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Record W4408457996 · doi:10.1002/cptc.202500042

Double Click for Chirality: Chiral Dibenzo‐cycloocta‐bis‐triazoles via Strain‐Promoted Alkyne‐Azide Cycloaddition

2025· article· en· W4408457996 on OpenAlexaff
Sebastian Pim, Aaron D. G. Campbell, Dmitry Levshov, Wouter Herrebout, Michael J. Hall, Roly J. Armstrong, Donal F. O’Shea

Bibliographic record

VenueChemPhotoChem · 2025
Typearticle
Languageen
FieldChemistry
TopicClick Chemistry and Applications
Canadian institutionsSt. Stephen's University
FundersScience Foundation Ireland
KeywordsCycloadditionChirality (physics)AzideAlkyneChemistryStrain (injury)Click chemistryStereochemistryCombinatorial chemistryCatalysisOrganic chemistryPhysicsSymmetry breakingChiral symmetry breakingBiologyParticle physics

Abstract

fetched live from OpenAlex

Abstract The synthetically convenient strain promoted double azide cycloaddition of the Sondheimer‐Wong diyne produces resolvable chiral dibenzo‐cycloocta‐bis‐triazoles whose stereogenicity, to date, has gone unrecognised. Enantiomers were separable by chiral HPLC and showed no racemization at 100 °C. This unique method to produce chiral substrates was exploited for the synthesis and resolution of a chiral fluorescent BF 2 ‐azadipyrromethene, with absorption and emission spanning the important spectral range of 600 to 700 nm. The fluorophore properties were studied utilising X‐ray structural analysis, electronic circular dichroism spectra and DFT calculations.

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 categoriesMeta-epidemiology (narrow), Insufficient 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 score0.087
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0010.000
Insufficient payload (model declined to judge)0.0010.000

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 head0.018
GPT teacher head0.298
Teacher spread0.280 · 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

Citations2
Published2025
Admission routes1
Has abstractyes

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