Electronic nature and structure of aggregates of riboflavin molecules

Astanov, S.; Kasimova, Guzal; Kurtaliev, Eldar N.; Nizomov, N.; Jumabaev, А.

doi:10.1016/j.saa.2020.119177

Cited by 10 publications

(8 citation statements)

References 40 publications

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“…Unsurprisingly, the extensive solution-phase photochemical behaviour of riboflavin has accrued much experimental attention over the years [ 1 , 5 ]; however, studies of its intrinsic (i.e., gas-phase) excited-state properties, and those of other flavins, have been sparse until very recently [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. To date, the only gas-phase study of a system involving riboflavin is that of Dopfer and co-workers on alkali metal coordination [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

“…This ensures that photofragments observed are produced from the species of interest, and not from a minor component of the solution-phase mixture. Furthermore, the solution environment is potentially much more complex, since direct photoproducts can undergo secondary reactions and will be subject to environmental factors, i.e., pH, solvent, and aggregation [ 5 , 16 , 17 , 18 , 19 , 20 ]. Herein, we evaluate the benefits of this two-step methodology for studying photochemistry by applying it to RF in its native solution-phase form, [RF − H] − We have chosen RF for this study since it’s solution photochemistry has been well studied, thus allowing us to benchmark our solution-phase on-line photolysis technique and also understand if the gas-phase measurements can shed light on the solution-phase photochemistry.…”

Section: Introductionmentioning

confidence: 99%

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Photodegradation of Riboflavin under Alkaline Conditions: What Can Gas-Phase Photolysis Tell Us about What Happens in Solution?

2021

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The application of electrospray ionisation mass spectrometry (ESI-MS) as a direct method for detecting reactive intermediates is a technique of developing importance in the routine monitoring of solution-phase reaction pathways. Here, we utilise a novel on-line photolysis ESI-MS approach to detect the photoproducts of riboflavin in aqueous solution under mildly alkaline conditions. Riboflavin is a constituent of many food products, so its breakdown processes are of wide interest. Our on-line photolysis setup allows for solution-phase photolysis to occur within a syringe using UVA LEDs, immediately prior to being introduced into the mass spectrometer via ESI. Gas-phase photofragmentation studies via laser-interfaced mass spectrometry of deprotonated riboflavin, [RF − H]−, the dominant solution-phase species under the conditions of our study, are presented alongside the solution-phase photolysis. The results obtained illustrate the extent to which gas-phase photolysis methods can inform our understanding of the corresponding solution-phase photochemistry. We determine that the solution-phase photofragmentation observed for [RF − H]− closely mirrors the gas-phase photochemistry, with the dominant m/z 241 condensed-phase photoproduct also being observed in gas-phase photodissociation. Further gas-phase photoproducts are observed at m/z 255, 212, and 145. The value of exploring both the gas- and solution-phase photochemistry to characterise photochemical reactions is discussed.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photodegradation of Riboflavin under Alkaline Conditions: What Can Gas-Phase Photolysis Tell Us about What Happens in Solution?

2021

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“…In this case, trans-sic isomerization can occur under the influence of UV irradiation, while cis→trans can occur arbitrarily. Such properties of arylethylene can be used in the reception and analysis of information in molecular computers [5]. The authors [6] have shown that high-molecular polyenes and diarylethylenes in combination with iodine can be electrically conductive and they can be used as micro-or nanowire diphenylethylene molecules also have physiological active properties, while they are antimicrobial and antioxidants.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic features of diphenylaryethylenes and arylpolyenes having substituted groups in pairs

Astanov

Kasimova

Shamsiev

2022

J. Phys.: Conf. Ser.

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The spectral and optical characteristics of 4,4′ substituted stilbene and diphenylpolyenes were determined depending on the nature of the substituents. It is established that as a result of the dipole-dipole interaction of Van der Waals forces and the entrainment of the electron energies of molecules in the studied compounds, a botochromic shift of the adsorption and luminescence spectra is carried out. It is determined that for 4,4′ substituted arylethylene molecules with protonadonnor substituted groups, high values of the quantum yield of luminescence are observed, which are recommended for their use as fluorescence probes.

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“…80 fold in alkaline media (correlated with the increased reactivity of the triplet state) until pH 10, when the anion is formed [4]. Unsurprisingly, the extensive solution-phase photochemical behavior of riboflavin has accrued much experimental attention over the years [1,5]; however, studies of its intrinsic (i.e., gas-phase) excited-state properties, and those of other flavins, have been sparse until very recently [6][7][8][9][10][11][12][13]. To date, the only gas-phase study of a system involving riboflavin is that of Dopfer and co-workers on alkali metal coordination [9].…”

Section: Introductionmentioning

confidence: 99%

“…The benefit of this approach is that the solution-phase measurements probe a more "real-world" environment for the riboflavin vitamin (e.g., when it is in milk or within a cosmetic formulation), while the gas-phase measurements aid the understanding of the solution-phase photochemical mechanisms. The solution-phase environment is potentially much more complex, since direct photoproducts can undergo secondary reactions and will be subject to environmental factors, i.e., pH, solvent, and aggregation [5,[16][17][18][19][20]. This two-step method provides a new approach that could be widely applied to characterize the photochemical breakdown of food, beauty, and pharmaceutical products.…”

Section: Introductionmentioning

confidence: 99%

Photodegradation of Riboflavin under Alkaline Conditions: What can Gas-Phase Photolysis Tell Us About What Happens in Solution?

Wong¹,

Rhodes²,

Dessent³

2021

Preprint

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The application of electrospray ionization mass spectrometry (ESI-MS) as a direct method for detecting reactive intermediates is a technique of developing importance in the routine monitoring of solution-phase reaction pathways. Here, we utilize a novel on-line photolysis ESI-MS approach to detect the photoproducts of riboflavin in aqueous solution under mildly alkaline conditions. Riboflavin is a constituent of many food products, so its breakdown processes are of wide interest. Our on-line photolysis setup allows for solution-phase photolysis to occur within a syringe using UVA LEDs, immediately prior to being introduced into the mass spectrometer via ESI. Gas-phase photofragmentation studies via laser-interfaced mass spectrometry of deprotonated riboflavin, [RFH], the dominant solution-phase species under the conditions of our study, are presented alongside the solution-phase photolysis. The results obtained illustrate the extent to which gas-phase photolysis methods can inform our understanding of the corresponding solution-phase photochemistry. We determine that the solution-phase photofragmentation observed for [RFH] closely mirrors the gas-phase photochemistry, with the m/z 241 ion being the only major condensed-phase photoproduct. Further gas-phase photoproducts are observed at m/z 255, 212, and 145. The value of exploring both the gas- and solution-phase photochemistry to characterize photochemical reactions is discussed.

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Electronic nature and structure of aggregates of riboflavin molecules

Cited by 10 publications

References 40 publications

Photodegradation of Riboflavin under Alkaline Conditions: What Can Gas-Phase Photolysis Tell Us about What Happens in Solution?

Photodegradation of Riboflavin under Alkaline Conditions: What Can Gas-Phase Photolysis Tell Us about What Happens in Solution?

Spectroscopic features of diphenylaryethylenes and arylpolyenes having substituted groups in pairs

Photodegradation of Riboflavin under Alkaline Conditions: What can Gas-Phase Photolysis Tell Us About What Happens in Solution?

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