Synthesis of a Perylene Diimide Dimer with Pyrrolic N–H Bonds and N‐Functionalized Derivatives for Organic Field‐Effect Transistors and Organic Solar Cells
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Bibliographic record
Abstract
This study reports on the new and optimized synthesis of an N‐annulated perylene diimide dimer with functional N–H moieties. The presence of two N–H moieties renders the dimer relatively insoluble in most organic solvents. The dimer is easily functionalized with electron donating hexyl chains or electron withdrawing tert ‐butyloxycarbonyl (tBOC) groups to yield highly soluble materials. The tBOC groups can be thermally cleaved in the thin film to give the parent dimer. The N–H bonds are acidic and interact with volatile organic bases. Deprotonation results in a color change from red to blue. All compounds have utility as electron transport materials in organic field‐effect transistors and green solvent, air processed organic solar cells. Electron mobilities were on the order of about 2–7 × 10 –6 cm 2 /V s. Solar cell power conversion efficiency reached 2 % for those using the tBOC functionalized dimer, 3 % for those using the H‐atom functionalized dimer, and 6 % for those using the hexyl chain functionalized dimer. The performance of the latter is quite impressive considering the simple materials synthesis and greener solar cell processing.
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Full frame distilled prediction
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 | 0.000 | 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 it