Tin can milling: low-tech mechanochemical synthesis of plant-based prepolymers incorporating perfluoropyridine
Bibliographic record
Abstract
Perfluoropyridine (PFP) is a fluorinated small molecule heterocycle which can undergo a variety of substitutions in the 2-, 4-, and 6-position to afford rationally designed prepolymers. PFP is known to undergo mechanochemical substitutions, however ball mills have a large start-up cost and are bulky, creating a barrier of entry for researchers. We sought to provide a low tech, affordable, reproducible, and space-saving methodology towards general mechanochemistry while retaining the ability to work on gram scale. Herein we report the successful application of tin can milling (TCM) towards the gram scale synthesis of 4-tetrafluoropyridines (24 examples, up to ≥99% conversion) using a tomato paste can, aluminum beads, a rubber stopper, and agitation with a Burrell Wrist Action™ shaker unit. This approach eliminates problems of scalability with a mortar and pestle and provides a clean method to do benchtop-scale mechanochemistry without additional equipment. We further apply this technique towards making natural product-based prepolymers for polymerization by inverse vulcanization as a proof-of-concept for the use of TCM in monomer synthesis.
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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".