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Record W1492443668 · doi:10.1002/ejoc.201300230

Direct Synthesis of 2,5‐Bis(dodecanoxy)phenyleneethynylene‐Butadiynes by Sonogashira Coupling Reaction

2013· article· en· W1492443668 on OpenAlexaff
Eduardo Arias, Ivana Moggio, Ronald F. Ziolo, José‐Luis Maldonado, Kirk Green, Thomas M. Cooper, Geoffrey Wicks, Aleksander Rebane, Mikhail Drobizhev, Nikolay S. Makarov, Massimo Ottonelli, G. Dellepiane

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2013
Typearticle
Languageen
FieldMaterials Science
TopicPorphyrin and Phthalocyanine Chemistry
Canadian institutionsMcMaster University
FundersAir Force Office of Scientific ResearchU.S. Air Force
KeywordsSonogashira couplingChemistryIntersystem crossingPhotochemistryDimerHeck reactionChromophoreCoupling reactionFluorescenceSinglet stateExcited statePalladiumOrganic chemistry

Abstract

fetched live from OpenAlex

Abstract The synthesis of a 2,5‐bis(dodecanoxy)phenyleneethynylene‐butadiyne series with 2, 4, 6 and 8 phenyl rings is reported. Sonogashira coupling reaction, rather than the Glaser/Eglinton/Hay reactions classically used for butadiyne formation was applied. The molecular structures of all compounds were confirmed by 1H, DEPT‐135, APT 13C, MALDI‐TOF, FTIR and FT‐Raman analyses. The linear and nonlinear optical properties were studied in solution by UV/Vis, static and time‐resolved fluorescence, and by two‐photon absorption (2PA) spectroscopy. With the exception of the dimer, for which intersystem crossing is very favoured due to the low energy gap between the singlet and triplet states as theoretically predicted, the other oligomers present high fluorescence quantum yields (0.77–0.82) and large cross‐sections (up to 5000 GM for the octamer) that could be applied in multiphoton microscopy or nonlinear optics.

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 score0.002
Threshold uncertainty score0.005

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)0.0020.001

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 head0.008
GPT teacher head0.197
Teacher spread0.189 · 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

Citations8
Published2013
Admission routes1
Has abstractyes

Explore more

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