2004
DOI: 10.1295/polymj.36.728
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Novel Initiating System for the Stereocontrolled Radical Polymerization of Acrylamides: Alkyl Bromide/Rare Earth Metal Triflate System

Abstract: ABSTRACT:A novel radical initiating system -rare-earth metal triflate [Y(OTf) 3 , Yb(OTf) 3 , Lu(OTf) 3 , Sc(OTf) 3 ] and alkyl halide containing -esters (ethyl 2-bromoisobutyrate and ethyl 2-bromopropionate) or -amide (N,N-dimethyl-2-bromo-2-methylpropanamide) was used for the stereocontrolled radical polymerization of N-isopropylacrylamide (NIPAM). The Lewis acids serve a dual role as the promoter of the radical initiation and the controller of the stereospecific polymerization. The effects of the Lewis acid… Show more

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Cited by 23 publications
(8 citation statements)
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“…Alternatively, the interaction between KBr and FeBr3, yielding K[FeBr4] may enhance the Lewis acidity of K + , resulting in the same homolytic C-Br bond labilisation. 39 The second experiment, using KOH, leads to the GC trace shown in Figure 9.2. In this case, the activation is very efficient, leaving no residual EBrPA after the 2 h heating period.…”
Section: (E) Mechanistic Studiesmentioning
confidence: 99%
“…Alternatively, the interaction between KBr and FeBr3, yielding K[FeBr4] may enhance the Lewis acidity of K + , resulting in the same homolytic C-Br bond labilisation. 39 The second experiment, using KOH, leads to the GC trace shown in Figure 9.2. In this case, the activation is very efficient, leaving no residual EBrPA after the 2 h heating period.…”
Section: (E) Mechanistic Studiesmentioning
confidence: 99%
“…Controlled-living radical polymerization, especially reversible addition-fragmentation chain-transfer (RAFT) polymerization, provides the benefit of being able to readily synthesize polymers with predetermined molecular structures and narrow molecular weight distributions [28,29,30,31]. In addition, RAFT polymerization can be applied to bulk, solution, emulsion or suspension polymerizations.…”
Section: Introductionmentioning
confidence: 99%
“…Thiocarbonylthio compounds, including dithoester and trithiocarbonate, are commonly used as RAFT agents. The addition of Lewis acid during polymerization can affect the stereochemistry of the polymers [19,29,30,31].…”
Section: Introductionmentioning
confidence: 99%
“…Living radical polymerization methods, such as atom transfer radical polymerization (ATRP) , and reversible addition–fragmentation chain transfer (RAFT), , are effective in controlling block copolymers, but have yet to show the capability in affecting the stereochemistry of the polymers. Stereoselective polymerization based on the chain polymerization mechanism has been attempted by using auxiliaries, such as metal triflates, to introduce stereoselectivity into the chain-propagating site. , Nevertheless, the use of strongly associative metal triflates calls for an addition purification step in the postpolymerization treatment. Recently, stereoregular polymers have been synthesized by utilizing hydrogen bonding rather than coordination to an organotransition metal complex to sterically control the reactive radical sites .…”
Section: Introductionmentioning
confidence: 99%