Synthesis, absorption and fluorescence properties of N-triazinyl derivatives of 2-aminoanthracene

El‐Sedik, Mervat; Almonasy, Numan; Nepraš, Miloš; Bureš, Filip; Dvořák, Miroslav; Michl, Martin; Čermák, Jan; Hrdina, Radim

doi:10.1016/j.dyepig.2011.08.018

Cited by 19 publications

(13 citation statements)

References 5 publications

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“…Subscripts s and x refer to the standard and the sample of unknown quantum yield, respectively. 52 These F x values indicated that a low number of photons were emitted relative to the number of photons that were deactivated by non-radiative transitions (internal conversion or intersystem crossing), which are favourable if the photons underwent intersystem crossing to the triplet excited state. 51 The emission efficiency in dilute solution largely depends on the molecular structure.…”

Section: Expressed Asmentioning

confidence: 99%

“…The lowest quantum yield (F x = 0.038) was observed for compound 5h possessing electron-withdrawing nitro-substituents at 2-and 4-positions on the 1-phenyl ring. 52 These F x values indicated that a low number of photons were emitted relative to the number of photons that were deactivated by non-radiative transitions (internal conversion or intersystem crossing), which are favourable if the photons underwent intersystem crossing to the triplet excited state. Based on the outcome of fluorescence investigations, quantum yields are not dependent on the properties of electron-donating and withdrawing substituents.…”

Section: Njc Papermentioning

confidence: 99%

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Synthesis, crystal structure, optical and electrochemical properties of novel diphenylether-based formazan derivatives

2015

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In this study, formazans 5a-5h were synthesized by coupling the reactions of substituted phenylhydrazone compounds 3a-3h with diazonium salt of 4-chloro-2-phenoxybenzenamine (4). The substituted phenylhydrazones 3a-3h were obtained from the condensation of substituted phenylhydrazines 1a-1h with 4-methoxybenzaldehyde (2). The structures of the formazans were characterized by using elemental analysis, FTIR, 1 H NMR, 13 C NMR, LC-MS and the crystal structure of compound 5e was determined by X-ray crystallography. The absorption spectra of all compounds were investigated in various solvents. Although their absorption bands are only slightly dependent on the polarities of solvents, the significant change was observed by altering the electronic characteristics of the substituents. The fluorescence quantum yield properties and Stokes shifts of compounds 5a-5h in DMSO were also explored. Electrochemical properties of the new products were studied by CV measurements. In addition, computational studies were conducted at the PBE1PBE/6-311g (2d,2p) level to shed light on the structures of possible tautomers and intramolecular H-bonds.Scheme 1 Synthetic route for the formation of formazan derivatives 5a-5h.Scheme 2 Intramolecular hydrogen bonding and tautomerisation of the formazan system. View Article Onlinea Oxidation and reduction potentials from cyclic voltammograms. b Onsets of oxidation and reduction. c HOMO = À(E onset (ox) + 4.4) (eV), LUMO = À(E onset (red) + 4.4).Scheme 4 (a) Schematic representation of the structure of 5c for possible oxidation mechanisms of 5c, 5d, 5g and 5h; (b) structure of 5a for possible oxidation mechanism of 5a, 5b, 5e and 5f.

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Section: Expressed Asmentioning

confidence: 99%

Section: Njc Papermentioning

confidence: 99%

Synthesis, crystal structure, optical and electrochemical properties of novel diphenylether-based formazan derivatives

2015

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“…The molecules TN1, NTN1, NTN3 and NTN4 absorb experimentally at 265, [38] 274, [43] 381 [44,45] and 348 nm, [45] respectively. From, Figure 2 and Table S2, it is evident that the functionals B3LYP and PBE0 overestimate λ max of TN1, NTN1, NTN3 and NTN4, whereas the functional M06HF underestimates λ max of respective molecules.…”

Section: Absorption Propertiesmentioning

confidence: 99%

“…[42] The synthesis and investigation of spectral features of NTN1 as an ultraviolet (UV)-absorbing molecule were carried out by Wang et al [43] The molecule NTN3 was used in studies of fluorescence quenching. [44] Both NTN3 and NTN4 were probed as trifunctional photoinitiators for source of visible light and UV-LED induced polymerizations. [45] The molecule STN1 was utilized in the examination of Janus head type lone pair-pi-lone pair interactions between the triazine core and halogenated solvents.…”

