Spectrophotometric study of acid-base and complexing properties of 5,10,15-trinitro-2,3,7,8,12,13,17,18-octaethylporphyrin in acetonitrile

Ivanova, Yu. B.; Нам, Дао Тхе; Чижова, Н. В.; Мамардашвили, Н. Ж.

doi:10.1134/s1070363214060255

Cited by 2 publications

(2 citation statements)

References 8 publications

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“…The strong electron withdrawing nature of the NO 2 moiety polarizes the Por macrocycle, changing its physical and chemical properties . Conversely, nitro groups can also mediate the assembly of supramolecular systems by directly participating in hydrogen bonding with groups such as imidazole or modulating the complexation of the Por with other species in solution . These groups are also widely used in Por chemistry as precursors to amino groups because the latter tend to diminish the synthetic yield of the macrocycle …”

Section: Introductionmentioning

confidence: 99%

“…In analyzing these compounds, we are faced with a significant body of literature offering a range of descriptive frameworks that must be reconciled. These reports all describe several characteristics common to these kinds of compounds, including broad and redshifted absorbance and emission spectra, quenched fluorescence quantum yield, shortened singlet lifetimes, and strong solvent dependence.…”

Section: Introductionmentioning

confidence: 99%

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A Structural Model of Nitro‐Porphyrin Dyes Based on Spectroscopy and Density Functional Theory

et al. 2017

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Nitro-porphyrins are an important class of commercial dyes with a range of potential applications. The nitro group is known to dramatically affect the photophysics of the porphyrin, but there are few systematic investigations of the contributing factors. To address this deficiency, we present spectroscopic studies of a series of nitro-porphyrins, accompanied by density functional theory calculations to elucidate their structures. In particular, we explore how the positions of the substituents affect the energy levels and nuclear geometry. As expected, nitro groups on the meso-phenyl rings cause small changes to the orbital energies by induction, while those at the β-pyrrole positions more strongly conjugate into the aromatic system. In addition, however, we find evidence that β-pyrrole nitro groups distort the porphyrin, creating two non-planar conformations with distinct properties. This unexpected result helps explain the anomalous photophysics of nitro-porphyrins reported throughout the literature, including inhomogeneous line broadening and biexponential fluorescence decay. © 2017 Wiley Periodicals, Inc.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Structural Model of Nitro‐Porphyrin Dyes Based on Spectroscopy and Density Functional Theory

et al. 2017

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Structure, acidic properties and the coordination ability of sapphyrin with an unsymmetric substitution system

Ivanova,

Pukhovskaya,

Lukanov

et al. 2023

J. Porphyrins Phthalocyanines

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Synthesis of unsymmetrically substituted 2,3,7,13,16,17,22,23-octamethyl-8,12-di-[Formula: see text]-butylsapphyrin dichloride (H5P[Formula: see text]Cl[Formula: see text] was carried out. The synthesized compound was identified by electron absorption, 1H NMR spectroscopy, and mass spectrometry. The stability of the anionic complex and the acidic properties of H5P[Formula: see text]Cl2 were studied by spectrophotometric titration. The parameters of the electronic absorption spectra and the concentration range for the existence of deprotonated forms, as well as their acid dissociation constants, are determined. The geometric structure and electronic structure of the molecular and ionic forms of the resulting sapphyrin were calculated in terms of the density functional theory (B3LYP/Def2TZVPP with an empirical correction for GD3 dispersion). The calculations showed good agreement with the experimental data.

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Spectrophotometric study of acid-base and complexing properties of 5,10,15-trinitro-2,3,7,8,12,13,17,18-octaethylporphyrin in acetonitrile

Cited by 2 publications

References 8 publications

A Structural Model of Nitro‐Porphyrin Dyes Based on Spectroscopy and Density Functional Theory

A Structural Model of Nitro‐Porphyrin Dyes Based on Spectroscopy and Density Functional Theory

Structure, acidic properties and the coordination ability of sapphyrin with an unsymmetric substitution system

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