First Examples of Organophosphorus-Containing Materials for Light-Emitting Diodes

Fave, Claire; Cho, Ting‐Yi; Hissler, Muriel; Chen, Chieh-Wei; Luh, Tien‐Yau; Wu, Chung‐Chih; Réau, Régis

doi:10.1021/ja035155w

Cited by 203 publications

(105 citation statements)

References 30 publications

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“…The other Cu···Au distance is 3.448 , too long to be considered as an interaction. However the gold À gold bonding distances are longer than those in complex 11 a and the range is 3.0633(4)-3.2568 (5) . By comparing both structures we conclude that there are stronger Au···Au interactions and weaker Au···Cu interactions in isomer 11 a than in isomer 11 b.…”

Section: Resultsmentioning

confidence: 73%

“…Luminescent d 10 compounds have received increasing attention over past decades because of their interesting photophysical and photochemical properties and their possible applications in OLED display technology, [1][2][3] as dopant emitters, [4][5][6][7][8] and in sensors for luminescence-based detection of volatile organic compounds. [9][10][11][12] Gold(I) complexes have received considerable attention recently because they exhibit unique features, such as the formation of secondary bonds through aurophilic interactions [13,14] that are similar in strength to hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

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Highly Luminescent Gold(I)–Silver(I) and Gold(I)–Copper(I) Chalcogenide Clusters

Crespo

Gimeno

Laguna

et al. 2006

Chemistry A European J

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The reactions of [AuClL] with Ag2O, where L represents the heterofunctional ligands PPh2py and PPh2CH2CH2py, give the trigoldoxonium complexes [O(AuL)3]BF4. Treatment of these compounds with thio‐ or selenourea affords the triply bridging sulfide or selenide derivatives [E(AuL)3]BF4 (E=S, Se). These trinuclear species react with Ag(OTf) or [Cu(NCMe)4]PF6 to give different results, depending on the phosphine and the metal. The reactions of [E(AuPPh2py)3]BF4 with silver or copper salts give [E(AuPPh2py)3M]2+ (E=O, S, Se; M=Ag, Cu) clusters that are highly luminescent. The silver complexes consist of tetrahedral Au3Ag clusters further bonded to another unit through aurophilic interactions, whereas in the copper species two coordination isomers with different metallophilic interactions were found. The first is analogous to the silver complexes and in the second, two [S(AuPPh2py)3]+ units bridge two copper atoms through one pyridine group in each unit. The reactions of [E(AuPPh2CH2CH2py)3]BF4 with silver and copper salts give complexes with [E(AuPPh2CH2CH2py)3M]2+ stoichiometry (E=O, S, Se; M=Ag, Cu) with the metal bonded to the three nitrogen atoms in the absence of Au⋅⋅⋅M interactions. The luminescence of these clusters has been studied by varying the chalcogenide, the heterofunctional ligand, and the metal.

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Section: Resultsmentioning

confidence: 73%

Section: Introductionmentioning

confidence: 99%

Highly Luminescent Gold(I)–Silver(I) and Gold(I)–Copper(I) Chalcogenide Clusters

Crespo

Gimeno

Laguna

et al. 2006

Chemistry A European J

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“…1), which is stable at room temperature. The phosphorus atom behaves as a classical 2-electron donor toward the gold(I) atom (18). The simplicity of the 13 C NMR spectra recorded in solution is in favor of a symmetric structure.…”

Section: Resultsmentioning

confidence: 99%

“…GoPI Synthesis-The synthesis of [1-phenyl-2,5-di(2-pyridyl)-phosphole}AuCl] was carried out in analogy to the synthesis of [{1-phenyl-2,5-di(2-thienyl)phosphole}AuCl] (18,19) and [{1-phenyl-2,5-di(2-pyridyl)phosphole}W(CO) 5 ] (20). The reactant 1-phenyl-2,5-di(2-pyridyl)phosphole was synthesized as described previously (16).…”

