Phenoxy-(Chloro)<sub><i>n</i></sub>-Boron Subnaphthalocyanines: Alloyed Mixture, Electron-Accepting Functionality, and Enhanced Solubility for Bulk Heterojunction Organic Photovoltaics
Bibliographic record
Abstract
Abstract The first set of phenoxy BsubNc compounds, PhO-ClnBsubNc and F5-ClnBsubNc, was synthesized through an axial displacement reaction of Cl-ClnBsubNc with phenol and pentafluorophenol (respectively). Like their precursor, the products were found to be an alloyed mixture of phenoxylated ClnBsubNcs with random positioning in the solid state yet consistent frequency of bay position chlorination. The average bay position chlorine occupancy was determined to be 0.99 through single crystal diffraction of PhO-ClnBsubNc. Although the phenoxylation of Cl-ClnBsubNc did not influence the chromophore photophysical properties, the electrochemical behavior was found to be more stable. Phenoxylation yielded differences in organic photovoltaic (OPV) device metrics. Specifically, a significant increase in open circuit voltage (VOC) was observed, ultimately exceeding 1.0 V when phenoxylated ClnBsubNcs were paired with alpha-sexithiophene (α-6T) in planar heterojunction OPVs. Phenoxylation enabled the first example of BsubNcs incorporated into polymer-based bulk heterojunction (BHJ) OPVs through enhanced solubility. Phenoxylated ClnBsubNcs, when paired with poly-3-hexylthiophene, also showed high VOC in BHJ OPVs with broad spectral absorption up to 760 nm. In the BHJ case, simple phenoxy was shown to be a better axial substituent compared to pentafluorophenoxy. This study represents the first example of using ClnBsubNcs with nonchlorine axial substituents in OPVs and demonstrates that phenoxylation has a significant impact on device metrics while enhancing solubility to enable incorporation of ClnBsubNcs into BHJ OPVs.
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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".