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Record W2047392898 · doi:10.1021/jo0525938

Synthesis and Characterization of a New Family of Spin Bearing TTF Ligands

2006· article· en· W2047392898 on OpenAlexafffund
M’hamed Chahma, Xiao-shu Wang, Art van der Est, Melanie Pilkington

Bibliographic record

VenueThe Journal of Organic Chemistry · 2006
Typearticle
Languageen
FieldMaterials Science
TopicOrganic and Molecular Conductors Research
Canadian institutionsBrock University
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryCyclic voltammetryTetrathiafulvaleneRadicalElectron paramagnetic resonancePyridinePhotochemistryDiradicalPolymer chemistryMedicinal chemistryOrganic chemistryElectrochemistryMoleculePhysical chemistrySinglet state

Abstract

fetched live from OpenAlex

The syntheses and characterization of two new tetrathiafulvalene (TTF) derivatives bearing pyridine-based substituents and 1,5'-dimethyl-6-oxoverdazyl radicals are described. The TTF-pyridine and bipyridine aldehydes were prepared via a palladium-catalyzed cross-coupling reaction between mono(tributylstannyl)tetrathiafulvalene (3) and the appropriate formylpyridyl halides (4). The radical precursors, the corresponding 1,2,4,5-tetrazanes, were prepared by condensation of the bis(1-methylhydrazide) of carbonic acid with the TTF bearing pyridyl aldehyde. Oxidation of tetrazanes 8 and 9 with 1,4-benzoquinone afforded the donor radicals 1 and 2 as 1:1 complexes with hydroquinone. Both complexes are stable in the solid state and their electronic properties have been characterized by EPR, cyclic voltammetry, and UV/vis spectroscopy. The TTF core of both compounds was oxidized both chemically and electrochemically to afford the corresponding cation diradical species. The electronic properties of both donor radicals have been probed by cyclic voltammetry, UV-vis spectroscopy, and preliminary EPR measurements.

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)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
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 score0.005
Threshold uncertainty score0.423

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
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)0.0000.000

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 head0.013
GPT teacher head0.235
Teacher spread0.222 · 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; a candidate call from one teacher head, not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

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".

Quick stats

Citations40
Published2006
Admission routes2
Has abstractyes

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