Phototransposition chemistry of 1-phenylpyrazole. Experimental and computational studies

Pavlik, James W.; Connors, Robert E.; Burns, Douglas S.; Kurzweil, Edyth M.

doi:10.1021/ja00070a008

Cited by 36 publications

(23 citation statements)

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“…[50] It has become one of the most popular cyclometalating ligands for iridium. The result of ppz incorporation translates into a blueshift in the emission spectrum, which is mainly due to a destabilization of the π* orbitals of the ppz ligand relative to ppy, as Pavlik and Connors et al had demonstrated years before.…”

Section: -Arylpyrazole (Ppz; 26a-c) and 2-(1h-pyrazol-1-yl)pyridine mentioning

confidence: 99%

“…The bpy‐based complexes with 1‐phenylpyrazole (ppz; 26a ) C∧N ligands possess a larger HOMO–LUMO gap than their homologous ppy complexes. The result of ppz incorporation translates into a blueshift in the emission spectrum, which is mainly due to a destabilization of the π* orbitals of the ppz ligand relative to ppy, as Pavlik and Connors et al had demonstrated years before 50. It has become one of the most popular cyclometalating ligands for iridium.…”

Section: The Photophysics Of [(Ppy)2ir(bpy)]+mentioning

confidence: 99%

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A Comprehensive Survey of Cationic Iridium(III) Complexes Bearing Nontraditional Ligand Chelation Motifs

2013

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The useful optoelectronic properties of cationic iridium(III) complexes have been exploited in diverse applications, from visual displays to biological probes to analytical sensors. It is thus not surprising to note the increased recent efforts to document, understand, and ultimately control the photophysical and electrochemical properties of the archetypal cationic iridium(III) complex [(ppy) 2 Ir(bpy)] + , in which ppyH = 2phenylpyridine and bpy = 2,2Ј-bipyridine, and decorated versions thereof. Of the ligand architectures explored, the [a] Département 2986with N-heterocyclic carbenes (NHCs) are also included within the survey. We also wish to direct the reader to other recent review articles on other facets of Ir III chemistry, property evaluation, and applications. [1] This Review commences with a historical overview of iridium(III) chemistry, an account of the properties of iridium, and a comprehensive description of the photophysical properties of [(ppy) 2 Ir(bpy)] + (1), supported by a detailed DFT study. Following this perspective, the survey is then organized by type of heterocycle. The properties of these complexes are compared and contrasted with the archetype complex 1 and fluorinated congener [(dFppy) 2 Ir(bpy)] + (2), which in this Review act as benchmarks. Finally, optoelectronic data from complexes with structurally similar ligands are collated together to elucidate more clearly the salient structure-property relationships.

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Section: -Arylpyrazole (Ppz; 26a-c) and 2-(1h-pyrazol-1-yl)pyridine mentioning

confidence: 99%

Section: The Photophysics Of [(Ppy)2ir(bpy)]+mentioning

confidence: 99%

A Comprehensive Survey of Cationic Iridium(III) Complexes Bearing Nontraditional Ligand Chelation Motifs

2013

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“…One such modifi cation involves replacing the pyridyl of ppy with a pyrazolyl group, i.e., Ir(ppz) 3 , Scheme 3.3 . The emission energy of fac -Ir(ppz) 3 ( λ max = 414 nm, 77 K) is signifi cantly greater than that of fac -Ir(ppy) 3 [121] is much higher than that of ppyH (vida supra). Unfortunately, no detectable emission from fac -Ir(ppz) 3 is observed at room temperature, in fl uid or solid solutions [57,122] .…”

Section: Near -Uv Luminescent Cyclometallated Complexesmentioning

confidence: 96%

Cyclometallated Organoiridium Complexes as Emitters in Electrophosphorescent Devices

Djurovich

Thompson

2007

Highly Efficient OLEDs With Phosphorescent Materials

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A brief overview is presented on cyclometallated iridium complexes that are used as phosphorescent dopants in organic light -emitting devices (OLEDs). Comparisons between devices made using either Pt(octaethylporphyrin) or Ir(phenylpyridyl) 3 as dopants are used to illustrate some parameters needed for optimal performance of electrophosphorescent OLEDs. The molecular properties responsible for the high luminescent effi ciency of the Ir complexes are then described. Interactions between the triplet ligand state and the singlet and triplet metal -to -land charge transfer states are responsible for photophysical characteristics of the complexes. Examples are given of various ligand combinations used to control the phosphorescent energy and effi ciency. This knowledge enables one to systematically tune the emission colors of these complexes from the near -UV to the near -infrared spectral regions. Organic Light -Emitting DevicesThe future holds tremendous opportunity for the low cost and high performance offered by organic LEDs. The term organic light -emitting device (OLED) refers to any light -emitting diode that is composed of either molecular or polymeric materials. Full -color displays that use OLEDs may eventually replace liquid -crystal displays (LCDs) in a range of mobile applications, ranging from cellular phones to laptop computers. The low power dissipation and high brightness of OLEDs make them ideal for such portable applications. OLED displays can be deposited on fl exible plastic or metal foils, eliminating the fragile and heavy glass substrates used in LCDs and other fl at panel displays. Moreover, OLED displays emit light without the pronounced directionality inherent in LCD viewing, all with effi ciencies signifi cantly higher than typical LCD panels. It is possible that portable and lightweight roll -up OLED displays will someday cover our walls. Another important application for OLEDs is in illumination. The high effi ciencies and excellent color qualities for white OLEDs make them promising candidates for replacing conventional fl uorescent and incandescent light sources.

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“…A sample of 475 mg (3.0 mmol) of 5-methyl-1-phenylpyrazole 54 was first dissolved in 2 mL of anhydrous CHCl 3 and then treated with 0.4 mL (6.0 mmol) of chlorosulfonic acid. The resulting mixture was then heated at reflux temperature over a period of 2 h. After cooling, the mixture was concentrated in vacuo and poured on 100 mL of ice.…”

Section: -Methyl-1-phenylpyrazole-4-sulfonic Acid (17)mentioning

confidence: 99%

Pyrazolium-sulfonates. Mesomeric betaines possessing iminium-sulfonate partial structures

Dreger¹,

Münster²,

Nieto‐Ortega³

et al. 2011

Arkivoc

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Pyrazolium-3-sulfonates and pyrazolium-4-sulfonates possessing the iminiomethanesulfonate and the 3-iminio-pro-1-ene-2-sulfonate partial structure are prepared. Formally, they represent sulfur analogs of cross-conjugated (CCMB) and pseudo-cross-conjugated heterocyclic mesomeric betaines (PCCMB) and sulfur trioxide adducts of abnormal N-heterocyclic carbenes (aNHC) and N-heterocyclic carbenes (NHC), respectively. The theoretical as well as experimental vibrational spectra of these two classes are compared. Results of calculations of HOMO/LUMO profiles and an X-ray single crystal structure analysis are presented.

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Phototransposition chemistry of 1-phenylpyrazole. Experimental and computational studies

Cited by 36 publications

References 0 publications

A Comprehensive Survey of Cationic Iridium(III) Complexes Bearing Nontraditional Ligand Chelation Motifs

A Comprehensive Survey of Cationic Iridium(III) Complexes Bearing Nontraditional Ligand Chelation Motifs

Cyclometallated Organoiridium Complexes as Emitters in Electrophosphorescent Devices

Pyrazolium-sulfonates. Mesomeric betaines possessing iminium-sulfonate partial structures

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