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.
Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.
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 | 0.001 |
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".