Non-symmetric benzo[b]-fused BODIPYs as a versatile fluorophore platform reaching the NIR: a systematic study of the underlying structure–property relationship
Bibliographic record
Abstract
Ten newly synthesized non-symmetric benzo[b]-fused BODIPYs are compared with an extended series of nine related families (23 compounds) to gain insights into their structure-property relationship. The insertion of a fused indole moiety into the dipyrromethene core and various substituents on the proximal aryl including fused aromatic groups, lead to pronounced changes in the properties of compounds . By taking advantage of this versatile synthetic platform that allows facile substituent modifications and extension of the π-conjugated system, significant bathochromic shifts in the absorption (λmax = 511-597 nm) and emission (601-757 nm) bands are achieved. Although the oxidation potentials of the compounds vary considerably throughout the series (+1.28-+1.65 V) due to the significant contribution of the aryl function to the HOMO, the reduction remains much more consistent (-0.61 to -0.79 V) as the LUMO resides primarily on the dipyrromethene core with little aryl contribution as calculated by DFT. For example, installation of a dimethylamine substituent in the para position of the aryl group leads to drastic modification of the optoelectronic properties of the absorption (597 nm) and emission (757 nm) maxima. The full electrochemical, photophysical and computational analyses of the compounds along with the structural characterization of compounds , , , and are used to rationalize the potential of this powerful platform.
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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) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.001 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 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".