Spectrophotometric investigations of protonated forms of heterocyclic compounds

Rozhkova, Yulia; Gurinov, Andrey A.; Орлова, А. О.; Маслов, В. Г.; Shenderovich, Ilya G.; Korotkov, V. I.

doi:10.1134/s0030400x12090135

Cited by 3 publications

(2 citation statements)

References 18 publications

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“…A similar spectrum is observed in organic solvents [32]. AcrH + absorbs below 485 nm [30,33]. However, at high concentrations, AcrH + fluoresced in an aqueous solution at an excitation wavelength of 500 nm at 600 nm (Figure 6a).…”

Section: Resultssupporting

confidence: 70%

The Partner Does Matter: The Structure of Heteroaggregates of Acridine Orange in Water

Shenderovich

2019

Molecules

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Self-assembly of organic molecules in aqueous solutions is governed by a delicate entropy/enthalpy balance. Even small changes in their intermolecular interactions can cause critical changes in the structure of the aggregates and their spectral properties. The experimental results reported here demonstrate that protonated cations of acridine orange, acridine, and acridin-9-amine form stable J-heteroaggregates when in water. The structures of these aggregates are justified by the homonuclear 1H cross-relaxation nuclear magnetic resonance (NMR). The absorption and fluorescence of these aggregates deviate characteristically from the known H-homoaggregates of the protonated cations of acridine orange. The latter makes acridine orange a handy optical sensor for soft matter studies.

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Section: Resultssupporting

confidence: 70%

The Partner Does Matter: The Structure of Heteroaggregates of Acridine Orange in Water

Shenderovich

2019

Molecules

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“…As a result, the mean N…N distance measured in NMR experiments is shorter than that of the most energetically favorable structures obtained in static calculations [146]. This proton tautomerism is slow on the electronic absorption and IR time scales [147,148]. The frequencies of the symmetric and antisymmetric CN vibrations are affected by H-bonding strong enough to discriminate between the spectral pattern of the H-bonded and protonated pyridines [148].…”

Section: The Presence Of a Competing H-bond Can Completely Break The ...mentioning

confidence: 95%

Actual Symmetry of Symmetric Molecular Adducts in the Gas Phase, Solution and in the Solid State

Shenderovich

2021

Symmetry

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This review discusses molecular adducts, whose composition allows a symmetric structure. Such adducts are popular model systems, as they are useful for analyzing the effect of structure on the property selected for study since they allow one to reduce the number of parameters. The main objectives of this discussion are to evaluate the influence of the surroundings on the symmetry of these adducts, steric hindrances within the adducts, competition between different noncovalent interactions responsible for stabilizing the adducts, and experimental methods that can be used to study the symmetry at different time scales. This review considers the following central binding units: hydrogen (proton), halogen (anion), metal (cation), water (hydrogen peroxide).

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Acridine – a Promising Fluorescence Probe of Non-Covalent Molecular Interactions

Rozhkova

Gurinov

Tolstoy

et al. 2013

Zeitschrift Für Physikalische Chemie

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Fluorescence and absorption spectral parameters of acridine have been studied in solution at room temperature in the presence of different proton donors aiming to inspect whether or not acridine can be used as a spectroscopic probe suitable to measure the geometry of hydrogen bonds under different conditions. It has been shown that the most appropriate spectral parameter is the position of fluorescence maximum that changes heavily upon a contraction of the N···H distance. Presumably, also the intensity of the maximum strongly depends on the hydrogen bond geometry. These two parameters can be used to establish two independent, mutually complementary correlations connecting the spectral manifestations and the geometry of hydrogen bond.

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Spectrophotometric investigations of protonated forms of heterocyclic compounds

Cited by 3 publications

References 18 publications

The Partner Does Matter: The Structure of Heteroaggregates of Acridine Orange in Water

The Partner Does Matter: The Structure of Heteroaggregates of Acridine Orange in Water

Actual Symmetry of Symmetric Molecular Adducts in the Gas Phase, Solution and in the Solid State

Acridine – a Promising Fluorescence Probe of Non-Covalent Molecular Interactions

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