Synthesis and Characterization of β-Trifluoromethyl-<i>m</i><i>eso</i>-tetraphenylporphyrins
Bibliographic record
Abstract
Beta-trifluoromethyl-meso-tetraphenylporphyrins were synthesized to investigate the electronic and steric effects of the trifluoromethyl groups on the macrocycle. Preparation of these novel porphyrins was carried out by copper-assisted trifluoromethylation of beta-tetrabromo-meso-tetraphenylporphyrin metal complexes and in situ generated CF3Cu. For comparison, the beta-methyl analogues were also prepared. Analysis of beta-trifluoromethylporphyrins by UV-vis, NMR, and cyclic voltammetry (CV) showed that the electron-withdrawing effects of the trifluoromethyl groups on the antipodal pyrroles required the macrocycle to take a fixed 18pi-electron pathway. UV-vis, CV, and molecular modeling studies suggest that the novel porphyrins are distorted following introduction of trifluoromethyl groups onto the pyrrolic beta-position of meso-tetraphenylporphyrin. The pK(a) difference of beta-tetrakis(trifluoromethyl)-meso-tetraphenylporphyrin from that of DBU in CH2Cl2, obtained by spectrophotometric titration, affirms that it is one of the most electron-deficient porphyrins so far prepared.
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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".