Solution-and solid-state emitters with large Stokes shifts combining pyrene and 4-hydroxythiazole fluorophores

Wrona-Piotrowicz, Anna; Plażuk, Damian; Zakrzewski, Janusz; Métivier, Rémi; Nakatani, Keitaro; Makal, Anna

doi:10.1016/j.dyepig.2015.05.030

Cited by 14 publications

(3 citation statements)

References 31 publications

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“…[28][29][30][31] We recently reported that a reaction of pyrene with ethoxycarbonylisothiocyanate afforded Nethoxycarbonyl-pyrene-1-carbothioamide in 95% yield. 32 Primary thioamides were obtained in a reaction of electron-rich arenes (1,2-diethoxybenzene, ferrocene) with potassium thiocyanate in methanesulfonic acid. 28,33,34 Herein we report that pyrene reacts with potassium thiocyanate in the presence of 4 equiv.…”

Section: Resultsmentioning

confidence: 99%

Efficient synthesis of pyrene-1-carbothioamides and carboxamides. Tunable solid-state fluorescence of pyrene-1-carboxamides

et al. 2014

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Pyrene reacts with potassium thiocyanate and organic isothiocyanates in the presence of trifluoromethanesulfonic acid to afford primary and secondary pyrene-1-carbothioamides in high yields.These compounds were efficiently oxidatively desulfurized with Oxone® to the corresponding carboxamides. The amides display solid-state fluorescence with quantum efficiencies up to 62%, originating from monomers, aggregates (such as preformed dimers), and/or excimers, depending on the substituent at the nitrogen atom. Single crystal X-ray diffraction characterization of one highly emissive compound supports this assumption.

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Section: Resultsmentioning

confidence: 99%

Efficient synthesis of pyrene-1-carbothioamides and carboxamides. Tunable solid-state fluorescence of pyrene-1-carboxamides

et al. 2014

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“…Data were recorded and histogrammed using the PicoHarp software (Picoquant). For film measurements, a home-built inverted confocal microscope 50 equipped with a tau-SPAD APD (PicoQuant) and the same excitation source and electronics as above was used. Data were fitted by an exponential decay convolved with the instrument response function using a homewritten routine based on the Marquardt least-squares algorithm.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Divalent Tetra- and Penta-phenylcyclopentadienyl Europium and Samarium Sandwich and Half-Sandwich Complexes: Synthesis, Characterization, and Remarkable Luminescence Properties

et al. 2015

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The synthesis of the bulky divalent (polyphenylcyclopentadienyl)lanthanoid sandwich complexes [Ln(C 5 Ph 5 ) 2 ] (Ln = Sm, Eu) and [Ln(C 5 Ph 4 H) 2 (solv)] (Ln = Sm, solv = thf; Ln = Eu, solv = dme)], from redoxtransmetalation/protolysis (RTP) reactions, has been achieved. An analogous reaction with Yb afforded the solvent-separated ion pair [Yb(dme) 4 ][C 5 Ph 4 H] 2 . In addition, rare divalent samarium halide complexes [Sm(C 5 Ph 5 )(μ-Br)(thf) 2 ] 2 and [Sm(C 5 Ph 4 H)I(thf) 3 ], were also prepared, either by RTP or ligand rearrangement. X-ray studies showed that the [Ln(C 5 Ph 5 ) 2 ] complexes adopt highly symmetrical sandwich structures, whereas the [Ln(C 5 Ph 4 H) 2 (solv)] complexes have open sandwich structures. The unexpected, but limited, solubility of the [Ln(C 5 Ph 5 ) 2 ] complexes allowed for variabletemperature NMR spectra of [Sm(C 5 Ph 5 ) 2 ] to be obtained. Detailed 1D and 2D NMR studies were conducted on [Sm(C 5 Ph 4 H) 2 (thf)] to ascertain its structure in donor and nondonor solvents. During the course of these studies, the mixed tetraarylcyclopentadienyl sandwich complex [Sm{C 5 (2,5-Ph) 2 (3,4-p-tol 2 )H} 2 (thf)] was also prepared in order to fully assign the spectrum of [Sm(C 5 Ph 4 H) 2 (thf)]. The europium sandwich complexes [Eu(C 5 Ph 5 ) 2 ] and [Eu(C 5 Ph 4 H) 2 (dme)] exhibit remarkable luminescence properties with high quantum yields (45% and 41%, respectively) coupled w i th long emission lifetimes (approximately 800 and 1300 ns, respectively) in toluene.

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“…Functionalized thioamides containing an ester function at the nitrogen atom are of special interest in this context. Continuing our research program aimed at the development of novel methods of synthesis of thiazoles starting from N -ethoxycarbonyl thioamides, we became interested in the exploration of the synthetic potential of their S -oxides (aminosulfines). Thioamide S -oxides are products of the oxygenation of thioamides .…”

Section: Introductionmentioning

confidence: 99%

Polycyclic Aromatic N-Ethoxycarbonyl Thioamide S-Oxides and Their Triflic Acid Promoted Cyclization to Fluorescent Thiophene Imine-Fused Arenes

et al. 2018

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We present the synthesis of a series of polycyclic aromatic-N-ethoxycarbonylthioamide S-oxides and their triflic acid-promoted cyclization to thiophene imine-fused arenes having 2H-naphtho[1,8-bc]thiophen-2-imine, 3H-pyreno[10,1-bc]thiophen-3-imine, 4H-pyreno[1,10-bc]thiophen-4-imine, 3H-pyreno[10,1-bc]thiophen-3-imine, 4H-pyreno[1,10-bc]thiophen-3-imine, 3H-pyreno[10,1-bc]thiophen-3-imine, and 4H-peryleno[3,4-bc]thiophen-4-imine cores. The proposed reaction mechanism involves the intermediacy of a novel type of electrophilic sulfur species, namely protonated iminosulfenic acid or iminosulfenium cations. These species may attack the peri- or ipso-position of the arene, leading in some cases to regioisomeric products. The reaction affords in high yields novel polycyclic fluorophores emitting in the range of 500-606 nm with quantum yields of 0.025-0.64. Comparison with the parent arenes reveals that the fused iminothiophene moiety brings about significant bathochromic shifts of the absorption and emission bands.

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Solution-and solid-state emitters with large Stokes shifts combining pyrene and 4-hydroxythiazole fluorophores

Cited by 14 publications

References 31 publications

Efficient synthesis of pyrene-1-carbothioamides and carboxamides. Tunable solid-state fluorescence of pyrene-1-carboxamides

Efficient synthesis of pyrene-1-carbothioamides and carboxamides. Tunable solid-state fluorescence of pyrene-1-carboxamides

Divalent Tetra- and Penta-phenylcyclopentadienyl Europium and Samarium Sandwich and Half-Sandwich Complexes: Synthesis, Characterization, and Remarkable Luminescence Properties

Polycyclic Aromatic N-Ethoxycarbonyl Thioamide S-Oxides and Their Triflic Acid Promoted Cyclization to Fluorescent Thiophene Imine-Fused Arenes

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