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Record W4409618011 · doi:10.1021/acs.joc.4c02321

Phenyldithiafulvene-Substituted Ferrocene Derivatives as Redox-Regulated Molecular Switches

2025· article· en· W4409618011 on OpenAlexafffund
Fatma Takfa, Liam H. Britt, Yuming Zhao

Bibliographic record

VenueThe Journal of Organic Chemistry · 2025
Typearticle
Languageen
FieldChemistry
TopicFerrocene Chemistry and Applications
Canadian institutionsMemorial University of Newfoundland
FundersNatural Sciences and Engineering Research Council of CanadaMemorial University of Newfoundland
KeywordsFerroceneRedoxChemistryMolecular switchCombinatorial chemistryOrganic chemistryElectrochemistryMoleculeElectrode

Abstract

fetched live from OpenAlex

We designed a new type of redox-active molecular triad in which two electron-donating dithiafulvene (DTF) groups are connected to a central ferrocene (Fc) hinge unit through phenylene linkers. Three structural isomers of the (DTF) 2 –Fc system were synthesized through Suzuki–Miyaura cross-coupling followed by phosphite-promoted olefination reactions. The molecular structures and solid-state properties of these compounds were investigated by X-ray single-crystallographic analysis. Their electronic absorption and electrochemical properties in the solution phase were examined using UV–vis spectroscopy and cyclic voltammetry. Our studies showed that these compounds possess multistage redox activities due to the presence of electron-donating DTF and Fc groups, while detailed redox behaviors are dependent on the substitution patterns and steric crowdedness of each compound. To gain deeper insight, we performed density functional theory (DFT) and molecular dynamics (MD) simulations to examine the conformational and electronic properties of these compounds in neutral and different oxidation states. Furthermore, the para -substituted (DTF) 2 –Fc was found to show intriguing supramolecular interactions with γ-cyclodextrin.

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 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 score0.021
Threshold uncertainty score0.998

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0030.000

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 head0.006
GPT teacher head0.237
Teacher spread0.231 · 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.

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

Citations1
Published2025
Admission routes2
Has abstractyes

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