Section: Methodsmentioning

confidence: 99%

Mechanistic Studies on a Novel, Highly Potent Gold-Phosphole Inhibitor of Human Glutathione Reductase

Deponte

Urig

Arscott

et al. 2005

Journal of Biological Chemistry

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The homodimeric flavoprotein glutathione reductase (GR) is a central player of cellular redox metabolism, connecting NADPH to the large pool of redox-active thiols. In this work, the inhibition of human GR by a novel gold-phosphole inhibitor (GoPI) has been studied in vitro. Two modes of inhibition are observed, reversible inhibition that is competitive with GSSG followed by irreversible inhibition. When ϳ1 nM GoPI is incubated with NADPH-reduced GR (1.4 nM) the enzyme becomes 50% inhibited. This appears to be the most potent stable inhibitor of human GR to date. Analyzing the monophasic oxidative half-reaction of reduced GR with GSSG at pH 6.9 revealed a

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“…Réau and coworkers prepared and evaluated the photophysical and electrochemical properties of a series of phosphole derivatives. [19][20][21][22][23][24][25] These authors made several structural variations for tuning the electronic and optical properties and the thermal stability of the phosphole-containing -conjugated oligomers. One approach is that the substituents, such as phenyl and thienyl, were introduced at the 2,5-positions of the P-ring.…”

Section: Introductionmentioning

confidence: 99%

Structural, electronic, and optical properties of phosphole‐containing π‐conjugated oligomers for light‐emitting diodes

2007

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The purpose of this work is to provide an in-depth interpretation of the optical and electronic properties of a series of phosphole derivatives, including 2,5-diphenylthiooxophosphole (2a), 2-phenyl-5-biphenylthiooxophosphole (3a), 2-phenyl-5-stilbenylthiooxophosphole (4a), 2,5-dithienylthiooxophosphole (2b), 2-thienyl-5-biphenylthiooxophosphole (3b), 2-thienyl-5-stilbenylthiooxophosphole (4b), and dibenzophosphole 1. These thiooxophospholes show great potential for application in OLEDs as efficient red emitters due to the tuning of the optical and electronic properties by the use of various substituents at the 2,5-positions of the phosphole ring. The geometric and electronic structures of the oligomers in the ground state were investigated using density functional theory (DFT) and the ab initio HF, whereas the lowest singlet excited states were optimized with ab initio CIS. To assign the absorption and emission peaks observed in the experiment, we computed the energies of the lowest singlet excited states with time-dependent DFT (TD-DFT). All DFT calculations were performed using the B3LYP functional and the 6-31G (d) basis set. The results show that the HOMOs, LUMOs, energy gaps, ionization potentials, and electron affinities for the phosphole derivatives are significantly affected by varying the phosphole ring substituents at the 2,5-positions, which favor the hole and electron injection into OLEDs. The absorption and emission spectra exhibit red shifts to some extent [the absorption spectra: 339.63 (1)<358.65 (2a)<373.77 (3a)<443.89 nm (4a) and 403.03 (3b)<449.11 (2b)<460.19 nm (4b); the emission spectra: 418.42 (1)<513.62 (2a)<556.51 (3a)<642.59 nm (4a) and 568.31 (2b)<631.11 (3b)<647.35 nm (4b)] and the Stokes shifts are unexpectedly large ranging from 78 to 228 nm resulting from a more planar conformation of the excited state for the phosphole derivatives.

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First Examples of Organophosphorus-Containing Materials for Light-Emitting Diodes

Cited by 203 publications

References 30 publications

Highly Luminescent Gold(I)–Silver(I) and Gold(I)–Copper(I) Chalcogenide Clusters

Highly Luminescent Gold(I)–Silver(I) and Gold(I)–Copper(I) Chalcogenide Clusters

Mechanistic Studies on a Novel, Highly Potent Gold-Phosphole Inhibitor of Human Glutathione Reductase

Structural, electronic, and optical properties of phosphole‐containing π‐conjugated oligomers for light‐emitting diodes

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