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Journal of the American Chemical Society
Volumn 131, Issue 19, 2009, Pages 6708-6718
Enantiomer-selective and helix-sense-selective living block copolymerization of isocyanide enantiomers initiated by single-handed helical poly(phenyl isocyanide)s
Author keywords

[No Author keywords available]
Indexed keywords

ATOMIC FORCE MICROSCOPY; BLOCK COPOLYMERS; CHIRALITY; CYANIDES; DICHROISM; ENANTIOMERS; LIQUID CRYSTAL POLYMERS; LIVING POLYMERIZATION; MOLECULAR WEIGHT DISTRIBUTION; PALLADIUM; PLATINUM;
EID: 67650519810     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja900036n     Document Type: Article
Times cited : (136)
References (116)
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    • A similar helixsense-selective cyclization polymerization of achiral 1,2-diisocyanobenzenes using a single-handed helical oligomer as an initiator was reported, see
    • A similar helixsense-selective cyclization polymerization of achiral 1,2-diisocyanobenzenes using a single-handed helical oligomer as an initiator was reported, see: (c) Ito, Y.; Ihara, E.; Murakami, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 1509-1510.
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    • The helical sense (P or M) and helical sense excess (>97%) of the M-poly-L-1(-) and P-poly-L-1(+) were directly determined by high-resolution AFM observations.9
    • The helical sense (P or M) and helical sense excess (>97%) of the M-poly-L-1(-) and P-poly-L-1(+) were directly determined by high-resolution AFM observations.9
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    • A similar enantiomer-selective anionic polymerization of racemic phenyl-2-pyridyl-o-tolylmethyl methacrylate (PPyTMA) was performed using the preformed living poly(PPyTMA) with a one-handed helical conformation as the initiator, whose enantiomer selectivity was governed by the rigid helical structure of the growing polymer chain. See
    • A similar enantiomer-selective anionic polymerization of racemic phenyl-2-pyridyl-o-tolylmethyl methacrylate (PPyTMA) was performed using the preformed living poly(PPyTMA) with a one-handed helical conformation as the initiator, whose enantiomer selectivity was governed by the rigid helical structure of the growing polymer chain. See: (a) Yashima, E.; Okamoto, Y.; Hatada, K. Macromolecules 1988, 21, 854-855.
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    • For reviews on helical polyisocyanides, see refs 1b and 1h, and
    • For reviews on helical polyisocyanides, see refs 1b and 1h, and: (a) Millich, F. Chem. Rev. 1972, 72, 101-113.
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    • For other leading references of helical polyisocyanides, see
    • For other leading references of helical polyisocyanides, see: (g) Kamer, P. C. J.; Nolte, R. J. M.; Drenth, W. J. Am. Chem. Soc. 1988, 110, 6818-6825.
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    • We recently reported the unprecedented helix-sense controlled polymerization of L-1. The polymerization of L-1 with an achiral nickel catalyst diastereoselectively proceeded, resulting in either right- or left-handed helical poly-L-1, whose helix-sense was controlled by the polymerization solvent and temperature
    • We recently reported the unprecedented helix-sense controlled polymerization of L-1. The polymerization of L-1 with an achiral nickel catalyst diastereoselectively proceeded, resulting in either right- or left-handed helical poly-L-1, whose helix-sense was controlled by the polymerization solvent and temperature: (a) Kajitani, T.; Okoshi, K.; Sakurai, S.-i.; Kumaki, J.; Yashima, E. J. Am. Chem. Soc. 2006, 128, 708-709.
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    • Similar diastereomeric helical polyisocyanides were also prepared by the copolymerization between achiral and chiral isocyanides or two different chiral isocyanides based on the selective growth inhibition of a one screw-sense. See refs 14g and 14l
    • (b) Kajitani, T.; Okoshi, K.; Yashima, E. Macromolecules 2008, 41, 1601-1611, Similar diastereomeric helical polyisocyanides were also prepared by the copolymerization between achiral and chiral isocyanides or two different chiral isocyanides based on the selective growth inhibition of a one screw-sense. See refs 14g and 14l.
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    • The CD spectral patterns and intensities of polyisocyanides measured in CHCl3 (Figure 4A) were almost identical to those in THF
    • The CD spectral patterns and intensities of polyisocyanides measured in CHCl3 (Figure 4A) were almost identical to those in THF.
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    • For helix-sense-selective polymerization of achiral bulky isocyanides with chiral initiators or catalysts, see refs 1b, 1h, 14e, and 14g, and
    • For helix-sense-selective polymerization of achiral bulky isocyanides with chiral initiators or catalysts, see refs 1b, 1h, 14e, and 14g, and: (a) Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926-7927.
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    • For helix-sense-selective block copolymerization of achiral isocyanides or chiral isocyanides using optically active polyisocyanide prepolymers as initiators, see refs 10a-c. For helix-sense-selective and enantiomer-selective block copolymerization of chiral isocyanides using optically active polyisocyanide prepolymers as initiators, see
    • For helix-sense-selective block copolymerization of achiral isocyanides or chiral isocyanides using optically active polyisocyanide prepolymers as initiators, see refs 10a-c. For helix-sense-selective and enantiomer-selective block copolymerization of chiral isocyanides using optically active polyisocyanide prepolymers as initiators, see: (b) Metselaar, G. A.; Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M. Angew. Chem., Int. Ed. 2005, 44, 1990-1993.
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    • For leading references of helix-sense-selective polymerization of other achiral monomers using chiral initiators or catalysts: Methacrylates, 1a,g,4c
    • For leading references of helix-sense-selective polymerization of other achiral monomers using chiral initiators or catalysts: Methacrylates, 1a,g,4c (c) Okamoto, Y.; Suzuki, K.; Ohta, K.; Hatada, K.; Yuki, H. J. Am. Chem. Soc. 1979, 101, 4763-4765.
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    • The living polyisocyanides prepared by the μ-ethynediyl Pt-Pd catalyst (2) are thermally stable in solution at 55°C for 24 h and in the solid state at least for a year and maintain its polymerization activity
    • The living polyisocyanides prepared by the μ-ethynediyl Pt-Pd catalyst (2) are thermally stable in solution at 55°C for 24 h and in the solid state at least for a year and maintain its polymerization activity.
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    • The AFM images of larger areas (Figure S6) revealed that the left-handed helical M-poly-L-1100(-)-b-D-1 (d in Figure S6) is composed of very few opposite right-handed helical segments, which agreed with a slight decrease in its CD intensity (Table 1)
    • The AFM images of larger areas (Figure S6) revealed that the left-handed helical M-poly-L-1100(-)-b-D-1 (d in Figure S6) is composed of very few opposite right-handed helical segments, which agreed with a slight decrease in its CD intensity (Table 1).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.