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Record W1995501560 · doi:10.1021/ma0203694

Synthesis and Characterization of Water-Soluble Cationic and Anionic Polyferrocenylsilane Polyelectrolytes

2002· article· en· W1995501560 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueMacromolecules · 2002
Typearticle
Languageen
FieldMaterials Science
TopicPolymer Surface Interaction Studies
Canadian institutionsUniversity of Toronto
Fundersnot available
KeywordsCationic polymerizationChemistryPolyelectrolytePolymer chemistryPolymerizationReagentBromideRing-opening polymerizationPolymerSubstituentLithium (medication)Medicinal chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

Convenient routes to a range of water-soluble polyferrocenylsilane polyelectrolytes are reported. Direct reaction of the protected aminopropynyl reagent LiC⋮CCH 2 N(SiMe 2 CH 2 ) 2 ( 8 ) with the substitutionally labile ring-opened polymer [fcSiMeCl] n ( 3 ) (fc = Fe(η−C 5 H 4 ) 2 ), which is generated via Pt-catalyzed ring-opening polymerization of the silicon-bridged [1]ferrocenophane fcSiMeCl ( 6 ), afforded the polymer [fcSiMe{C⋮CCH 2 N(SiMe 2 CH 2 ) 2 }] n ( 10 ). Polymer 10 was also obtained via ring-opening polymerization of the [1]ferrocenophane fcSiMe{C⋮CCH 2 N(SiMe 2 CH 2 ) 2 } ( 9 ) prepared from the reaction of the lithium salt 8 and the substitutionally labile [1]ferrocenophane 6, which is readily accessible via the reaction of fcLi 2 ·TMEDA with MeSiCl 3 . Deprotection of 10 was readily achieved using THF/MeOH to yield [fcSiMe(C⋮CCH 2 NH 2 )] n ( 11 ), which was conveniently reduced with hydrazine to the analogous aminopropyl polymer [fcSiMe(CH 2 CH 2 CH 2 NH 2 )] n ( 12 ). Treatment of polyferrocenylsilanes 11 and 12 with HCl generated the water-soluble cationic polyelectrolytes [fcSiMe(C⋮CCH 2 NH 3 Cl)] n ( 13 ) and [fcSiMe(CH 2 CH 2 CH 2 NH 3 Cl)] n ( 14 ), respectively. Cationic polyferrocenylsilanes 13 and 14 were obtained in three steps from polymer 3 with an overall yield of 40−50%. An unexpected rearrangement process took place during the lithiation of the protected aminopropyl bromide Br(CH 2 ) 3 N(SiMe 2 CH 2 ) 2 ( 15 ) and a reaction of the resulting lithium salt with 6 yielded the novel [1]ferrocenophane fcSiMe{N(CH 2 ) 3 SiMe 2 (CH 2 ) 2 SiMe 2 } ( 17 ) with a rearranged, and ring-expanded, cyclic silylamino substituent. Species 17 underwent thermal ring-opening polymerization to afford [fcSiMe{N(CH 2 ) 3 SiMe 2 (CH 2 ) 2 SiMe 2 }] n ( 18 ). Treatment of polymer 10 with 1,3-propane sultone afforded the anionic polyelectrolyte [fcSiMe{C⋮CCH 2 N(CH 2 CH 2 CH 2 SO 3 Na) 2 }] n ( 19 ). Polymer 19 was readily reduced with hydrazine to give [fcSiMe{CH 2 CH 2 CH 2 NH(CH 2 CH 2 CH 2 SO 3 )(CH 2 CH 2 CH 2 SO 3 Na)}] n ( 20 ) bearing saturated side chains; subsequent deprotonation yielded the anionic polyelectrolyte [fcSiMe{CH 2 CH 2 CH 2 N(CH 2 CH 2 CH 2 SO 3 Na) 2 }] n ( 21 ). All three anionic polyelectrolytes 19 − 21 were obtained in 2−3 steps from 3 with 60−75% overall yields. The polyferrocenylsilane polyelectrolytes 13, 14, and 19 − 21 were readily soluble in water, making them potentially useful materials for a range of applications.

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Full frame distilled prediction

Teacher imitation

Not 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.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.005
Threshold uncertainty score0.498

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

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.

Opus teacher head0.011
GPT teacher head0.219
Teacher spread0.208 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it