The First Electronically Stabilized Phenalenyl Radical: Effect of Substituents on Solution Chemistry and Solid-State Structure
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Bibliographic record
Abstract
We report an investigation into the effect of oxygen and sulfur substitution on the dimerization of phenalenyl-based neutral radicals; these substituents are expected to electronically stabilize the free radical while sterically interfering with dimerization. The 1,3,4,9-tetramethoxyphenalenyl ( 7a ) and 1-ethoxy-3,4,9-trimethoxyphenalenyl ( 7b ) radicals are prepared by chemical reduction of the cation salts, but the crystals that are isolated from these solutions are shown to be composed of alkoxy-substituted peropyrenes by X-ray crystallography. Crystallization of 1,9-dithiophenalenyl ( 8 ) gives rise to a π-dimer, and this is the first example of a radical based on a single phenalenyl unit that has been stabilized against σ-dimerization in the solid state by electronic effects rather than by the presence of sterically bulky substituents.
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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 | 0.002 | 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 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
Machine scores (provisional)
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Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
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