Impurities in Arylboronic Esters Induce Persistent Afterglow
Bibliographic record
Abstract
Several recent reports suggest that arylboronic esters can exhibit room temperature phosphorescence (RTP), an optical property that is desirable for applications in security printing, oxygen sensing, and bioimaging. These findings challenged the fundamental notion that heavy elements or changes in orbital symmetry were required for intersystem crossing to occur in organic compounds. As we had not observed long afterglow in the many arylboronic esters we had synthesized over many years, we suspected that the RTP observed in these systems had a simpler explanation: the materials reported were impure. Herein, we synthesized 12 arylboronic esters that were previously reported to show RTP, and carefully purified them by column chromatography, recrystallization, and sublimation. We re-examined their photophysical properties alongside single-crystal X-ray diffraction analysis and detailed theoretical studies. While 4 of the 12 compounds showed long afterglows as crude products, none of them showed persistent RTP after careful purification. We also successfully isolated the impurity 4-amino-3,5-bis(pinacolatoboryl)benzonitrile ( 2 ), identifying it as the impurity responsible for inducing delayed fluorescence in 3,5-bis(pinacolatoboryl)benzonitrile ( 1 ). Doping 1 with 1.0 mol % 2 led to a persistent afterglow with a lifetime of 67 ms, which is mediated by a dimer charge transfer state. Our findings call for a re-examination of previous studies reporting RTP from arylboronic esters, highlight the importance of careful purification in photophysical research, and provide a practical strategy for designing organic materials with a long afterglow.
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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) | 0.001 | 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".