Anionic polymerization initiators containing protected functional groups and functionally terminated diene polymers

Schulz, D. N.; Halasa, Adel F.; Oberster, A. E.

doi:10.1002/pol.1974.170120114

Cited by 51 publications

(18 citation statements)

References 18 publications

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“…Although such macromonomer can also be synthesized through the tandem anionic polymerization of St and ethylene oxide with a hydroxyl‐protected organolithium reagent as an initiator following acidic hydrolysis and esterification with methacryloyl chloride,46 the process may be more inconvenient. Mendrek et al47 synthesized an amphiphilic macromonomer containing a polymerizable St head group and a tail of ethylene oxide derivatives of different character.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of well‐defined macromonomers by the combination of atom transfer radical polymerization and a click reaction

Liu

Chen

2006

J. Polym. Sci. A Polym. Chem.

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This article presents a new strategy for synthesizing a series of welldefined macromonomers. Bromine-terminated polystyrene and poly(t-butyl acrylate) with predetermined molecular weights and narrow distributions were prepared through the atom transfer radical polymerization of styrene and t-butyl acrylate initiated with ethyl 2-bromoisobutyrate. Then, azido-terminated polymers were obtained through the bromine substitution reaction with sodium azide. Catalyzed by CuBr/ N,N,N 0 ,N 00 ,N 00 -pentamethyldiethylenetriamine, the azido end group reacted with propargyl methacrylate via a 1,3-dipolar cycloaddition reaction, and x-methacryloylfunctionalized macromonomers were thus obtained. The end-group transformation yields were rather high, as characterized by matrix-assisted laser desorption/ionization time-of-flight mass spectra and 1 H NMR analysis. By this effective and facile approach, some novel macromonomers that otherwise are difficult to achieve, such as poly(ethylene oxide)-block-polystyrene, were easily prepared. Radical homopolymerizations of these macromonomers were performed, and a series of comb polymers were prepared. V V C 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: [6103][6104][6105][6106][6107][6108][6109][6110][6111][6112][6113] 2006

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Section: Resultsmentioning

confidence: 99%

Synthesis of well‐defined macromonomers by the combination of atom transfer radical polymerization and a click reaction

Liu

Chen

2006

J. Polym. Sci. A Polym. Chem.

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“…[8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] This limitation can be in part avoided by the use of functionally substituted DPE derivatives coupled with organolithium compounds. It is also advantageous that many substituted DPE derivatives with several anion-stable functional groups have been synthesized especially in recent years.…”

Section: Resultsmentioning

confidence: 99%

New Functionalized Anionic Initiators Prepared from Substituted 1,1‐Diphenylethylene Derivatives with Acetal‐Protected Monosaccharides and Their Application to Chain‐Multi‐Functionalized Polymers with Glucose and Galactose Molecules

Loykulnant

Hirao

2003

Macro Chemistry & Physics

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Living anionic polymerizations of methyl methacrylate, tert‐butyl methacrylate, 2‐(perfluorobutyl)ethyl methacrylate, tert‐butyl acrylate, and ethylene oxide were carried out with functionalized initiators prepared from substituted 1,1‐diphenylethylene (DPE) derivatives with two and four acetal‐protected α‐D‐glucofuranose and α‐D‐galactopyranose residues and carbanionic species such as sec‐butyllithium (sec‐BuLi), cumylpotassium, lithium and potassium naphthalenides. In certain cases, either LiCl or diethylzinc was used as an additive to control the polymerization. Several new well‐defined chain‐end‐ and in‐chain‐functionalized polymers with two and four glucose and two galactose molecules were successfully synthesized by these living polymerizations followed by deprotection. We have proposed a promising iterative methodology based on a convergent approach, with which novel two dendritic substituted DPE derivatives with four and eight acetal‐protected D‐glucofuranose residues can successively be synthesized. With use of the functionalized anionic initiators prepared from such dendritic DPE derivatives and sec‐BuLi in the polymerization of methyl methacrylate, well‐defined chain‐end‐functionalized poly(methyl methacrylate)s with four and eight glucose molecules were synthesized.magnified image

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“…More than 20 years ago, Schulz and his coworkers were the first to introduce a protective group in the synthesis and use of the anionic functionalized initiator [32]. They synthesized two organolithium initiators with acetal-protected hydroxy functionalities 18 and 19 as shown in Fig.…”

Section: Synthesis Of End-functionalized Polymers With Use Of Functiomentioning

confidence: 98%

Recent advance in syntheses and applications of well-defined end-functionalized polymers by means of anionic living polymerization

Hirao¹,

Hayashi

1999

Acta Polym.

112

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Anionic polymerization initiators containing protected functional groups and functionally terminated diene polymers

Cited by 51 publications

References 18 publications

Synthesis of well‐defined macromonomers by the combination of atom transfer radical polymerization and a click reaction

Synthesis of well‐defined macromonomers by the combination of atom transfer radical polymerization and a click reaction

New Functionalized Anionic Initiators Prepared from Substituted 1,1‐Diphenylethylene Derivatives with Acetal‐Protected Monosaccharides and Their Application to Chain‐Multi‐Functionalized Polymers with Glucose and Galactose Molecules

Recent advance in syntheses and applications of well-defined end-functionalized polymers by means of anionic living polymerization

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