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
Bibliographic record
Abstract
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 BF2 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.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot 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.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.001 | 0.000 |
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.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.
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".