Optimizing the preparation of bromo phthalonitriles and piloting them to peripherally brominated boron subphthalocyanines
Bibliographic record
Abstract
Boron subphthalocyanines (BsubPcs) are versatile molecules with advantageous properties for applications. The BsubPcs are synthesized by the cyclotrimerization of a phthalonitrile and are composed of three isoindole subunits bound by three aza-/imine-bridging nitrogens. There are a variety of BsubPc derivatives shown within the literature due to the differentiation of a phthalonitrile precursor. The differentiation of a phthalonitrile enables the peripheral functional groups. The BsubPcs can be derivatized in two steps: First step is the cyclotrimerization of a phthalonitrile in the presence of a strong Lewis Acid, typically a boron trihalide (BX3) and enables a remaining axial substituent that is a B-X[Formula: see text] bond; second step is optional, the B-X[Formula: see text] bond can react with a nucleophile and results in B-X[Formula: see text]. If the starting phthalonitrile is asymmetric, it will result in a combination of isomers. For this study, our approach is to have bromine substituents and to study their physical properties to see if applicable to organic electronic applications; chlorine and fluorine have been in past studies as halogens are unique and variations may present useful tools as they are known for electronegativities. The general phthalonitrile with no substitutions is produced in industry from [Formula: see text]-xylene. There are a variety of ways to synthesize other phthalonitriles with halogens. However, phthalonitriles can also be made by a method that has the most versatility with its substituents and can start with phthalic acid and go to phthalic anhydride to phthalimide to phthalamide and final to phthalonitrile; it is also possible to synthesize a phthalimide directly from phthalic acid, and this is part of this study as we were focusing on bromination, we also wanted to optimize the synthetic pathways to brominated phthalonitriles, and we took an engineering perspective and for this study, we wish to show you.
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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) | 0.001 | 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) | 0.000 | 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".