Synthesis and structure determination of helical polymers

Polymer Journal

Volumn 42, Issue 1, 2010, Pages 3-16

  Yashima, Eiji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Atomic force microscopy; Circular dichroism; Helical polymer; Helical structure; X ray diffraction

Indexed keywords

ATOMIC FORCE; CIRCULAR DICHROISM; HELICAL PITCH; HELICAL POLYMERS; HELICAL SENSE; HELICAL STRUCTURES; HIGH RESOLUTION; RECENT PROGRESS; SPECTROSCOPIC MEASUREMENTS; STRUCTURAL DETERMINATION; STRUCTURE DETERMINATION; SYNTHETIC HELICAL POLYMERS;

ATOMIC FORCE MICROSCOPY; ATOMIC SPECTROSCOPY; ATOMS; DIFFRACTION; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

DICHROISM;

EID: 74049090386     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1038/pj.2009.314     Document Type: Review

References (98)

1. Okamoto, Y. & Nakano, T. Asymmetric polymerization. Chem. Rev. 94, 349-372 (1994).
2. Pu, L. The study of chiral conjugated polymers. Acta Polym. 48, 116-141 (1997).
3. Rowan, A. E. & Nolte, R. J. M. Helical molecular programming. Angew. Chem., Int. Ed. 37, 63-68 (1998).
4. Nakano, T. & Okamoto, Y. Synthetic helical polymers: conformation and function. Chem. Rev. 101, 4013-4038 (2001).
5. Comelissen, J. J. L. M., Rowan, A. E., Nolte, R. J. M. & Sommerdijk, N. A. J. M. Chiral architectures from macromolecular building blocks. Chem. Rev. 101, 4039-4070 (2001).
6. Green, M. M., Peterson, N. C., Sato, T., Teramoto, A., Cook, R. & Lifson, S. A helical polymer with a cooperative response to chiral information. Science 268, 1860-1866 (1995).
7. Fujiki, M. Optically active polysilylenes: state-of-the-art chiroptical polymers. Macromol. Rapid Commun. 22, 539-563 (2001).
8. Nomura, R., Nakako, H. & Masuda, T. Design and synthesis of semiflexible substituted polyacetylenes with helical conformation. J. Mol. Catal. A: Chem. 190, 197-205 (2002). (Pubitemid 35364568)
9. Maeda, K. & Yashima, E. Dynamic helical structures: detection and amplification of chirailty. Top. Curr. Chem. 265, 47-88 (2006). (Pubitemid 44420761)
10. Rudick, J. G. & Percec, V. Induced helical backbone conformations of self-organizable dendronized polymers. Acc. Chem. Res. 41, 1641-1652 (2008).
11. Yashima, E. & Maeda, K. Chirality-responsive helical polymers. Macromolecules 41, 3-12 (2008).
12. Yashima, E., Maeda, K. & Furusho, Y. Single- and double-stranded helical polymers: synthesis, structures, and functions. Acc. Chem. Res. 41, 1166-1180 (2008).
13. Pino, P. & Lorenzi, G. P. Optically active vinyl polymers. II. The optical activity of isotactic and block polymers of optically active α-olefins in dilute hydrocarbon solution. J. Am. Chem. Soc. 82, 4745-4747 (1960).
14. Green, M. M. & Jha, S. K. The road to chiral amplification in polymers originated in Italy. Chirality9, 424-427 (1997).
15. Nolte, R. J. M., Van Beijnen, A. J. M. & Drenth, W. Chirality In polyisocyanides. J. Am. Chem. Soc. 96, 5932-5933 (1974).
16. Okamoto, Y., Suzuki, K., Ohta, K., Hatada, K. & Yuki, H. Optically active poly(triphenylmethyl methacrylate) with one-handed helical conformation. J. Am. Chem. Soc. 101, 4763-4765 (1979).
