Luminescent <i>N</i>-aryl-heteroacene derivatives
Bibliographic record
Abstract
The incorporation of heteroatoms into polycyclic aromatic hydrocarbons can alter their optical and electronic properties. Here, we report the synthesis and characterization of a series of N,N′-diaryl diazadioxatetrahydropentacenes (4a–e) as well as related N-phenyl azatrioxatetrahydropentacene and triazatetrahydrotetracene derivatives (5, 6) to investigate their photophysical properties and solid-state organization. These compounds were prepared from readily available compounds via a concise approach involving copper-catalyzed aryl amination, followed by nucleophilic aromatic substitution. The compounds display bright luminescence in solution and in the solid state and strong solvatochromism. Single-crystal X-ray diffraction of N,N′-aryl diazadioxatetrahydropentacenes (4b–d) revealed that all the compounds possessed nearly planar polycyclic aromatic systems with the pendant aryl groups nearly orthogonal to the pentacyclic core. Nonetheless, different substituents on the pendant aryl groups resulted in differences in photophysical properties because of differences in molecular geometries and solid-state packing. Interestingly, the N,N′-aryl diazadioxatetrahydropentacene bearing 2,6-dimethylphenyl groups attached to the nitrogen atoms (4d) gave two different polymorphs from the same solvent system, constituting a relatively rare example of concomitant polymorphism for such a rigid structure.
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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".