New benzo-9-crown-3 functionalized aryl imides for the capture and release of lithium ions from solution
Bibliographic record
Abstract
With an increased demand for lithium ion (Li-ion) battery technologies, and the small number of lithium mines around the globe, there has been a heightened desire to develop new materials capable of extracting lithium from aqueous sources such as the ocean. To do so in an economically viable way, the materials must be highly selective toward the extraction of Li-ions so as not to necessitate the further purification from competing metal ions such as magnesium, sodium, or calcium. To address this, herein we report on three new conjugated imide compounds functionalized with the crown ether benzo-9-crown-3. The three new compounds Phth-CE, F-Phth-CE, and NMI-CE were synthesized via atom-economical condensation reactions between an amino functionalized benzo-9-crown-3 with commodity aryl imide building blocks. These three new compounds serve to develop an understanding of Li-ion capture via the benzo-9-crown-3 moieties scaffolded onto stable aromatic ring systems. The nodal plane between the aryl imide and the phenyl ring of benzo-9-crown-3 isolates the crown ether allowing for unhindered Li-ion capture and release. Subtle derivatization of the aryl imide showcases structural versatility to include a fluoride amenable to nucleophilic aromatic substitution and/or to act as a diagnostic handle and naphthalene unit extending optical absorption to longer wavelengths. Each new compound exhibits the formation of Li-ion sandwich complexes as determined by 7 Li NMR spectroscopy, and near identical Li-ion extraction efficiencies, distribution coefficients, and selectivity under acidic conditions in neat and mixed-metal ion solutions as determined by triple quadrupole inductively coupled plasma mass spectrometry analysis.
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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 | 0.001 |
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".