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Record W4367173573 · doi:10.1002/ejoc.202300284

Dihydroazulene‐Boron Subphthalocyanine Conjugates with Oligo(phenyleneethynylene) Bridging Unit: Photoswitchable Fluorophores

2023· article· en· W4367173573 on OpenAlexafffund
Esmeralda Bukuroshi, Anne Ugleholdt Petersen, Cecilie Jensen, Mathias Kirkholt Lund, Martin Kühnel, Kasper Nørgaard, Timothy P. Bender, Mogens Brøndsted Nielsen

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2023
Typearticle
Languageen
FieldMaterials Science
TopicPorphyrin and Phthalocyanine Chemistry
Canadian institutionsUniversity of Toronto
FundersNatural Sciences and Engineering Research Council of CanadaMitacsUniversity of Toronto
KeywordsChemistryBridging (networking)BoronConjugatePhotochemistryPolymer chemistryCombinatorial chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

Abstract In this work, we have linked the dihydroazulene (DHA)/vinylheptafulvene (VHF) photo‐/thermoswitch and the boron subphthalocyanine (BsubPc) fluorophore via an axial oligo(phenyleneethynylene) bridging unit into new DHA‐BsubPc conjugates. The objectives were to elucidate the influence of BsubPc on the DHA/VHF switching reactions and the influence of DHA/VHF on the BsubPc fluorescence in these conjugates for which the entire axial substituent connected to boron comprises one large, conjugated scaffold. We present the synthesis and properties of DHA‐BsubPc conjugates with varying peripheral substituents on the BsubPc core, being either unsubstituted (H12BsubPc) or partially fluorinated (F6BsubPc). Fluorination of the BsubPc core provided a remarkable increase in the reversibility of the DHA‐VHF interconversions promoted by light and heat, respectively, and accompanied by on/off switching of the BsubPc fluorescence. Synthetically, the units were connected using Sonogashira coupling reactions of suitable acetylenic building blocks.

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: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.001
Threshold uncertainty score0.004

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 communication0.0000.000
Open science0.0000.000
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 head0.013
GPT teacher head0.214
Teacher spread0.201 · 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

Citations3
Published2023
Admission routes2
Has abstractyes

Explore more

Same venueEuropean Journal of Organic ChemistrySame topicPorphyrin and Phthalocyanine ChemistryFrench-language works237,207