17. Green, M. M., Andreola, C., Munoz, B., Reidy, M. P. & Zero, K. Macromolecular stereochemistry: a cooperative deuterium isotope effect leading to a large optical rotation. J. Am. Chem. Soc. 110, 4063-4065 (1988).
18. Corley, L. S. & Vogl, O. Optically active polychloral. Polym. Bull. 3, 211-217 (1980).
19. Fujiki, M. Ideal exciton spectra in single- and double-screw-sense helical polysilanes. J. Am. Chem. Soc. 116, 6017-6018 (1994). (Pubitemid 24981232)
20. Green, M. M., Reidy, M. P., Johnson, R. J., Darling, G., Oleary, D. J. & Willson, G. Macromolecular stereochemistry: the out-of-proportion influence of optically active comonomers on the conformational characteristics of polyisocyanates. the sergeants and soldiers experiment. J. Am. Chem. Soc. 111, 6452-6454 (1989).
21. Green, M. M., Garetz, B. A., Munoz, B., Chang, H. P., Hoke, S. & Cooks, R. G. Majority rules In the copolymerization of mirror-image isomers. J. Am. Chem. Soc. 117, 4181-4182(1995).
22. Maeda, K. & Okamoto, Y. Helical structure of oligo- and poly(m-substituted phenyl isocyanate)s bearing an optically active end-group. Pol. J. 30, 100-105 (1998).
23. Inal, Y., Tagawa, K., Takasu, A., Hirabayashi, T., Oshikawa, T. & Yamashita, M. Induction of one-handed helical screw sense In achira peptide through the domino effect based on interacting its n-terminal amino group with chiral carboxylic acid. J. Am. Chem. Soc. 122, 11731-11732 (2000).
24. Yashima, E., Matsushima, T. & Okamoto, Y. Poly((4-carboxyphenyl) acetylene) as a probe for chirality assignment of amines by circular dichroism. J. Am. Chem. Soc. 117, 11596-11597(1995).
25. Suginome, M. & Ito, Y. Transition metal-mediated polymerization of isocyanides. Adv. Polym. Sci. 17, 77-136 (2004).
26. Ito, Y., Kojima, Y., Murakami, M. & Suginome, M. Racemization and deracemization of poly (quinoxaline-2,3-diyl)s. Bull. Chem. Soc. Jpn. 70, 2801-2806 (1997).
27. Schlitzer, D. S. & Novak, B. M. Trapped kinetic states, chiral amplification and molecular chaperoning in synthetic polymers: chiral induction in polyguanidines through ion pair interactions. J. Am. Chem. Soc. 120, 2196-2197 (1998).
28. Tang, H. Z., Lu, Y. J., Tian, G. L., Capracotta, M. D. & Novak, B. M. Stable helical polyguanidines: poly\{N-(1-anthryl)-N′-[(R)- and/or (S)-3, 7-dimethyloctyl]guanidines. J. Am. Chem. Soc. 126, 3722-3723 (2004).
29. Ishikawa, M., Maeda, K. & Yashima, E. Macromolecular chirality induction on optically inactive poly (4-carboxyphenyl isocyanide) with chiral amines: a dynamic conformational transition of poly(phenyl isocyanide) derivatives. J. Am. Chem. Soc. 124, 7448-7458 (2002).
30. Ishikawa, M., Maeda, K., Mltsutsuji, Y. & Yashima, E. An unprecedented memory of macromolecular helicity induced in an achiral polyisocyanide in water. J. Am. Chem. Soc. 126, 732-733 (2004).
31. Lam, J. W. Y. & Tang, B. Z. Functional polyacetylenes. Acc. Chem. Res. 38, 745-754 (2005).
32. Nomura, R., Fukushima, Y., Nakako, H. & Masuda, T. Conformational Study of Helical Poly(propiolic esters) in Solution. J. Am. Chem. Soc. 122, 8830-8836 (2000).
33. Aoki, T., Kaneko, T., Maruyama, N., Sumi, A., Takahashi, M., Sato, T. & Teraguchi, M Helix-sense-selective polymerization of phenylacetylene having two hydroxy groups using a chiral catalytic system. J. Am. Chem. Soc. 125, 6346-6347 (2003).
