Facile Synthesis of Isomeric Hexacyanopyidine Triphenylene Derivatives
Bibliographic record
Abstract
Abstract Four isomeric hexacyanopyridine triphenylene derivatives were synthesized and characterized. Prepared in three synthetic steps, they were isolated in very good yields (higher than 85%), without flash chromatography. Their identities and purities were proved by high‐resolution mass spectrometry (HRMS), infrared (IR), and nuclear magnetic resonance (NMR) spectroscopy, and CHN elemental analysis. All compounds show high thermal stability (up to ∼400 °C), as determined by thermogravimetric analyses (TGA). Their absorption and emission properties were also investigated. In line with the presence of aromatic moieties in their structures, they exhibit UV (250–325 nm) π to π* electronic transitions, with slight variations among different isomers. They all show emission profiles similar to those of other triphenylene derivatives (fluorescence band at 350–400 nm), while, interestingly, one of the isomers additionally presents a lower energy (473 nm) broad band, assigned to aggregation phenomena. Single‐crystal X‐ray diffraction solid‐state structures were obtained for two of the compounds, showing that, in the solid state, the columnar organization of triphenylene cores is impeded by the presence of cyanopyridine moieties. Hydrogen bonding analysis illustrates the presence of strong and weak hydrogen bonding in both structures. Hirshfeld surface analysis was additionally performed to better understand the crystal packing interactions.
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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) | 0.002 | 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".