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
High Resolution Image Download MS PowerPoint Slide The first set of phenoxy BsubNc compounds, PhO-Cl n BsubNc and F 5 -Cl n BsubNc, was synthesized through an axial displacement reaction of Cl-Cl n BsubNc with phenol and pentafluorophenol (respectively). Like their precursor, the products were found to be an alloyed mixture of phenoxylated Cl n BsubNcs 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-Cl n BsubNc. Although the phenoxylation of Cl-Cl n BsubNc 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 ( V OC ) was observed, ultimately exceeding 1.0 V when phenoxylated Cl n BsubNcs 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 Cl n BsubNcs, when paired with poly-3-hexylthiophene, also showed high V OC 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 Cl n BsubNcs with nonchlorine axial substituents in OPVs and demonstrates that phenoxylation has a significant impact on device metrics while enhancing solubility to enable incorporation of Cl n BsubNcs into BHJ OPVs.
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How this classification was reachedexpand
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 | 0.001 | 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 | 0.001 | 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) | 0.000 | 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 teacher head, 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".