34. Rudick, J. G. & Percec, V. Nanomechanical function made possible by suppressing structural transformations of polyarylacetylenes. Macromol. Chem. Phys. 209, 1759-1768(2008).
35. Yashima, E., Maeda, K. & Okamoto, Y. Memory of macromolecular helicity assisted by interaction with achiral small molecules. Nature 399, 449-451 (1999). (Pubitemid 29258846)
36. Pauling, L. & Corey, R. B. The structure of synthetic polypeptides. Proc. Natl. Acad. Sci. USA 37, 241-250 (1951).
37. Watson, J. D. & Crick, F. H. C. Molecular structure of nucleic acids: a structure for deoxyribose nucleic acid. Nature 171, 737-738 (1953).
38. Shmueli, U., Traub, W. & Rosenheck, K. Structure of Poly(N-butyl isocyanate). J. Polym. Sci., Part A-2: Polym. Phys. 7, 515-524 (1969).
39. Miller, R. D., Farmer, B. L., Fleming, W., Sooriyakumaran, R. & Rabolt, J. Poly(di-n-pentylsilane). The spectral consequences of a helical conformation in the solid state. J. Am. Chem. Soc. 109, 2509-2510 (1987).
40. Watanabe, J., Kamee, H. & Fujiki, M. First observation of thermotropic cholesteric liquid crystal in helical polysilane. Pol. J. 33, 495-497 (2001).
41. Schlüter, A. D. & Rabe, J. P. Dendronized polymers: synthesis, characterization, assembly at interfaces, and manipulation. Angew. Chem., Int. Ed. 39, 864-883 (2000).
42. Sheiko, S. S. & Moller, M. Visualization of macromolecules a first step to manipulation and controlled response. Chem. Rev. 101, 4099-4124 (2001). (Pubitemid 35373054)
43. Kumaki, J., Sakurai, S.-i. & Yashima, E. Visualization of synthetic helical polymers by high-resolution atomic force microscopy. Chem. Soc. Rev. 38, 737-746 (2009).
44. Vogl, O., Jaycox, G. D., Kratky, C., Simonsick, W. J. & Hatada, K. Mapping the genesis of helical structure in polymers of the trihaloacetaldehydes. Acc. Chem. Res. 25, 408-413 (1992).
45. Ute, K., Hirose, K., Kashimoto, H., Nakayama, H., Hatada, K. & Vogl, O. Helix-inversion equlibrium of isotactic chloral oligomers in solution. Pol. J. 25, 1175-1186 (1993).
46. Ute, K., Hirose, K., Kashimoto, H., Hatada, K. & Vogl, O. Haloaldehyde polymers. 51. Helix-sense reversal of isotactic chloral oligomers In solution. J. Am. Chem. Soc. 113, 6305-6306 (1991).
47. Ute, K., Fukunishi, Y., Niimí, R., Iwakura, T. & Hatada, K. Helical structure in solution and in the crystalline state of uniform polyisocyanates obtained by supercritical fluid chromatography. Polym. Prep. Jpn. 45, 3284-3285 (1996).
48. Ito, Y., Ohara, T., Shíma, R. & Suginome, M. Highly screw-sense selective polymerization of 1, 2-diisocyano-3, 6-di-p-tolylbenzene initiated by optically active binaphthylpalladium(ii) complexes. J. Am. Chem. Soc. 118, 9188-9189 (1996). (Pubitemid 26342562)
49. Tanatani, A., Yokoyama, A., Azumaya, I., Takakura, Y., Mitsui, C., Shiro, M., Uchiyama, M, Muranaka, A, Kobayashi, N & Yokozawa, T Helical structures of N-Alkylated Poly(pbenzamlde)s. J. Am. Chem. Soc. 127, 8553-8561 (2005).
50. Aharoni, S. M. Rigid backbone polymers. 2. Polyisocyanates and their liquid-crystal behavior. Macromolecules 12, 94-103 (1979).
