Absorption and fluorescent spectral studies of imidazophenazine derivatives

Ryazanova, Olga; Zozulya, Victor; Voloshin, Igor; Karachevtsev, V. A.; Makitruk, V. L.; Stepanian, S. G.

doi:10.1016/j.saa.2003.10.020

Cited by 12 publications

(14 citation statements)

References 12 publications

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“…In further discussion of the results, it is necessary to establish whether the reduction of the compounds under study can proceed in glycerol without FAB influence. Earlier obtained fluorescent spectroscopic data5 are of help here and give a definite negative answer to the question. The spectroscopic data provide evidence of the formation of hydrogen bonds between the dyes and the glycerol molecules, but give no sign of the hydrogen attachment to the dye molecules.…”

Section: Resultsmentioning

confidence: 91%

“…It is interesting to look for some correlations between the distinct structural features of the compounds I – V and the differences in the distribution of the intensities in their [M + n H] + peak groups. Purely empirical considerations concerning the effect of different functional groups5 are of little help here, except in the case of compound II where addition of one more nitrogen increases the number of the protonation sites. Such experimentally determined parameters as electrochemical reduction potentials are presently unavailable for the imidazophenazine derivatives under study.…”

Section: Resultsmentioning

confidence: 99%

“…Clearly, the orbitals are distributed over almost all atoms of the tetracyclic conjugated system with the exception of the H‐ and ribose‐substituted N atom in the imidazole ring. In compounds ( II ) and ( IV ), the extra N atom and the CF 3 substituent5 affects the LUMO localization. In the ribo‐imidazophenazine ( V ) molecule, the LUMO and the HOMO do not extend to the sugar moiety.…”

Section: Resultsmentioning

confidence: 99%

“…In the framework of our current studies of a series of dyes—derivatives of imidazophenazine—by various experimental techniques,5 mass‐spectral characterization of the dyes by means of the FAB technique has been made. It revealed the appearance of the peaks of the [M + 2] +• and [M + 3] + type in the group of peaks of their respective native molecular ions.…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of the reduction of imidazophenazine dye derivatives under fast‐atom‐bombardment mass‐spectrometric conditions

et al. 2005

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Satellite [M + 2](+*) and [M + 3](+) peaks accompanying the common peak of the protonated molecule [M + H](+) that are known to indicate the occurrence of a reduction process were observed in the fast atom bombardment (FAB) mass spectra of imidazophenazine dye derivatives in glycerol matrix. The distribution of the abundances in the [M + nH](+) peak group varied noticeably for different derivatives. This indicated different levels of the reduction depending on the different structure variations of the studied molecules. In the search for correlations between the mass spectral pattern and the structural features of the dyes, ab initio HF/6-31++G** quantum chemical calculations were performed. They revealed that the abundances of the [M + 2](+*) and [M + 3](+) ions show growth proportional to the decrease of the energy of the lowest unoccupied molecular orbital, i.e. proportional to the increase of the electron affinity of the dye molecule. A method for rapid screening of reductive properties of sets of dye derivatives on the basis of the FAB mass spectral data is discussed.

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Section: Resultsmentioning

confidence: 91%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Evaluation of the reduction of imidazophenazine dye derivatives under fast‐atom‐bombardment mass‐spectrometric conditions

et al. 2005

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“…[36] In the presents tudy,w ec ompare the interaction of the following chromophores:i midazo-[4,5-d]-phenazine (F1)a nd its derivatives (2-methylimidazo-[4,5-d]-phenazine (F2), 2-trifluoromethylimidazo-[4,5-d]-phenazine( F3), and 1,2,3-triazole-[4,5-d]phenazine (F4)( Figure 1) with graphene. Note that these compounds are very perspective in DNA structure studies, [37][38][39][40] and the fluorescences tudy of these dyes [41] shows pH sensitivity of their spectralp roperties. Pre-resonance Raman and IR absorption spectroscopy techniques were applied to study the influence of substitutes in the imidazole ring of F1 on its vibrational structure.…”

Section: Introductionmentioning

confidence: 99%

Noncovalent Interaction of Graphene with Heterocyclic Compounds: Benzene, Imidazole, Tetracene, and Imidazophenazines

et al. 2016

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Noncovalent functionalization of graphene with organic molecules offers a direct route to multifunctional modification of this nanomaterial, leading to its various possible practical applications. In this work, the structures of hybrids formed by linear heterocyclic compounds such as imidazophenazine (F1) and its derivatives (F2-F4) with graphene and the corresponding interaction energies are studied by using the DFT method. Special attention is paid to the hybrids where the attached molecule is located along the graphene zigzag (GZZ ) and armchair (GAC ) directions. The interaction energies corresponding to the graphene hybrids of the F1-F4 compounds for the two directions are found to be distinct, while tetracene (being a symmetrical molecule) shows a small difference between these binding energies. It is found that the back-side CH3 and CF3 groups have an important influence on the arrangements of F1 derivatives on graphene and on their binding energies. The contribution of the CF3 group to the total binding energy of the F3 molecule with graphene is the largest (3.4 kcal mol(-1) ) (the GZZ direction) while the CH3 group increases this energy of F2 only by 2.0 kcal mol(-1) (the GAC direction). It is shown that replacing the carbons with other atoms or adding a back-side group enables one to vary the polarizability of graphene.

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Study on the synthesis and structure–effect relationship of multi‐aryl imidazoles with their fluorescence properties

Tian

Wang

et al. 2013

Luminescence

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In this paper, 23 multi-aryl imidazole derivatives were synthesized and identified by nuclear magnetic resonance, ultraviolet-visible and elemental analysis. At the same time, their ultraviolet-visible maximum absorption (λ(ab)(max)), fluorescence emission maximum (λ(em)(max)) and quantum yields (Ф(f)) were measured. The relationships between the optical behaviors and structures for these compounds were assessed. The results show that the λ(max)(ab) and λ(max)(em) are red-shifted and the fluorescence Ф(f) are increased by the introduction of electron-withdrawing substituents and the increase in the planarity of multi-aryl imidazole molecules. The results also showed that the fluorescence quantum yields of the compounds containing two imidazole nuclei are double the corresponding mono-imidazole nucleus compounds.

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Absorption and fluorescent spectral studies of imidazophenazine derivatives

Cited by 12 publications

References 12 publications

Evaluation of the reduction of imidazophenazine dye derivatives under fast‐atom‐bombardment mass‐spectrometric conditions

Evaluation of the reduction of imidazophenazine dye derivatives under fast‐atom‐bombardment mass‐spectrometric conditions

Noncovalent Interaction of Graphene with Heterocyclic Compounds: Benzene, Imidazole, Tetracene, and Imidazophenazines

Study on the synthesis and structure–effect relationship of multi‐aryl imidazoles with their fluorescence properties

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