Porphyrin acidity and metal ion coordination revisited: electronic substitution effects

Pukhovskaya, S. G.; Нам, Дао Тхе; Ivanova, Yu. B.; Liulkovich, L. S.; Semeikin, А. S.; Сырбу, С. А.; Kruk, M. M.

doi:10.1007/s10847-017-0758-9

Cited by 11 publications

(5 citation statements)

References 18 publications

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“…The coordination site of PpIX with metal ions coincides with the proton removal site of PpIX under alkaline conditions, which makes the three metalloporphyrins more difficult to remove their protons under the same alkaline conditions. This explanation is also consistent with the reported results for other porphyrins in the literature . Then, the change of the fluorescence emission intensity of the three metalloporphyrins with time was measured at pH 8.…”

Section: Resultssupporting

confidence: 91%

“…This explanation is also consistent with the reported results for other porphyrins in the literature. 68 Then, the change of the fluorescence emission intensity of the three metalloporphyrins with time was measured at pH 8. The results showed that the fluorescence emission intensity increased with time, and they approached the maximum after 10, 20, and 20 min for CuPpIX, FePpIX, and ZnPpIX, respectively (Figure S32).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Light-Responsive Fluorescent Security Ink Based on Calixpyridinium–Protoporphyrin IX Disodium Salt Supramolecular Nanoassemblies

Wang

Liu

Gao

et al. 2023

ACS Appl. Nano Mater.

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In this work, the coordination effects of protoporphyrin IX disodium salt (PpIX) with CuII, FeII, and ZnII were systematically studied, and the host–guest interactions of calixpyridinium with PpIX and the three metalloporphyrins were further explored. The bonding ratio between calixpyridinium and PpIX was different from that between calixpyridinium and the other three metalloporphyrins. The reduction of the electronegativity of PpIX caused by the coordination of metal cations may be the reason for the change of the bonding ratio. The reduction of the electronegativity of PpIX caused by the coordination of metal cations also leads to a weaker host–guest interaction with calixpyridinium. The supramolecular nanoassemblies prepared by the host–guest interactions of calixpyridinium with PpIX and the three metalloporphyrins under alkaline conditions could emit a bright fluorescence due to the pH-dependent luminescence characteristics of calixpyridinium and PpIX. Among calixpyridinium and the three metal ions, calixpyridinium alone had the best effect on promoting the photoactivity of PpIX. Its fluorescence gradually disappeared after being irradiated by an incandescent lamp not only in aqueous solution but also on a filter paper. More interestingly, the supramolecular nanoassemblies formed by calixpyridinium and the photoreaction product of PpIX had a reversible temperature responsiveness, which could lead to a reversible fluorescence on–off control. As a result, this material was successfully applied as an intelligent light-responsive fluorescent security ink.

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Section: Resultssupporting

confidence: 91%

Section: ■ Results and Discussionmentioning

confidence: 99%

Light-Responsive Fluorescent Security Ink Based on Calixpyridinium–Protoporphyrin IX Disodium Salt Supramolecular Nanoassemblies

Wang

Liu

Gao

et al. 2023

ACS Appl. Nano Mater.

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“…The ethyl arms substituted in the pyrrole/furan rings activate them, where this in turn initiates the resonance of the O/N lone pair, in order to stabilize the entire macrocycle π-conjugated anion. 51 This is verified by the more pronounced charge increase observed in pyrrole nitrogen atoms i.e., N1/N4 and N2/N5, compared to pyridine nitrogen atoms i.e., N3/N6.…”

Section: Modified Dipyriamethyrin Ligands and Actinide Trichloridesmentioning

confidence: 82%

Computational study of core modified dipyriamethyrin for the competitive complexation of Am³⁺/Cm³⁺ from their trichlorides

Jennifer G,

Schreckenbach,

Varathan

2024

Dalton Trans.

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“…Исследование кислотно-основных свойств порфиринов проводили методом спектрофотометрического титрования. Методики эксперимента и обработки экспериментальных данных подробно представлены в работах [48][49][50]. Ошибка в определении соответствующих констант составляла ± 3-5 %.…”

Section: Introductionunclassified

Spectral and Acid-Base Properties of Tetra-Meso-Alkyl-and Tetra-Meso-Phenyl Substituted Derivatives of Porphyrin

Pukhovskaya¹,

Ivanov²,

Fomina³

et al. 2019

Liq. Cryst. and their Appl.

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Исследованы основные и спектральные свойства серии мезо-замещенных порфиринов с алкильными и арильными заместителями. Квантово-химические расчеты структуры мезо-замещенных порфиринов выполнены в приближении DFT (гибридный функционал B3LYP). Показано, что введение даже четырех объемных заместителей (трет-бутильных групп) вызывает значительные внеплоскостные деформации порфиринового макроцикла и оказывает определяющее влияние на спектральные свойства соединения. Основные свойства порфиринов изучены методом спектрофотометрического титрования в системе ацетонитрил-HClO 4. Определены спектральные параметры молекулярных и протонированных форм для 10 мезо-замещенных порфиринов. Установлено, что для порфиринов с плоской структурой макроцикла природа заместителя оказывает определяющее влияние на основность лиганда. Измерены константы диссоциации катионных форм мезо-замещенных производных порфирина. Показано, что полученные значения pK b находятся в хорошем согласии с классическими представлениями о природе заместителей, даже тех, которые введены не непосредственно в макроцикл, а через фенильный «буфер». Ключевые слова: порфирины, основные свойства, протонированные формы, координационные свойства.

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Porphyrin acidity and metal ion coordination revisited: electronic substitution effects

Cited by 11 publications

References 18 publications

Light-Responsive Fluorescent Security Ink Based on Calixpyridinium–Protoporphyrin IX Disodium Salt Supramolecular Nanoassemblies

Light-Responsive Fluorescent Security Ink Based on Calixpyridinium–Protoporphyrin IX Disodium Salt Supramolecular Nanoassemblies

Computational study of core modified dipyriamethyrin for the competitive complexation of Am³⁺/Cm³⁺ from their trichlorides

Spectral and Acid-Base Properties of Tetra-Meso-Alkyl-and Tetra-Meso-Phenyl Substituted Derivatives of Porphyrin

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Porphyrin acidity and metal ion coordination revisited: electronic substitution effects

Cited by 11 publications

References 18 publications

Light-Responsive Fluorescent Security Ink Based on Calixpyridinium–Protoporphyrin IX Disodium Salt Supramolecular Nanoassemblies

Light-Responsive Fluorescent Security Ink Based on Calixpyridinium–Protoporphyrin IX Disodium Salt Supramolecular Nanoassemblies

Computational study of core modified dipyriamethyrin for the competitive complexation of Am3+/Cm3+ from their trichlorides

Spectral and Acid-Base Properties of Tetra-Meso-Alkyl-and Tetra-Meso-Phenyl Substituted Derivatives of Porphyrin

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Computational study of core modified dipyriamethyrin for the competitive complexation of Am³⁺/Cm³⁺ from their trichlorides