51. Millich, F. Rigid rod-random coil transformation, mark-houwink constants, and millich's intrinsic isoviscoslty, [η]M, and Isohydrodynamlc volume, [η]MMM. Adv. Polym. Sci. 19, 117-141 (1975).
52. Aharoni, S. M. Rigid backbone polymers. I. Polyisocyanides. J. Polym. Sci.: Polym. Phys. Ed. 17, 683-691 (1979).
53. Yashima, E., Maeda, K., Iida, H., Furusho, Y. & Nagai, K. Helical polymers: synthesis, structures and functions. Chem. Rev. 109, 6102-6211 (2009).
54. Maeda, K., Takeyama, Y., Sakajiri, K. & Yashima, E. Nonracemic dopant-mediated hierarchical amplification of macromolecular helicity in a charged polyacetylene leading to a cholesteric liquid crystal in water. J. Am. Chem. Soc. 126, 16284-16285 (2004).
55. Nagai, K., Sakajiri, K., Maeda, K., Okoshi, K., Sato, T. & Yashima, E. Hierarchical amplification of macromolecular helicity in a lyotropic liquid crystalline charged Poly(phenylacetylene) by nonracemic dopants in water and its helical structure. Macromolecules 39, 5371-5380 (2006). (Pubitemid 44325116)
56. Okoshi, K., Sakurai, S.-i., Ohsawa, S., Kuniaki, J. & Yashima, E. Control of main-chain stiffness of a helical poly(phenylacetylene) by switching on and off the intramolecular hydrogen bonding through macromolecular helicity inversion. Angew. Chem., Int. Ed. 45, 8173-8176 (2006).
57. Okoshi, K., Kajitani, T., Nagai, K. & Yashima, E. Uniaxial orientation of a rodlike helical poly(phenylacetylene) in an electric field. Macromolecules41, 258-261 (2008).
58. Yen, C.- C., Tokita, M., Park, B., Takezoe, H. & Watanabe, J. Spontaneous organization of helical polypeptide molecules into polar packing structure. Macromolecules 39, 1313-1315 (2006).
59. Okoshi, K., Nagai, K., Kajitani, T., Sakurai, S.-i. & Yashima, E. Anomalous stiff backbones of helical poly(phenyl isocyanide) derivatives. Macromolecules 41, 7752-7754 (2008).
60. Sato, T. & Teramoto, A. Concentrated solutions of liquid-crystalline polymers. Adv. Polym. Sci. 126, 85-161 (1996).
61. Yashima, E., Matsushima, T. & Okamoto, Y. Chirality assignment of amines and amino alcohols based on circular dichroism induced by helix formation of a stereoregular poly((4-carboxyphenyl)acetylene) through acid-base complexatlon. J. Am. Chem. Soc. 119, 6345-6359 (1997).
62. Goto, H., Zhang, H. Q. & Yashima, E. Chiral stimuli-responsive gels: helicity induction in poly (phenylacetylene) gels bearing a carboxyl group with chiral amines. J. Am. Chem. Soc. 125, 2516-2523 (2003). (Pubitemid 36512238)
63. Onouchi, H., Maeda, K. & Yashima, E. A Helical Polyelectrolyte Induced by Specific Interactions with Biomolecules in Water. J. Am. Chem. Soc. 123, 7441-7442 (2001).
64. Onouchi, H., Hasegawa, T., Kashiwagi, D., Ishiguro, H., Maeda, K. & Yashima, E. Helicity induction in charged poly(phenylacetylene)s bearing various acidic functional groups in water and its mechanism. Macromolecules 38, 8625-8633 (2005).
65. Onouchi, H., Hasegawa, T., Kashiwagi, D., Ishiguro, H., Maeda, K. & Yashima, E. Chirality Sensing of Various Biomolecules with Helical Poly(phenylacetylene)s Bearing Acidic Functional Groups in Water. J. Polym. Sci., Part A: Polym. Chem. 44, 5039-5048 (2006). (Pubitemid 44368582)
