BODIPY derivatives with diverse meso-aryl groups – the influence of chemical structure alterations on their electrochemical and optical properties
Bibliographic record
Abstract
ABSTRACT Electrochemical and optical studies in an organic environment were performed on eight boron-dipyrromethene derivatives with various aromatic meso substituents. The influence of an extended π-electron system or the introduction of alkyl substituents into the pyrrolyl moieties was assessed, revealing significant changes in redox processes. Two redox pairs were observed in compounds with single aromatic meso residues, whereas four or five were found in the case of extended π-electron systems of derivatives 2 and 4-6 . Applying a negative potential resulted in the formation of anionic species only in one studied BODIPY 8 with methoxy-phenyl groups, as observed by UV-Vis. The optical properties of the BODIPY derivatives were also investigated, revealing that structural modifications induced the redshift of S 0 →S 1 transition bands. Experimental UV-Vis spectra and electrochemical band gaps were compared with the theoretical results derived from time-dependent density functional theory (TD-DFT) calculations using IEFPCM and SMD models. The computed data were in good agreement with the experimental ones, indicating the highest band gap values in compounds 1-3 , along with the lowest for derivative 4 with pyrene moiety. Moreover, the computational studies revealed B3LYP and PW6B95D3 as the most accurate functionals for band gap predictions. These findings provide valuable insights into the structure-property relationships of BODIPY derivatives, offering a predictive framework for tuning their electronic and optical properties through targeted structural modifications. By elucidating how meso-substituents influence the electrochemical and optical properties of BODIPY derivatives, this study advances the rational design of functional materials for optoelectronic and sensing applications.
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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".