Ring fusion isomers of dithienoborepins: perturbations of electronic structure, aromaticity, and reactivity in boron-containing polycyclic heteroaromatics
Bibliographic record
Abstract
Through a combination of rational design and synthetic serendipity, two new structural isomers of the dithienoborepin (DTB) architecture have been realized. Unlike previous members of this family, these boron-containing polycyclic aromatics are unsymmetrical with respect to the fusion orientation of the central borepin and flanking thiophene rings. Characterization of the unsymmetrical dithienoborepins through spectroscopic, crystallographic, electrochemical, and computational methods reveal that the electronics, aromaticity, and chemical reactivity can differ subtly (as for DTB 3) or in dramatic fashion (DTB 4) throughout the series, as dictated by the nature of the unique π-conjugation in each structure. Synthetic elaboration of the three most closely related DTB isomers (1, 2, and 3) into π-extended derivatives by Pd-catalyzed cross-couplings revealed an enhancement in their inherent electronic property differences, demonstrating the feasibility of such an approach for molecular property tuning.
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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".