2,3,4,5-Tetrafunctionalized Siloles: Syntheses, Structures, Luminescence, and Electroluminescence
Bibliographic record
Abstract
Six new diethynylsilane compounds with the general formula Si(C⋮C−R) 2 R‘ 2 (R = p - N- indolylphenyl, R‘ = Me, 1; R‘ = Ph, 2; R = p - N- 7-azaindolylphenyl, R‘ = Me, 3; R‘ = Ph, 4; R = p- 2,2‘-dipyridylaminophenyl, R‘ = Me, 5; R‘ = Ph, 6 ) have been synthesized and fully characterized. Compounds 1, 2, and 4 have been found to undergo intramolecular cyclization in the presence of Li-naphthyl to form the corresponding 2,5-dilithiosiloles, which after methylation by CH 3 I or undergoing Pd-catalyzed cross-coupling reactions with the appropriate arylbromide produced six new silole compounds: 1,1-diphenyl-2,5-dimethyl-3,4-bis(4- N -7-azaindoylphenyl)silole ( 7 ), 1,1-diphenyl-2,3,4,5-tetrakis(4- N -indoylphenyl)silole ( 8 ), 1,1-dimethyl-2,5-bis(4- N -7-azaindoylphenyl)-3,4-bis(4- N -indoylphenyl)silole ( 9 ), 1,1-dimethyl-2,5-bis( p -2,2‘-dipyridylaminophenyl)-3,4-(4- N -indoylphenyl)silole ( 10 ), 1,1-dimethyl-2,5-bis(4-( N -1-naphthylphenylamino)phenyl)-3,4-bis(4- N -indoylphenyl)silole ( 11 ), and 1,1-dimethyl-2,5-bis(4‘-( N -1-naphthylphenylamino)biphenyl)-3,4-bis(4- N -indoylphenyl)silole ( 12 ). Compounds 8 − 12 are a new class of silole molecules that are functionalized at the 2-, 3-, 4-, and 5-positions by indolylphenyl, 7-azaindolylphenyl, 2,2‘-dipyridylaminophenyl, ( N- 1-naphthyl)( N- phenyl)aminophenyl, or ( N- 1-naphthyl)( N- phenyl)aminobiphenyl. The structures of compounds 3, 5, and 8 were determined by single-crystal X-ray diffraction analysis. Siloles 8 − 12 emit a green color in solution and the solid state, while in contrast silole 7 emits a blue color with the emission maximum at 445 nm. The effects of substituent groups at different positions of the silole ring on structures and luminescent properties have been examined. A single-layer EL device with compound 11 being sandwiched between the ITO anode and the LiF/Al cathode layers has been fabricated successfully.
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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 | 0.001 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.002 | 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".