

confidence: 99%

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CO2 to CO Electroreduction, Electrocatalytic H2 Evolution, and Catalytic Degradation of Organic Dyes Using a Co(II) meso-Tetraarylporphyrin

et al. 2022

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The meso-tetrakis(4-(trifluoromethyl)phenyl)porphyrinato cobalt(II) complex [Co(TMFPP)] was synthesised in 93% yield. The compound was studied by 1H NMR, UV-visible absorption, and photoluminescence spectroscopy. The optical band gap Eg was calculated to 2.15 eV using the Tauc plot method and a semiconducting character is suggested. Cyclic voltammetry showed two fully reversible reduction waves at E1/2 = −0.91 V and E1/2 = −2.05 V vs. SCE and reversible oxidations at 0.30 V and 0.98 V representing both metal-centred (Co(0)/Co(I)/Co(II)/Co(III)) and porphyrin-centred (Por2−/Por−) processes. [Co(TMFPP)] is a very active catalyst for the electrochemical formation of H2 from DMF/acetic acid, with a Faradaic Efficiency (FE) of 85%, and also catalysed the reduction of CO2 to CO with a FE of 90%. Moreover, the two triarylmethane dyes crystal violet and malachite green were decomposed using H2O2 and [Co(TMFPP)] as catalyst with an efficiency of more than 85% in one batch.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

CO2 to CO Electroreduction, Electrocatalytic H2 Evolution, and Catalytic Degradation of Organic Dyes Using a Co(II) meso-Tetraarylporphyrin

et al. 2022

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Modulating the oxygen affinity of porphyrins with metals, ligands, and functional groups: A DFT study

Ovalle,

Malardier‐Jugroot

2024

J Comput Chem

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The interaction between different metals (M), axial ligands (L), and ring substituents (R) in porphyrins was investigated using density functional theory. Different combinations of iron and cobalt as metal centers; imidazole, chlorine, and an n‐heterocyclic carbene (NHC) as axial ligands, and unsubstituted, octaethyl‐, and tetraphenyl‐porphyrins were explored in their low, intermediate, and high‐spin states, alongside oxygen affinity. Remarkably, the n‐heterocyclic carbene enhanced the affinity of cobalt porphyrins to oxygen, with binding energies on average 4.4 kcal mol−1 higher than FeP with the same ligand, and 0.78 kcal mol−1 higher than FeP with imidazole. The planarity of the iron tetraphenyl porphyrin with imidazole compared to its ruffled cobalt counterpart is noteworthy in both oxy‐ and deoxy‐forms, highlighting imidazole's stabilizing influence on the porphyrin structure, particularly iron porphyrins, alongside imidazole's stabilizing effect on the affinity to O2. Despite the significant non‐planarity induced by NHC as an axial ligand ‐regardless of the metal or ring substituent used‐, it did not hinder the affinity of CoP to O2 (14.26 kcal mol−1, on average) as it did with the FeP with NHC (9.88 kcal mol−1, on average). Cobalt porphyrins with n‐heterocyclic carbene ligands show promising potential for O2 activation or oxygen transport applications. The results show the complex interactions between the different parts of metalloporphyrins and highlight the capability of tailoring their affinity to O2. It also exemplifies the stabilizing effect of imidazole on the porphyrins, providing a very narrow range of binding energies and smaller differences in their geometries.

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Probing the significance, nature, and energetics of weak hydrogen bonding in the crystal structure of a 1-chloro-4-methoxybenzene derivative through structural and computational modeling

Haouas

2023

Chem. Pap.

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Spectroscopic, Electrochemical, Magnetic and Structural Characterization of an Hexamethylenetetramine Co(II) Porphyrin Complex – Application in the Catalytic Degradation of Vat Yellow 1 dye

Cited by 15 publications

References 78 publications

CO2 to CO Electroreduction, Electrocatalytic H2 Evolution, and Catalytic Degradation of Organic Dyes Using a Co(II) meso-Tetraarylporphyrin

CO2 to CO Electroreduction, Electrocatalytic H2 Evolution, and Catalytic Degradation of Organic Dyes Using a Co(II) meso-Tetraarylporphyrin

Modulating the oxygen affinity of porphyrins with metals, ligands, and functional groups: A DFT study

Probing the significance, nature, and energetics of weak hydrogen bonding in the crystal structure of a 1-chloro-4-methoxybenzene derivative through structural and computational modeling

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