Polycyclic Aromatic Nitrogen Heterocycles. Part V: Fluorescence Emission Behavior of Select Tetraaza- and Diazaarenes in Nonelectrolyte Solvents

Tucker, Sheryl A.; Acree, William E.; Upton, Christopher

doi:10.1366/0003702934048235

Cited by 18 publications

(9 citation statements)

References 21 publications

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“…2,3 The toxicity of several PANHs, 4 normally exceeding that of the structurally related polycyclic aromatic hydrocarbons (PAHs), has motivated the development of analytical methods that, in many cases, must rely on the scarce photophysical information existing for these molecules. 5 Additionally, many authors have hypothesized [6][7][8] that PANHs might also exist beyond the Earth throughout the interstellar medium (ISM), as a result of the reaction between interstellar nitrogen and PAHs. The presence of PAHs in the ISM has long been postulated to account for absorption features in the diffuse interstellar bands (DIBs) [9][10][11] and emission features in the aromatic infrared bands (AIBs).…”

Section: Introductionmentioning

confidence: 99%

“…Polycyclic aromatic nitrogen heterocycles (PANHs) involve a group of compounds widely distributed in the Earth́s biosphere as a consequence of the emission caused by natural fires, incomplete combustion of fuels, and discharge of industrial effluents, among other sources. , The toxicity of several PANHs, normally exceeding that of the structurally related polycyclic aromatic hydrocarbons (PAHs), has motivated the development of analytical methods that, in many cases, must rely on the scarce photophysical information existing for these molecules …”

Section: Introductionmentioning

confidence: 99%

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Photodissociation Electronic Spectra of Cold Protonated Quinoline and Isoquinoline in the Gas Phase

et al. 2017

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Abstract:Photofragmentation electronic spectra of isolated single-isomeric N-protonated quinoline (quinolinium) and isoquinoline (isoquinolinium) ions have been measured at a temperature of 40 K using a mass-selective, 10 cm 1 spectral resolution, photodissociation spectrometer.Additionally, ab-initio adiabatic transition energies calculated using the RI-ADC(2) method have been employed to assist in the assignment of the spectra. Three electronic transitions having * character were clearly evidenced for both protonated ions within the UV and deep-UV spectral ranges. The corresponding spectra at room temperature were previously reported by Hansen et al., 24 together with TD-DFT calculations and a careful analysis of the possible fragmentation mechanisms. This information will be complemented in the present study by appending better resolved spectra, characteristic of cold ions, in which well-defined vibrational progressions associated to the S 1 S 0 and S 3 S 0 transitions exhibit clear 00 bands at h 00 = 27868 and 42230 cm 1 , for protonated quinoline, and at h 00 = 28043 and 41988 cm 1 , for protonated isoquinoline. Active vibrations in the spectra were assigned with the help of calculated normal modes, looking very similar to those of the structurally related protonated naphthalene. Finally, we have observed that the bandwidths associated with the deep-UV S 3 S 0 transition denote a lifetime for the S 3 excited state in the subpicosecond time scale, in contrast with that of S 1 .

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photodissociation Electronic Spectra of Cold Protonated Quinoline and Isoquinoline in the Gas Phase

et al. 2017

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“…Electron-deficient aromatic systems are arousing increasing interest 1 as electron acceptors in organic electronics 2 such as organic 3 photovoltaics. 4,5 1,7-Diazaperylene (1) (benz [de]isoquino [1,8-gh]quinoline, CAS RN 85903-97-5) 6 was the subject of several investigations in this field [7][8][9] because of its high fluorescence quantum yield (83%) 10 and appreciable chemical and photochemical stability. The planar heteroaromatic molecules are densely packed ( cryst = 1.42 Mg•m -3 ) forming a modified herringbone structure.…”

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confidence: 99%

A Three-Step Synthesis of 1,7-Diazaperylene and Derivatives

Langhals¹,

Mayer²,

Polborn³

2020

Synthesis

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“…Polycyclic aromatic nitrogen heterocycles also fluoresce and have been studied with fluorescence quenching techniques. 19–21 Acridine is an example of a PANH whose fluorescence has been quenched using a variety of substances, including silver nanoparticles, 22 carbon nanotubes, 23 and sodium dodecyl sulfate micelles. 24 Acridine orange is another common PANH whose fluorescence has been quenched in different micellar environments 25 and using cadmium sulfide nanoparticles.…”

Section: Introductionmentioning

confidence: 99%

Investigating the Binding of Acridine, Acridine Orange, and Acridine Yellow G to Humic Acid through Fluorescence Quenching

Herb

Anderson

2013

Appl Spectrosc

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A fluorescence quenching method was used to determine the equilibrium binding constants for the association of acridine, acridine orange, and acridine yellow G to humic acid. The fluorescence of each polycyclic aromatic nitrogen heterocycle (PANH) was monitored as aliquots of humic acid were added, and a Stern–Volmer plot was produced in which the slope is the equilibrium constant of the binding reaction. The quenching experiments were performed at temperatures of 30, 35, 40, and 45 °C. A van't Hoff plot generated from the equilibrium binding constants as a function of temperature for a given PANH resulted in a linear plot. Calculation of the ΔHbinding, ΔGbinding, and ΔSbinding for each PANH leads to the conclusion that the equilibrium binding constant, and ΔGbinding, may be predictors of bioavailability. The other thermodynamic quantities, ΔHbinding and ΔSbinding, are helpful in understanding the relative binding of the compounds. For example, acridine yellow G appears to be the least bioavailable of the three PANHs studied because of its strong ΔHbinding = −29.8 kJ/mol, which leads to ΔGbinding = −0.71 kJ/mol. While acridine orange and acridine have similar ΔHbinding values, acridine orange is more likely to bind to humic acid because the ΔSbinding for the process is less negative. Thermodynamic values and equilibrium binding constants for all three compounds are reported.

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Polycyclic Aromatic Nitrogen Heterocycles. Part V: Fluorescence Emission Behavior of Select Tetraaza- and Diazaarenes in Nonelectrolyte Solvents

Cited by 18 publications

References 21 publications

Photodissociation Electronic Spectra of Cold Protonated Quinoline and Isoquinoline in the Gas Phase

Photodissociation Electronic Spectra of Cold Protonated Quinoline and Isoquinoline in the Gas Phase

A Three-Step Synthesis of 1,7-Diazaperylene and Derivatives

Investigating the Binding of Acridine, Acridine Orange, and Acridine Yellow G to Humic Acid through Fluorescence Quenching

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