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Record W4415667277 · doi:10.1021/acs.joc.5c01700

A Modular and Regioselective Synthesis of Di- and Triarylated Thiophenes: Strategies for Accessing Challenging Isomeric Motifs

2025· article· en· W4415667277 on OpenAlexafffund
Cynthia Messina, Keegan Mckibbon, Philippe Prevost, Vesselin Petkov, Pat Forgione

Bibliographic record

VenueThe Journal of Organic Chemistry · 2025
Typearticle
Languageen
FieldChemistry
TopicSulfur-Based Synthesis Techniques
Canadian institutionsConcordia UniversityCentre in Green Chemistry and CatalysisMAB-Mackay Rehabilitation Centre
FundersFonds de recherche du Québec – Nature et technologiesNatural Sciences and Engineering Research Council of CanadaMitacs
KeywordsModular designRegioselectivitySubstitution (logic)Variety (cybernetics)ArylComponent (thermodynamics)

Abstract

fetched live from OpenAlex

This work demonstrates a highly modular, fully regioselective, and high-yielding route to accessing a variety of multiarylated thiophene motifs. Specifically, this method was used to generate unique diarylated (2,5 or 3,5 or 4,5), triarylated (2,3,5 or 2,4,5 or 3,4,5), and tetra-arylated (2,3,4,5) thiophenes, and branched oligothiophenes. Our approach enables independent introduction of each arene, providing full control over the desired molecular structure. Given that 2,5-aryl-substituted thiophenes are highly sought-after and that aryl substitution at the 3 and 4 positions was previously highly challenging to obtain, our approach represents a facile means to generate these attractive molecules for the next generation of thiophene-based technologies.

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)0.001
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 score0.009
Threshold uncertainty score0.654

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
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)0.0000.000

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 head0.011
GPT teacher head0.252
Teacher spread0.241 · 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

Citations0
Published2025
Admission routes2
Has abstractyes

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