Formation of 8-RS-BODIPYs via direct substitution of 8-MeS-BODIPY by RSH (R = Et, Pr, Bu, <sup>t</sup>Bu, <i>n</i>-C<sub>12</sub>H<sub>25</sub>, C<sub>6</sub>H<sub>5</sub>, <i>p</i>-MeC<sub>6</sub>H<sub>4</sub>, <i>p</i>-MeOC<sub>6</sub>H<sub>4</sub>, and 2,6-Me<sub>2</sub>C<sub>6</sub>H<sub>3</sub>)
Bibliographic record
Abstract
Reactions between 8-RS-BODIPY (R = Me, 1) and alkyl and aryl thiols were readily accomplished in dichloromethane to provide a synthetic pathway to a range of new 8-organothio-BODIPYs in good yield. The new alkyl 8-RS-BODIPYs (R = Et, 2; Pr, 3; Bu, 4; tBu, 5; n-dodecyl, 6) exhibit absorption and emission properties essentially unchanged from those of 1 whereas the arylthio analogs (R = Ph, 7; 2,6-Me2C6H3, 8; p-MeC6H4, 9; p-MeOC6H4, 10) exhibit no fluorescence with the exception of 7, and then only in hexane. In common with other related 8-substituted BODIPYs, the new 8-alkylthio-BODIPY dyes show decreasing fluorescence intensity as solvent polarity increases. Compounds 2, 3, 7, and 8 were characterized via single-crystal X-ray analysis; the alkyl derivatives 2 and 3 exhibited planar BODIPY cores with co-planar organothio- substituents whereas the aryl derivatives exhibited both BODIPY core deformation and significant twisting about the S–C (8) bond removing co-planarity between the aryl group and the distorted BODIPY core. These deformations coincide with the significantly reduced emission properties.
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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 | 0.001 |
| 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; 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".