Synthesis and Photophysics of Thioindigo Diimines and Related Compounds
Bibliographic record
Abstract
We report the synthesis and comprehensive characterization of diamine and diimine derivatives of the fluorescent compound thioindigo. Diamines 1 were obtained by metal-mediated amine condensation reaction with thioindigo. Oxidation of the products of the coupling reaction provided the diimines 2. X-ray crystal structures, cyclic voltammetry, and spectral and photophysical data of the compounds are presented. X-ray crystal structures demonstrate a planar structure for the diimine derivatives and a twisted conformation for the diamines. The diamine compounds 1 absorb in the UV (λmax 324-328 nm), significantly blue-shifted from the absorption spectrum of thioindigo. Diamines 1 exhibit moderate fluorescence (ΦF = 0.25, 0.045). A transient triplet state is observed in laser flash photolysis (LFP) experiments of 1, with lifetimes 1 order of magnitude longer than those of thioindigo. The diimine compounds 2 absorb at longer wavelengths (λmax 495-510 nm) than the diamines but are still slightly blue-shifted from thioindigo, with molar extinction coefficients 17-70% higher compared to thioindigo. The diimine compounds are not emissive, and LFP studies indicate transient species with microsecond lifetimes. Quenching experiments and transient absorption spectra are consistent with trans-cis isomerization.
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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 | 0.000 | 0.001 |
| 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 teacher head, 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".