Vibronic singlet and triplet steady-state interplay emissions in phenazine-based 1,2,3-triazole films

Costa, Bárbara B.A.; Souza, Paula D.C.; Gontijo, Rafael N.; Jardim, Guilherme A. M.; Moreira, R. L.; Júnior, Eufrânio N. da Silva; Cury, L. A.

doi:10.1016/j.cplett.2018.02.018

Cited by 6 publications

(4 citation statements)

References 23 publications

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“…Tridimensional forms of these monomers and dimers can be seen in the same previous work [13]. Emissions from the 570 nm to 700 nm wavelength region were associated to the phosphorescent recombination from triplet states [11,12]. This paragraph and the references contained therein are intended to indicate to the reader our rst results, with references to delayed uorescence measurements of the monomer and dimer states of 1,2,3-triazole phenazine molecules, and particularly to the determination of their emissions of phosphorescence and its temporal characteristics.…”

Section: -Results and Discussionsupporting

confidence: 62%

“…The possibility of observing emissions of singlet and triplet levels at room temperature from a single material gave rise to a series of studies made in our group considering their optical properties in steady state [11] and using optical techniques resolved in time [12,13]. In these previous works, blends of 1,2,3triazole phenazine molecules were made in Zeonex (cycloole n polymers -ZEON Corporation), an optically inert and insulating matrix used to disperse and give greater rigidity to the probe's organic molecules.…”

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confidence: 99%

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Multi-conformational Luminescence and Phosphorescence of Few Phenazine 1,2,3-triazole Molecules

et al. 2022

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Dropcast lms produced from blends solutions of phenazine 1,2,3-triazole molecules in very low concentrations in a 1,3-Bis (N-carbazolyl) benzene (mCP) matrix were investigated at room temperature. The mCP acts as an optically inert matrix, having no in uence on the emission properties of the guest molecules. Its conductive properties also ensure that blend lms, within a completely organic character, are formed as truly active layers. The uorescent and phosphorescent emission properties of the phenazine molecules, depending on their conformational states, allowed relatively intense emissions in blue, green, red and also in white, without the need to mix different materials. Although the results of absorption of the blended lms have shown no characteristics of the guest molecules, due to their relatively low concentrations, the excitation of them occurs directly by the incident laser beam. The steady-state spectroscopy for the monomer and dimer singlet uorescence states of respective blue and green emissions of the lms were investigated. The analysis of their temporal decays were done using a different approach based on the Exponentially Modi ed Gaussian (EMG) function. The phosphorescent emissions of the triplet steady-states, occurring in the orange or in the red wavelength regions, were observed to be correlated, respectively, to the formation of guest monomers or to the guest dimers singlet states. I -IntroductionSimple molecular structures of phenazine have been studied since the 1960s [1-5]. Its relatively weak uorescence was mainly due to the decay of its singlet levels to triplet levels via an intersystem crossing (ISC). New phenazine derivative structures with relatively intense uorescent properties have been synthesized and were very useful as probes in a biological environment [6][7][8][9]. In this sense, the 1,2,3triazole phenazine molecule, the same as used in this work, proved to be effective as a selective metal probe, detecting cadmium ions that are extremely harmful to human health [10]. In addition to demonstrate their usefulness as a metal sensor, the 1,2,3-triazole phenazine molecules, also allowed the observation of an intense phosphorescent emission at room temperature.

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Section: -Results and Discussionsupporting

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Multi-conformational Luminescence and Phosphorescence of Few Phenazine 1,2,3-triazole Molecules

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“…The presence of electron-withdrawing groups, on the other hand, is usually followed by an increase in the electronic delocalization of the system. 23 Accordingly, the absorption and fluorescence spectra of molecular structures bearing the nitro group (3l and 3l′) exhibit prominent redshifts, as illustrated in Figure 2. This is illustrated in terms of the emission quantum yields by an inversion of the Φ values, being larger for the 3l′ than that of the 3l solution, contrarily to what was observed for the methoxy group of isomers.…”

Section: ■ Results and Discussionmentioning

confidence: 97%

“…The presence of electron-withdrawing groups, on the other hand, is usually followed by an increase in the electronic delocalization of the system . Accordingly, the absorption and fluorescence spectra of molecular structures bearing the nitro group ( 3l and 3l′ ) exhibit prominent redshifts, as illustrated in Figure .…”

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confidence: 99%

Rhodium(III)-Catalyzed C–H/N–H Alkyne Annulation of Nonsymmetric 2-Aryl (Benz)imidazole Derivatives: Photophysical and Mechanistic Insights

et al. 2020

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Rhodium(III) catalysis enabled C−H/N−H alkyne annulation of nonsymmetric imidazole derivatives. This study encompasses the synthesis of imidazoles from a naturally occurring quinoidal compound and their use for the preparation of rigid πextended imidazole derivatives with outstanding fluorescence. Our study also brings to light the photophysical aspects and the mechanism of the reaction studied via computational calculations. This method provided an efficient and versatile tool for the synthesis of fluorescent compounds with a wide range of chemical and biological applications.

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Ruthenium(II)‐Catalyzed C−H/N−H Alkyne Annulation of Nonsymmetric Imidazoles: Mechanistic Insights by Computation and Photophysical Properties

et al. 2022

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Imidazoles constitute an important class of heterocyclic compounds with extensive potential use, from pharmaceuticals to optoelectronics. However, synthetic methodologies capable of producing novel nonsymmetric imidazoles are still scarce. In a combined synthesis, photophysical and computational investigation, we show that ruthenium(II) catalysis enables C−H/N−H alkyne annulation of nonsymmetric imidazoles derived from naturally occuring β‐lapachone and nor‐β‐lapachone. This method provides an efficient and versatile tool for synthesizing fluorescent compounds with a broad application range.

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Vibronic singlet and triplet steady-state interplay emissions in phenazine-based 1,2,3-triazole films

Cited by 6 publications

References 23 publications

Multi-conformational Luminescence and Phosphorescence of Few Phenazine 1,2,3-triazole Molecules

Multi-conformational Luminescence and Phosphorescence of Few Phenazine 1,2,3-triazole Molecules

Rhodium(III)-Catalyzed C–H/N–H Alkyne Annulation of Nonsymmetric 2-Aryl (Benz)imidazole Derivatives: Photophysical and Mechanistic Insights

Ruthenium(II)‐Catalyzed C−H/N−H Alkyne Annulation of Nonsymmetric Imidazoles: Mechanistic Insights by Computation and Photophysical Properties

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