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Record W2609426384 · doi:10.1021/acs.joc.6b02928

General C–H Arylation Strategy for the Synthesis of Tunable Visible Light-Emitting Benzo[<i>a</i>]imidazo[2,1,5-<i>c</i>,<i>d</i>]indolizine Fluorophores

2017· article· en· W2609426384 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

VenueThe Journal of Organic Chemistry · 2017
Typearticle
Languageen
FieldChemistry
TopicSynthesis and Reactivity of Heterocycles
Canadian institutionsUniversité de MontréalCentre in Green Chemistry and Catalysis
FundersFonds de recherche du Québec – Nature et technologiesUniversité de MontréalNatural Sciences and Engineering Research Council of CanadaCanada Research ChairsCanada Foundation for Innovation
KeywordsChemistryIndolizineSubstituentFluorescenceIntramolecular forceDensity functional theoryAmideTime-dependent density functional theoryElectrophilic substitutionElectrophileCombinatorial chemistryPhotochemistryStereochemistryMedicinal chemistryComputational chemistryOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

Herein we report the discovery of the benzo[ a ]imidazo[2,1,5- c, d ]indolizine motif displaying tunable emission covering most of the visible spectrum. The polycyclic core is obtained from readily available amides via a chemoselective process involving Tf 2 O-mediated amide cyclodehydration, followed by intramolecular C–H arylation. Additionally, these fluorescent heterocycles are easily functionalized using electrophilic reagents, enabling divergent access to varied substitution. The effects of said substitution on the compounds’ photophysical properties were rationalized by density functional theory calculations. For some compounds, emission wavelengths are directly correlated to the substituent’s Hammett constants. Easily introduced nonconjugated reactive functional groups allow the labeling of biomolecules without modification of emissive properties. This work provides a straightforward platform for the synthesis of new moderately bright fluorescent dyes remarkable for their chemical stability, predictability, and unusually high excitation–emission differential.

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)0.001
metaresearch head score (Gemma)0.001
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 score0.007
Threshold uncertainty score0.791

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0010.000
Scholarly communication0.0000.000
Open science0.0020.000
Research integrity0.0000.000
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 head0.021
GPT teacher head0.256
Teacher spread0.235 · 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