Redox-active, near-infrared dyes based on ‘Nindigo’ (indigo-N,N′-diarylimine) boron chelate complexes
Bibliographic record
Abstract
Reactions of indigo-N,N′-diarylimine (‘Nindigo’) derivatives with BF3·Et2O give mono- or bis-BF2 chelate complexes 2 or 3 respectively. The product distribution between 2 and 3 is sensitive to the auxiliary base and solvent. Although the bis-BF2 complexes 3 are isolable, they gradually decompose in solution to the corresponding mono-BF2 species 2; this process is accelerated by water. The instability of 3 is believed to be due to ring stain effects based on structural analyses of 2. Electrochemical studies of 2 reveal one quasi-reversible oxidation process and two irreversible reductions, whereas derivatives of 3 possess a reversible oxidation and two sequential reversible reductions. The electronic spectra of 2 and 3 contain intense (ε ∼ 3 × 104 M−1 cm−1) long-wavelength absorptions near 650 nm and 750 nm respectively. Both series of compounds are weakly emissive in the near-infrared. Time-dependent DFT calculations reveal the electronic transitions to be π–π* in nature.
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How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot 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.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.001 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.001 | 0.002 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.002 | 0.001 |
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.
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; both teacher heads agree on what is shown here.
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".