Superacid-Catalyzed Polycondensation of Acenaphthenequinone with Aromatic Hydrocarbons
Bibliographic record
Abstract
A novel series of linear, high molecular weight polymers were synthesized by one-pot, superacid-catalyzed reaction of acenaphthenequinone ( 1 ) with aromatic hydrocarbons. The reactions were performed at room temperature in the Brønsted superacid CF 3 SO 3 H (trifluoromethanesulfonic acid, TFSA) and in a mixture of TFSA with methanesulfonic acid (MSA) and trifluoroacetic acid (TFA), which was used as both solvent and a medium for generation of electrophilic species from acenaphthenequinone. The polymer-forming reaction was found to be dependent greatly on the acidity of the reaction medium, as judged from the viscosity of the polymers obtained. Polycondensations of acenaphthenequinone with 4,4‘-diphenoxybenzophenone ( f ), 1,3-bis(4-phenoxybenzoyl)benzene ( g ), 1,4-bis(4-phenoxybenzoyl)benzene ( h ), 1,10-bis(4-phenoxyphenyl)decane-1,10-dione ( i ), 2,6-diphenoxybenzonitrile ( j ), 2,6-diphenoxybenzoic acid ( k ), and 2-(4-biphenylyl)-6-phenylbenzoxazole ( l ) proceeded in a reaction medium of wide range of acidity, including pure TFSA (Hammett acidity function H 0 of pure TFSA is −14.1), whereas condensation of 1 with biphenyl, terphenyl, diphenyl ether, and 1,4-diphenoxybenzene needed a reaction medium of acidity H 0 less than −11.5. A possible reaction mechanism is suggested. The polymers obtained were found to be soluble in the common organic solvents, and flexible transparent films could be cast from the solutions. 1 H and 13 C NMR analyses of the polymers synthesized revealed their linear, highly regular structure. The polymers also possess high thermostability. Char yields for polymers 3a, 3c, 3d, and 3l in nitrogen were close to 80% at 1000 °C.
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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) | 0.001 | 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 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".