Impact of the Linker on the Electronic and Luminescent Properties of Diboryl Compounds: Molecules with Two BMes<sub>2</sub> Groups and the Peculiar Behavior of 1,6-(BMes<sub>2</sub>)<sub>2</sub>pyrene
Bibliographic record
Abstract
To investigate the impact of the linker on the electronic and photophysical properties of diboryl compounds, three new diboryl compounds that contain two BMes 2 groups (Mes = mesityl) have been synthesized, including a planar 1,6-(BMes 2 ) 2 pyrene ( 1 ), a V-shaped bis( p -BMes 2 phenyl)diphenylsilane ( 4 ), and a U-shaped 1,8-bis( p -BMes 2 phenyl)naphthalene ( 5 ). For comparison, two previously known compounds, p- (BMes 2 ) 2 benzene ( 3 ) and 1,8-bis( p -BMes 2 -biphenyl)naphthalene ( 6 ), were also investigated. The aromatic linkers in these molecules have been found to have a dramatic impact on the electron-accepting ability and Lewis acidity of the diboryl compounds through their distinct steric and electronic properties. Compound 1 has the most positive reduction potential ( E 1/2 red1 = −1.81 V, relative to FeCp 2 0/+ ), while 5 has the most negative reduction potential ( E 1/2 red1 = −2.34 V). All compounds are blue emitters with considerable variation of emission energy and efficiencies (e.g., λ em = 446, 402, 395 nm, Φ = ∼1.0, 0.17, ∼1.0 for 1, 4, and 5, respectively), and each displays a distinct and selective response toward fluoride ions. Upon addition of fluoride ions, compound 1 displays an unusual red shift and an on−off response in both absorption and fluorescent spectra. By comparing the behavior of 1 to that of the monoboryl compound 1-BMes 2 pyrene ( 2 ) and 3, and with TD-DFT computations on 1 and its fluoride adducts 1F and 1F 2, it has been found that the peculiar response of 1 toward fluoride ions is caused by the dominance of pyrene π orbitals at the HOMO level of 1F and the relatively low-energy charge transfer from the pyrene ring to the three-coordinate boron center in 1F . The crystal structures of 2, 4, 1F 2, and 5F 2 were determined by X-ray diffraction analyses. The potential use of compound 1 as either a blue emitter or a bifunctional emitter in OLEDs has been demonstrated by the successful fabrication of double- and triple-layer electroluminescent devices.
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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) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.003 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| 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".