Synthesis of <i>bis</i>indolyl diphenylene from its ketone derivatives by infrared irradiation supported on a natural clay
Bibliographic record
Abstract
We examined the near-infrared (NIR) light-induced assembly efficiency to obtain light-sensitive 3,3′-(9H-fluorene-9,9-diyl) bis(1H-indole) derivatives using natural clay as metal-free Brønsted–Löwry catalyst (bentonitic Tonsil–Actisil FF (TAFF) clay) and an adduct of aluminum (III) chloride with 9-fluorenone. Their mixtures in solventless and aprotic solvent conditions were also explored. Among all the modified reactions tested, the combined effects of TAFF natural clay with NIR light, specifically in the λ1.1 µm spectral region, result especially efficient to achieve the formation of C–Cπ bonds between π-excessive azaheteroaromatic reagents and functionalized polycyclic aromatic hydrocarbon to give the title compound in good yields within reasonable reaction times. The reaction coordinate was obtained using quantum chemical calculations. All the reactants, products, intermediates, and transition states were obtained for four systems. Natural orbital analysis allowed us to rationalize the transformations. Overall, this approach represents a greener and equally efficient alternative for conducting C–Cπ bond construction reactions in organic chemistry, and it is especially useful for protecting photosensitive compounds from abrupt decomposition.
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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".