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Record W2520978729 · doi:10.1021/acsmacrolett.6b00603

Synthesis of Macrocyclic Poly(3-hexylthiophene) and Poly(3-heptylselenophene) by Alkyne Homocoupling

2016· article· en· W2520978729 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

VenueACS Macro Letters · 2016
Typearticle
Languageen
FieldEngineering
TopicOrganic Electronics and Photovoltaics
Canadian institutionsMcGill UniversityUniversity of Toronto
FundersNatural Sciences and Engineering Research Council of CanadaMinistère de l'Enseignement Supérieur, de la Recherche, de la Science et de la TechnologieUniversity of Toronto
KeywordsAlkynePolymerEthylene glycolMaterials scienceAtom-transfer radical-polymerizationSize-exclusion chromatographyPolymer chemistryMolar mass distributionConjugated systemPolymerizationChemistryOrganic chemistryComposite material

Abstract

fetched live from OpenAlex

Here we report the synthesis of cyclic samples of poly(3-hexylthiophene) (P3HT, degrees of polymerization = 25, 40, and 75) and poly(3-heptylselenophene) (P37S, DP = 30). Cyclization was accomplished using a mild alkyne-alkyne homocoupling procedure. Alkyne-terminated poly(ethylene glycol) was then coupled to residual uncyclized polymers, which were subsequently removed by column chromatography, enabling isolation and characterization of pure cyclic polymers. Cyclization was confirmed by the disappearance of terminal alkyne protons, the decrease in hydrodynamic radius [measured by size exclusion chromatography (SEC)], and the observed identical molecular weight distribution [measured by matrix-assisted laser desorption/ionization (MALDI) mass spectrometry]. The lower weight macrocyclic polymers have decreased self-assembly as measured by optical absorption and transmission electron microscopy. The highest weight macrocycles were imaged using scanning tunneling microscopy. Cyclic polymers adopted a tightly bent conformation, while their linear analogues assembled as fully extended chains. Our method of cyclization and purification is broadly applicable to conjugated polymers (CPs) and will enable the development of novel optoelectronic materials.

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 categoriesMeta-epidemiology (narrow)
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 score0.012
Threshold uncertainty score1.000

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 head0.004
GPT teacher head0.177
Teacher spread0.173 · 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