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Record W2098122446 · doi:10.1002/047084289x.rn01759

Iridium, Tris[2-(2-pyridinyl-κ<i>N</i>)phenyl-κ<i>C</i>]-, (OC-6-22)-iridium

2015· reference-entry· en· W2098122446 on OpenAlexaff
Anne‐Catherine Bédard, Shawn K. Collins

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2015
Typereference-entry
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsUniversité de Montréal
Fundersnot available
KeywordsIridiumChemistryAcetonitrileToluenePyridineFerroceneSolubilityTrisNuclear chemistryDichloromethaneProton NMRPhenylboronic acidMedicinal chemistryCatalysisSolventStereochemistryOrganic chemistryPhysical chemistryElectrochemistry

Abstract

fetched live from OpenAlex

[94928-86-6] C33H24IrN3 (MW: 654.78) InChI = 1S/3C11H8N.Ir/c3*1-2-6-10(7-3-1)11-8-4-5-9-12-11;/h3*1-6,8-9H; InChIKey = QKBWDYLFYVXTGE-UHFFFAOYSA-N (photosensitizer, photoredox catalysis, OLED, triplet-state luminescence) Alternative Names: Ir(ppy)3, tris[2-phenylpyridinato-C2,N]iridium(III). Physical Data: UV (ϵ [×103 M−1cm−1]) in DCM = 283 (4.9), 380 (4.1), 405 (4.0), 455 (3.5), 490 (3.1)1, 2; λem = 516 nm in DCM; E1/2 Red = (2.77 V; E1/2 Ox 0.26 V (in THF or DCM, respectively, Ref. vs. ferrocene)3; E1/2 Red = (1.73 V vs. SCE4; mp 328 °C. Solubility: acetonitrile, dichloromethane, THF, ethyl acetate, toluene, and DMF. Form Supplied in: commercially available. Complex is a yellow solid. Preparation Methods: prepared from the reaction of Ir(acac)3 with 3 equiv of H–ppy in degassed glycerol at reflux for 10 h, followed by precipitation with 1 M HCl (eq 1).5 Alternatively, reaction of cis-[Ir(ppy)2(H2O)2]OTf6 and 2-(2-boronic acid phenyl)pyridine under basic conditions at room temperature has been reported 7 (1) NMR data in the literature reports the 1H NMR spectra for the title compound in CD2Cl2 as showing eight chemical shifts in the range of 6.7–8.0 ppm, and the 13C NMR spectrum showing 11 resonances, 3 of which remain unsplit in SFORD measurements.8 Purification: silica gel chromatography in DCM to remove dark colored impurities.9 Handling, Storage, and Precaution: store under inert atmosphere in the dark (sensitive to light). Keep away from oxidizing agents. Upon visible light excitation of Ir(ppy)3 (ppy = 2-phenyl pyridine), the resulting metal-to-ligand charge transfer (MLCT) excited-state species [Ir(ppy)3]* is a strong single-electron reductant and can be quenched with an acceptor to form [Ir(ppy)3+]. The oxidized species can be reduced back by an electron donor to regenerate the photocatalyst (eq 2). (2) The complex is also used as an organic light-emitting diode (OLED)10-14 and an oxygen sensor.15, 16

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.007
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Research integrity, Insufficient payload (model declined to judge)
Consensus categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: Not applicable
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.124
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.007
Meta-epidemiology (narrow)0.0020.002
Meta-epidemiology (broad)0.0030.001
Bibliometrics0.0010.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0020.001
Research integrity0.0020.001
Insufficient payload (model declined to judge)0.0150.001

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.024
GPT teacher head0.272
Teacher spread0.249 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; both teacher heads agree on what is shown here.

Study designNot applicable
Domainnot available
GenreOther

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

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Citations0
Published2015
Admission routes1
Has abstractyes

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