Investigation of Triphenylamine–Thiophene–Azomethine Derivatives: Toward Understanding Their Electrochromic Behavior
Bibliographic record
Abstract
A series of thiophenoazomethines connected to a central triphenylamine were prepared. The effect of the type of aminothiophene used to prepare the conjugated azomethines and the number of azomethine bonds, ranging from one to three, flanking the triphenylamine on the spectral, electrochemical, and spectroelectrochemical properties were investigated. Both the absorption and fluorescence of the azomethines ( 6 – 8 ) derived from 2,5-diaminothiophene ( 1 ) were found to be contingent on the number of the azomethines. The spectral properties were red-shifted with increasing the number of azomethine bonds. In contrast, the azomethines ( 9 – 11 ) derived from 2-aminothiophene ( 2 ) were not perturbed by the number of azomethines. However, their spectral properties were red-shifted relative to their triphenylamine counterparts derived from 1 . The oxidation potentials of the azomethines were also contingent on structure. They were shifted to more positive potentials with increasing number of azomethines. The oxidation potentials of 6 – 8 were less positive than 9 – 11, owing to the electron-donating effect of the terminal amine. Reversible oxidation was observed with the triphenylamine having methyl groups in the 4′-positions. All the compounds examined underwent color changes upon both electrochemical and chemical oxidation. The oxidized state was shifted upward of 165 nm for the series 6 – 8 relative to the neutral state, whereas it was shifted at most by 85 nm for 9 – 11 . The most pronounced color changes between the neutral and oxidized states occurred with the triphenylamine–thiophene–triphenylamine bisazomethine derivative ( 12 ).
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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 | 0.000 | 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) | 0.000 | 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".