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Record W2738060849 · doi:10.1002/chem.201702597

Testing the Limits of the BOPHY Platform: Preparation, Characterization, and Theoretical Modeling of BOPHYs and Organometallic BOPHYs with Electron‐Withdrawing Groups at β‐Pyrrolic and Bridging Positions

2017· article· en· W2738060849 on OpenAlexafffund
Yuriy V. Zatsikha, Dion B. Nemez, Rebecca L. Davis, Simarpreet Singh, David E. Herbert, Alexander King, Christopher J. Ziegler, Victor N. Nemykin

Bibliographic record

VenueChemistry - A European Journal · 2017
Typearticle
Languageen
FieldMaterials Science
TopicLuminescence and Fluorescent Materials
Canadian institutionsUniversity of Manitoba
FundersCanadian Network for Research and Innovation in Machining Technology, Natural Sciences and Engineering Research Council of CanadaCanada Foundation for Innovation
KeywordsChemistryDifferential pulse voltammetryAdductCyclic voltammetryFerroceneElectrochemistryPhotochemistryCrystallographyPhysical chemistryOrganic chemistryElectrode

Abstract

fetched live from OpenAlex

Abstract Several BOPHY derivatives with and without ferrocene fragments, and with electron‐withdrawing ester groups appended to the β‐pyrrolic positions have been prepared and characterized by NMR, UV/Vis near‐infrared (NIR), high‐resolution mass spectrometry, and fluorescence spectroscopy, as well as X‐ray crystallography. The redox properties of new BOPHYs were probed by electrochemical (cyclic and differential pulse voltammetry) and spectroelectrochemical methods. In an attempt to prepare BOPHY derivatives with a cyano group at the bridging position using a similar approach for BODIPY cyanation, adducts from the nucleophilic attack of the cyanide anion on the bridging position in BOPHY have been isolated and characterized by spectroscopic methods. Oxidation of such adducts, however, resulted in formation of either the starting BOPHYs, or partial extrusion of the BF 2 fragment from the BOPHY core, which was confirmed by spectroscopy and X‐ray crystallography. DFT and TDDFT calculations on all target materials correlate well with the experimental data, and suggest the dramatic reduction of the nitrogen atom basicity at the hydrazine bridge of the BOPHY upon introduction of the cyano group at the bridging‐carbon atom.

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)0.001
metaresearch head score (Gemma)0.000
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 score0.068
Threshold uncertainty score0.863

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0010.001
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

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 head0.226
Teacher spread0.208 · 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.

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

Citations44
Published2017
Admission routes2
Has abstractyes

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