Peripherally Fluorinated Silicon Phthalocyanines: How Many Fluorine Groups Are Necessary for Air-Stable Electron Transport in Organic Thin-Film Transistors?
Bibliographic record
Abstract
Silicon phthalocyanines (R 2 –SiPcs) are an emerging class of high-performance n-type semiconductors used in organic electronics, which historically have suffered from operational instability in air. We report the synthesis of R 2 –SiPcs with varying degrees of peripheral fluorination, R 2 –F x SiPcs ( x = 0, 4, or 16), and different axial phenoxy groups leading to 12 derivatives with 0 to 26 fluorine atoms in the molecular structure and going from non-operational devices in ambient conditions to fully air-stable operation in organic thin-film transistors (OTFTs). Ultraviolet photoelectron spectroscopy revealed that the peripheral fluorination of R 2 –F x SiPcs caused a decrease of up to 0.9 eV in the energy level of the lowest unoccupied molecular orbital (LUMO). This reduction in the LUMO energy level coincides with a decrease in the threshold voltage ( V T ) of the resulting OTFT. All compounds containing 16 peripheral fluorine atoms and one of four compounds containing four peripheral fluorine atoms in OTFTs yielded air-stable electron transport in ambient conditions at a humidity of 40%. Power spectral density functions (PSDF) from atomic force microscopy imaging also demonstrated that for similar morphologies across a series of compounds with the same axial group, a larger domain size and a smaller density of grain boundaries in the film led to a higher overall electron mobility (μ e ).
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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 | 0.001 |
| 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".