Boron Subphthalocyanines and the Exploration of Other p-Block Metal Phthalocyanines for Use in Organic Electronics
Bibliographic record
Abstract
For some time our group has been focused on the design and synthesis of derivatives of boron subphthalocyanine (BsubPc) for application in organic electronics. In most cases, organic electronic devices utilize the prototypical BsubPc, chloro boron subphthalocyanine (Cl-BsubPc). We have shown that by using facile chemical transformations we can tailor the nature of the BsubPc to a dye, sublimate, engineered crystal or polymer. Early on in our research program we showed that peripheral functionalization of the BsubPc moiety had detrimental effects on the electrochemical behavior/stability. We therefore focused on chemical derivatization of the boron metal centre while maintaining the hydrogen periphery. The chemical transformations we have found most successful rely on the oxo-philicity of the boron metal centre. In this presentation I will outline examples of each type of BsubPc, the chemistry we used to achieve each derivative, in addition to presenting their application in organic electronic devices including organic light emitting diodes (OLEDs) and organic photovoltaics (OPVs). I will also highlight our group’s recent interest in expanding our methodology to other p-block metal phthalocyanines (M-Pcs) including Pcs of aluminum, silicon, germanium and phosphorous. In each case the metal was chosen due to its abundance and its ability to participate in our previously established oxo-philic based chemistry. Preliminary organic electronic device data will also be presented. Coauthors will be cited as appropriate throughout the presentation. Leading References: (1) “Pentafluorophenoxy Boron Subphthalocyanine (F5BsubPc) as a Multifunctional Material for Organic Photovoltaics.” Morse, G.E.; et al. ACS Appl. Mat. Inter., 2014, 6 (3), 1515–1524. (2) “Utilizing the π-Acidity of Boron Subphthalocyanine to Achieve Novel Solid-State Arrangements.” Paton, A.S.; et al. Crystal Growth & Des., 2013, 13 (12), 5368–5374. (3) “Halogen bonds can direct the solid state arrangement of phenoxy-boron subphthalocyanines.” Virdo, J.D.; et al.CrystEngComm, 2013, 15, 3187-3199. Figure 1
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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 | 0.001 |
| Insufficient payload (model declined to judge) | 0.002 | 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".