The quest for a better understanding of ethanol coordination to magnesium and zinc porphyrin: A combined experimental and theoretical study

Borah, Bhargab; Majumder, Smita; Borah, Karishma Devi; Bhuyan, Jagannath

doi:10.1016/j.molstruc.2020.129646

Cited by 6 publications

(3 citation statements)

References 54 publications

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“…5. These observations suggest that aggregative processes of the porphyrins might play a role in loss of activity in water since both TPPS and TEG 12 PZn undergo aggregation in solution – for the former through J -aggregation 42 and for the latter through coordinative interactions 43 involving ethylene glycol substituents and Zn( ii ) coordinated at the porphyrin moiety. The profound loss of activity in TEG 12 PZn suggests decomposition or photobleaching (details of these matter will be reported elsewhere).…”

Section: Resultsmentioning

confidence: 97%

Nonionic omnisoluble photosensitizer reference material for the estimation of singlet oxygen quantum yield

Payne

Hynek

Labuta

et al. 2022

Phys. Chem. Chem. Phys.

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Section: Resultsmentioning

confidence: 97%

Nonionic omnisoluble photosensitizer reference material for the estimation of singlet oxygen quantum yield

Payne

Hynek

Labuta

et al. 2022

Phys. Chem. Chem. Phys.

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“…We have also calculated the chemical hardness (η), chemical potential (μ), chemical electrophilicity index (ω) and softness (s) for both complex 1 a and 1 b (Table 2). The global indices were calculated using energy calculation data of the optimized structure of the complex 1 a and complex 1 b by standard formula [40–43] . From the calculation, complex 1 a is found as harder than 1 b as it has higher chemical hardness and lower softness value.…”

Section: Resultsmentioning

confidence: 99%

Quest for Zinc Methoxyisoporphyrin Molecules: Experimental and Theoretical Studies

Borah¹,

Yamang²,

Singh³

et al. 2022

ChemistrySelect

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This study describes the synthesis, characterization and theoretical studies of two new zinc isoporphyrin compounds, [5‐(methoxy)‐5,10,15,20‐tetrakis(4‐hydroxy)‐5,15H‐porphinato]zinc(II) 1 b, and [5‐(methoxy)‐5,10,15,20‐tetrakis(4‐methyl)‐5,15H‐porphinato]zinc(II) 2 b. Meso‐tetra(4‐hydroxyphenyl)zinc porphyrin, [ZnT(4‐OH)PP], 1 a and, meso‐tetra(4‐methylphenyl)zinc porphyrin, [ZnT(4‐CH3)PP] 2 a were used as a parent porphyrins to synthesize the respective isoporphyrin complexes in the presence of ceric ammonium nitrate (CAN) in methanol medium. The synthesized isoporphyrin compounds are characterized using all standard spectroscopic techniques like UV‐Visible, IR, 1HNMR, and ESI‐Mass spectrometric method. Theoretical calculations at the DFT level was performed to understand the properties and reactivity of the isoporphyrins. To get some insight into the mechanism of isoporphyrin formation via zinc porphyrin dication, the geometry of zinc porphyrin dication [ZnT(4‐OH)PP]++ was optimized and the distribution of Mulliken charge in the dication ring was calculated. The higher positive charge at the meso C‐atoms of the zinc porphyrin dication with respect to other ring carbon atoms supports the proposed nucleophilic attack at the meso carbon of the dication. The DFT calculations studied here is suitable to understand the mechanism of formation of isoporphyrins in the presence of nucleophiles, unique electronic spectra, and redox properties of isoporphyrins.

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“…During measurements to assess ΦSO of TEG12PZn, it was found that irradiation of its solutions led to the rapid (within 120 s) and irreversible loss of their singlet oxygen generating capacity as shown in Figure 5. These observations suggest that aggregative processes of the porphyrins might play a role in loss of activity in water since both TPPS and TEG12PZn undergo aggregation in solution -for the former through J-aggregation 37 and for the latter through coordinative interactions 38 involving ethylene glycol substituents and Zn(II) coordinated at the porphyrin moiety. The profound loss of activity in TEG12PZn suggests decomposition or photobleaching (details of these matter will be reported elsewhere).…”

Section: Singlet Oxygen Generationmentioning

confidence: 96%

Simple Nonionic Omnisoluble Tetraphenylporphyrin for Relative Referencing of Singlet Oxygen Quantum Yield

Payne

Hynek

Labuta

et al. 2021

Preprint

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Meso-tetrakis-(3,4,5-tris{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}phenyl)porphyrin TEG12PH2 is reported as an ‘omnisoluble’ TPP reference for singlet oxygen (1O2) generation quantum yield (ΦSO) estimation. TEG12PH2 is a highly soluble, nonionic compound possessing excellent 1O2 QY in a wide variety of common solvents, including water. TEG12PH2 was prepared on multigram scale by the 12-way O-alkylation of tetrakis(3,4,5-trihydroxyphenyl)porphyrin using 2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-toluenesulfonate as reaction solvent. The corresponding Zn(II) complex TEG12PZn was also prepared and studied. Its 1O2 QYs in the different solvents studied were found to be 0.86 (acetone), 0.59 (acetonitrile), 0.66 (chloroform), 0.85 (methanol), 0.45 (toluene) and 0.51 (water). TEG12PH2 can be considered a reliable and easy to implement omnisoluble reference compound for the estimation of the 1O2 generating activities of new materials, especially new porphyrinic compounds.

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The quest for a better understanding of ethanol coordination to magnesium and zinc porphyrin: A combined experimental and theoretical study

Cited by 6 publications

References 54 publications

Nonionic omnisoluble photosensitizer reference material for the estimation of singlet oxygen quantum yield

Nonionic omnisoluble photosensitizer reference material for the estimation of singlet oxygen quantum yield

Quest for Zinc Methoxyisoporphyrin Molecules: Experimental and Theoretical Studies

Simple Nonionic Omnisoluble Tetraphenylporphyrin for Relative Referencing of Singlet Oxygen Quantum Yield

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