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Record W2121863825 · doi:10.1002/chem.201302452

Synthesis and Derivatization of Expanded [<i>n</i>]Radialenes (<i>n</i>=3, 4)

2013· article· en· W2121863825 on OpenAlexafffund
Mojtaba Gholami, Sharwatie Ramsaywack, Manuel N. Chaur, Adrian H. Murray, Robert McDonald, Michael J. Ferguson, Luís Echegoyen, Rik R. Tykwinski

Bibliographic record

VenueChemistry - A European Journal · 2013
Typearticle
Languageen
FieldChemistry
TopicSynthesis and Properties of Aromatic Compounds
Canadian institutionsUniversity of Alberta
FundersNatural Sciences and Engineering Research Council of CanadaWelch FoundationUniversidad del ValleNational Science Foundation
KeywordsSonogashira couplingRing (chemistry)DerivatizationAcceptorSurface modificationCombinatorial chemistryElectrochemistryChemistryMaterials scienceCrystallographyPalladiumOrganic chemistryCatalysisPhysical chemistryPhysics

Abstract

fetched live from OpenAlex

Versatile, iterative synthetic protocols to form expanded [n]radialenes have been developed (n=3 and 4), which allow for a variety of groups to be placed around the periphery of the macrocyclic framework. The successful use of the Sonogashira cross-coupling reaction to complete the final ring closure demonstrates the ability of this reaction to tolerate significant ring strain while producing moderate to excellent product yields. The resulting radialenes show good stability under normal laboratory conditions in spite of their strained, cyclic structures. The physical and electronic characteristics of the macrocycles have been documented by UV-visible spectroscopy, electrochemical methods, and X-ray crystallography (four derivatives), and these studies provide insight into the properties of these compounds as a function of pendent substitution in terms of conjugation and donor/acceptor functionalization.

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 score0.065
Threshold uncertainty score0.996

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)0.0050.000

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 head0.012
GPT teacher head0.184
Teacher spread0.172 · 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

Citations11
Published2013
Admission routes2
Has abstractyes

Explore more

Same venueChemistry - A European JournalSame topicSynthesis and Properties of Aromatic CompoundsFrench-language works237,207