Polymerization of optically active 2-fluorophenyl-4-fluorophenyl-2-pyridylmethyl methacrylate with anionic and radical initiators: Stereospecificity and helix-sense selection

Wu, Jian

doi:10.1002/(sici)1099-0518(19990715)37:14<2645::aid-pola39>3.0.co;2-7

Cited by 19 publications

(13 citation statements)

References 9 publications

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“…301 A similar tendency was observed for the polymerization of another chiral and bulky methacrylate with fluorinated substituents (CM-13). 302 Furthermore, the introduction of a chiral auxiliary into the ethylene-linkage of PDBSMA (CM-14) resulted in the self-induction of the prevailing one-handed helicity without loss of the highly isotactic specificity. 303 Since the report by Wulff et al that the asymmetric cyclopolymerization of distyryl monomers with a chiral linkage (CM-15) resulted in main-chain chiral polymers, various divinyl monomers with a chiral template were intensivelystudiedmainlyinordertoobtainchiralpolymers.…”

Section: Monomers With Chiral Auxiliarymentioning

confidence: 99%

Stereospecific Living Radical Polymerization: Dual Control of Chain Length and Tacticity for Precision Polymer Synthesis

2009

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Section: Monomers With Chiral Auxiliarymentioning

confidence: 99%

Stereospecific Living Radical Polymerization: Dual Control of Chain Length and Tacticity for Precision Polymer Synthesis

2009

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“…The stereochemistry of 2F4F2PyMA whose structure was similar to PPyoTMA was also investigated 32,33) Although most of the bulky methacrylates described so far give isotactic polymers by radical polymerization as well as by anionic polymerization at low temperatures, the isotactic specificity of radical polymerization is generally lower than that in anionic polymerization. However, 1phenyldibenzosuberyl methacrylate (PDBS-MA) [18][19][20] and its derivatives (2PyDBSMA and 3PyDBSMA) 17,25) afford nearly completely isotactic polymers by radical polymerization regardless of the reaction condition.…”

Section: Free-radical Polymerization Of Bulky Methacrylatesmentioning

confidence: 99%

Asymmetric polymerization of methacrylates

Nakano,

Okamoto

2000

Macromol. Rapid Commun.

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The syntheses of optically active polymers having helical conformation from bulky methacrylates are reviewed focusing on selected topics. The monomers include triphenylmethyl methacrylate and its analogues. Asymmetric anionic polymerization of the monomers gives isotactic, optically active polymers having a helical structure with excess helicity. The isotactic content and the extent of helical‐sense excess depend on the monomer structure and the reaction conditions. In the case of methacrylates, completely isotactic and single‐handed helical polymers can be produced by asymmetric anionic polymerization (helix‐sense‐selective polymerization). Asymmetric radical polymerization is also possible for this class of monomer. Some of the helical polymers show chiral recognition ability toward a wide range of racemic compounds. Polymers having main‐chain configurational chirality are also discussed.

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“…Okamoto and coworkers first achieved the synthesis of one‐handed helical vinyl polymers via radical polymerization of bulky methacrylates 34–41. Such chiral induction can be fulfilled by either the chirality of a monomer itself or a chiral additive acting as a spectator to the polymerization process.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of optically active helical vinyl polymers via free radical polymerization

Zhi

Guan

Cui

et al. 2009

J. Polym. Sci. A Polym. Chem.

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A facile synthetic route to prepare the dual-functional molecule, 2,5bis(4 0 -carboxyphenyl)styrene, was developed. The esterification of this compound with chiral alcohols, that is, (S)-(þ)-sec-butanol/(R)-(À)-sec-butanol, (S)-(þ)-secoctanol/(R)-(À)-sec-octanol, and D-(þ)-menthol/L-(À)-menthol, respectively, yielded three enantiomeric pairs of novel vinyl monomers, which underwent radical polymerization to obtain helical polymers with an excess screw sense. These polymers exhibited optical rotations as large as fourfold those of the corresponding monomers. Their helical conformations were quite stable as revealed by the almost unchanged chiroptical properties measured at different temperatures. The polymers with linear alkyl tails in the side-groups formed irreversibly columnar nematic phases in melt although the corresponding monomers were not liquid crystalline. Whereas, the polymers with cyclic tails generated no mesophase.

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Polymerization of optically active 2-fluorophenyl-4-fluorophenyl-2-pyridylmethyl methacrylate with anionic and radical initiators: Stereospecificity and helix-sense selection

Cited by 19 publications

References 9 publications

Stereospecific Living Radical Polymerization: Dual Control of Chain Length and Tacticity for Precision Polymer Synthesis

Stereospecific Living Radical Polymerization: Dual Control of Chain Length and Tacticity for Precision Polymer Synthesis

Asymmetric polymerization of methacrylates

Synthesis and characterization of optically active helical vinyl polymers via free radical polymerization

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