Section: Introductionmentioning

confidence: 99%

Impact of polycyclic aromatic hydrocarbons and heteroatomic bridges (N, S, and O) on optoelectronic properties of 1,3,5‐triazine derivatives: A computational insight

Vidya

Chetti

2020

J of Physical Organic Chem

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The theoretical investigation of four series of 1,3,5‐triazine derivatives (viz., TN, NTN, STN, and OTN series), which are substituted with polycyclic aromatic hydrocarbons, is carried out by employing density functional theory and time dependent‐density functional theory. The triazine ring acts as electron acceptor (A) and polycyclic aromatic hydrocarbons act as electron donors (D). The aromatic hydrocarbons like benzene, naphthalene (two fused rings), anthracene (three fused rings), and pyrene (four fused rings) are substituted on 1,3,5‐triazine core by means of a bridging heteroatom N, S, and O in the case of NTN, STN, and OTN series of molecules, respectively, whereas polycyclic aromatic hydrocarbons are directly connected to 1,3,5‐triazine in the case of TN series of molecules. The present work aims at examining the impact of number of fused aromatic rings and changing the bridging unit between electron acceptor and electron donor on absorption properties, HOMO‐LUMO gap and first hyperpolarizabilities of molecules under study and provides important insights for architecture of organic molecules for applications in organic optoelectronics.

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“…Beyond their biological properties, various substituted thiazolo [3, 2-a] [1,3,5]triazines were found to have wide applications in industries as dye stuffs, optical bleaches, explosives, in agriculture as pesticides and also to activate the surface of the materials [15,16]. During the past several years, synthesis, UV absorption and fluorescence studies of various substituted N-triazinyl derivatives were investigated [17]. As part our research interest to develop functional organic materials, in this paper, we have reported the three component one pot reaction of indole-3-carbaldehyde Schiff bases, ammonium acetate and p-chloro benzaldehyde to obtain hitherto unreported 4-(4-chlorophenyl)-2-(1H-indol-3-yl)-6-substituted phenyl-2H-thiazolo [3,2-a] [1,3,5]triazines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Fluorescence Properties of Novel indol-3yl-thiazolo[3,2-a][1,3,5]triazines and indole-3-carbaldehyde Schiff Bases

Sravanthi

Manju

2015

J Fluoresc

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Novel photoactive 4-(4-chlorophenyl)-2-(1H-indol-3-yl)-6-substituted phenyl-2H-thiazolo[3,2-a][1,3,5]triazines were synthesized by the conjugate addition of ammonia to the indole-3-carbaldehyde Schiff bases followed by the condensation with 4-chlorobenzaldehyde. All the synthesized compounds were characterized by FT-IR, NMR, mass spectra and elemental analyses. Their antioxidant property, electrochemical and photophysical properties in different organic solvents were investigated. Comparative discussion on the photophysical properties of indole-3-carbaldehyde Schiff bases and 4-(4-chlorophenyl)-2-(1H-indol-3-yl)-6-substituted phenyl-2H-thiazolo[3,2-a][1,3,5]triazines has been described. The fluorescence quantum yield of Schiff bases (Φf = 0.66-0.70 in DMSO) found to be interestingly higher. High fluorescence quantum yield, large molar extinction coefficient, high stokes shift and smaller optical band gap positioning these new derivatives as an efficient metal free organic fluorescent and semiconductor material. Graphical Abstract ᅟ.

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Synthesis, absorption and fluorescence properties of N-triazinyl derivatives of 2-aminoanthracene

Cited by 19 publications

References 5 publications

Synthesis, crystal structure, optical and electrochemical properties of novel diphenylether-based formazan derivatives

Synthesis, crystal structure, optical and electrochemical properties of novel diphenylether-based formazan derivatives

Impact of polycyclic aromatic hydrocarbons and heteroatomic bridges (N, S, and O) on optoelectronic properties of 1,3,5‐triazine derivatives: A computational insight

Synthesis and Fluorescence Properties of Novel indol-3yl-thiazolo[3,2-a][1,3,5]triazines and indole-3-carbaldehyde Schiff Bases

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