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Record W2111477914 · doi:10.1139/v02-019

The redox properties of ferrocenyl-substituted aryl azines

2002· article· en· W2111477914 on OpenAlex
V.A. Sauro, Mark S. Workentin

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

fundA Canadian funder is recorded on the work.
venuePublished in a venue whose home country is Canada.
no affNo Canadian affiliation: this work is invisible to an affiliation-only frame.
No Canadian affiliation. An affiliation-only frame, the usual design, would never have seen this work. It is one of the works that make the case for inverting the frame.

Bibliographic record

VenueCanadian Journal of Chemistry · 2002
Typearticle
Languageen
FieldChemistry
TopicSynthesis and Biological Evaluation
Canadian institutionsnot available
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryAzineFerrocenePhotochemistryAnthraceneRedoxSubstituentMoietyIsomerizationMedicinal chemistryPyreneElectrochemistryArylCyclic voltammetryPeryleneMoleculeStereochemistryPhysical chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

A series of ferrocenyl substituted azines (1-Fc/Ar, where Ar = 4-NO 2 C 6 H 4 , 4-CNC 6 H 4 , 4-OCH 3 C 6 H 4 , C 5 H 4 N, ferrocene, anthracene, and pyrene) were investigated by electrochemical and photochemical techniques. All the 1-Fc/Ar exhibited oxidation waves within 60 mV of each other, consistent with the expected oxidation of the ferrocene moiety. The reduction properties of 1-Fc/Ar is governed by the nature of the Ar substituent. The standard reduction potentials suggest that ferrocene has comparable electron donating abilities as a 4-methoxyphenyl and 4-dimethyl aminophenyl group. The anthracenyl azines exhibit one-electron reversible reduction followed by dimerization of the radical anion resulting in dimerization rate constants (k d ) between 5.1 × 10 4 and 1.5 × 10 5 M –1 s –1 . 1-Fc/Anth and related azines undergo photochemical E/Z isomerization of the C=N bonds to produce E/Z and Z/Z isomers from the thermodynamically most stable E/E form. Fluorescence at 77 K, was observed for these compounds only after long- wavelength irradiation to produce a mixture of E/E, E/Z, and Z/Z isomers. Fluorescence quantum yields of 0.042, 0.090, and 0.176 were determined for 2-Anth/H, 2-Anth/Anth, and 1-Fc/Anth, respectively. The electrochemical, photochemical, and X-ray data suggest that the azine unit is a conjugation "limiter" and may be a general characteristic of azine molecules.Key words: azines, electrochemistry, cyclic voltammetry, reduction, electron transfer.

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.

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)0.000
metaresearch head score (Gemma)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesInsufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.017
Threshold uncertainty score0.999

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0020.000

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 head0.047
GPT teacher head0.207
Teacher spread0.160 · 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