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Record W2327377103 · doi:10.1021/jo5016085

Donor- and/or Acceptor-Substituted Expanded Radialenes: Theory, Synthesis, and Properties

2014· article· en· W2327377103 on OpenAlexafffund
Sharwatie Ramsaywack, Sıla Karaca, Mojtaba Gholami, Adrian H. Murray, Frank Hampel, Robert McDonald, Nuran Elmacı, Hans Peter Lüthi, Rik R. Tykwinski

Bibliographic record

VenueThe Journal of Organic Chemistry · 2014
Typearticle
Languageen
FieldChemistry
TopicSynthesis and Properties of Aromatic Compounds
Canadian institutionsUniversity of Alberta
FundersNatural Sciences and Engineering Research Council of CanadaDeutsche Forschungsgemeinschaft
KeywordsSonogashira couplingDensity functional theoryConjugated systemTrifluoromethanesulfonateAcceptorComputational chemistryRing (chemistry)Quantum chemicalChemistryPhotochemistryCombinatorial chemistryMaterials scienceMoleculeOrganic chemistryCatalysisPhysicsQuantum mechanicsPalladium

Abstract

fetched live from OpenAlex

The synthesis of donor- (D) and/or acceptor (A)-expanded [4]radialenes has been developed on the basis of readily available dibromoolefin (7), tetraethynylethene (10 and 20), and vinyl triflate (12) building blocks. The successful formation of D/A radialenes relies especially on (1) effective use of a series alkynyl protecting groups, (2) Sonogashira cross-coupling reactions, and (3) the development of ring closing reactions to form the desired macrocyclic products. The expanded [4]radialene products have been investigated by spectroscopic (UV-vis absorption and emission) and quantum chemical computational methods (density functional theory and time dependent DFT). The combined use of theory and experiment provides a basis to evaluate the extent of D/A interactions via the cross-conjugated radialene framework as well as an interpretation of the origin of D/A interactions at an orbital level.

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 machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: none
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.002
Threshold uncertainty score0.007

Distilled classifier scores by category (both heads)

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 communication0.0010.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0020.000

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 head0.204
Teacher spread0.188 · 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 source (direct Gemma or distilled Codex), 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

Citations6
Published2014
Admission routes2
Has abstractyes

Explore more

Same venueThe Journal of Organic ChemistrySame topicSynthesis and Properties of Aromatic CompoundsFrench-language works237,207