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Record W2284876855 · doi:10.1021/acs.macromol.5b01372

En Route to Defect-Free Polythiophene Derivatives by Direct Heteroarylation Polymerization

2015· article· en· W2284876855 on OpenAlex

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.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueMacromolecules · 2015
Typearticle
Languageen
FieldMaterials Science
TopicConducting polymers and applications
Canadian institutionsUniversité Laval
FundersNatural Sciences and Engineering Research Council of CanadaKillam Trusts
KeywordsMonomerPolymerizationSubstituentThiopheneChemistrySteric effectsPolymer chemistryCatalysisPolymerBranching (polymer chemistry)Stille reactionCombinatorial chemistryStereochemistryMaterials scienceOrganic chemistry

Abstract

fetched live from OpenAlex

We report the synthesis of well-defined poly(3,3‴-didodecyl-2,2′:5′,2″:5″,2‴-quaterthiophene) (PQT12) from a direct heteroarylation polymerization (DHAP) of 5-bromo-3,3‴-didodecyl-2,2′:5′,2″:5″,2‴-quaterthiophene (monomer A ) and 5-bromo-3′,4″-didodecyl-2,2′:5′,2″:5″,2‴-quaterthiophene (monomer B ). Experiments with different catalysts, ligands, additives, and solvents have revealed that the utilization of Herrmann–Beller catalyst and P( o -NMe 2 Ph) 3 can lead to selective thiophene–thiophene couplings. In this regard, solid-state optical and thermal measurements were particularly useful to detect the presence of β-branching and indicate that minor molecular defects can induce important changes within the supramolecular organization. We also highlight the fact that steric protection around unsubstituted β-positions of α-bromothiophene units is needed to obtain a good selectivity of the cross-couplings at the α-positions. This can be achieved by the presence of a substituent at an adjacent β-position or the utilization of a bulky acidic additive ( i.e ., neodecanoic acid) in the catalytic system. These synthetic procedures applied to both monomers have led to PQT12 samples showing essentially the same optical and thermal properties and are comparable to those observed with their analogues prepared from chemical oxidation or Stille coupling.

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)0.000
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 score0.014
Threshold uncertainty score0.605

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 head0.017
GPT teacher head0.257
Teacher spread0.240 · 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