66. Hasegawa, T., Maeda, K., Ishiguro, H. & Yashima, E. Helicity induction on a poly(phenylacetylene) derivative bearing a sulfonic acid pendant with chiral amines and memory of the macromolecular helicity in dimethyl sulfoxide. Pol. J. 38, 912-919 (2006). (Pubitemid 44719779)
67. Onouchi, H., Kashiwagi, D., Hayashi, K., Maeda, K. & Yashima, E. Helicity induction on poly(phenylacetylene)s bearing phosphonlc acid pendants with chiral amines and memory of the macromolecular helicity assisted by interaction with achiral amines in dimethyl sulfoxide. Macromolecules 37, 5495-5503 (2004).
68. Maeda, K., Morino, K., Okamoto, Y., Sato, T. & Yashima, E. Mechanism of Helix induction on a stereoregular poly((4-carboxyphenyl)acetylene) with chiral amines and memory of the macromolecular helicity assisted by interaction with achiral amines. J. Am. Chem. Soc. 126, 4329-4342 (2004).
69. Hase, Y., Nagai, K., Iida, H., Maeda, K., Ochi, N., Sawabe, K., Sakajiri, K, Okoshi, K & Yashima, E Mechanism of Helix induction in poly(4-carboxyphenyl isocyanide) with chiral amines and memory of the macromolecular helicity and its helical structures. J. Am. Chem. Soc. 131, 10719-10732 (2009).
70. Hase, Y., Mitsutsuji, Y., Ishikawa, M., Maeda, K., Okoshi, K. & Yashima, E. Unexpected thermally stable, cholesteric liquid-crystalline helical polyisocyanides with memory of macromolecular helicity. Chem. Asian J. 2, 755-763 (2007).
71. Miyabe, T., Hase, Y, Iida, H., Maeda, K. & Yashima, E. Synthesis of functional poiy(phenyl isocyanide)s with macromolecular helicity memory and their use as asymmetric organocatalysts. Chirality 21, 44-50 (2009).
72. Harada, N. & Nakanishi, K. Circular Dichroic Spectroscopy-Exeiton Coupling in Organic Stereochemistry, (University Science Book, Mill Valley, CA, 1983).
73. Takei, F., Hayashi, H., Onitsuka, K., Kobayashi, N. & Takahashi, S. Helical chiral polyisocyanides possessing porphyrin pendants: determination of helicity by excitoncoupled circular dichroism. Angew. Chem., Int. Ed. 40, 4092-4094 (2001).
74. Tabei, J., Shiotsuki, M., Sanda, F. & Masuda, T. Determination of helical sense of poly(N-propargylamides) by exciton-coupled circular dichroism. Macromolecules 38, 9448-9454 (2005).
75. Cornelissen, J. J. L. M., Sommerdijk, N.A.J. M. & Nolte, R. J. M. Determination of the helical sense in alanine based polyisocyanides. Macromol. Chem. Phys. 203, 1625-1630 (2002).
76. Beijnen, A. J. M. V., Nolte, R. J. M., Drenth, W. & Hezemans, A. M. F. Screw sence of polyisocyanides. Tetrahedron 32, 2017-2019 (1976).
77. Suzuki, Y., Tabei, J., Shiotsuki, M., Inai, Y., Sanda, F. & Masuda, T. Synthesis and helical structure of poly(N-butynylamide)s having various side chains, where the helix is highly affected by the methyl branch and the lactone moiety. Macromolecules 41, 1086-1093 (2008).
78. Kaneko, T., Umeda, Y., Yamamoto, T., Teraguchi, M. & Aoki, T. Assignment of helical sense for poly(phenylacetylene) bearing achiral galvinoxyl chromophore synthesized by helix-sense-selective polymerization. Macromolecules 38, 9420-9426 (2005).
79. Tang, H.-Z., Novak, B. M., He, J. & Polavarapu, P. L. A thermal and solvocontrollable cylindrical nanoshutter based on a single screw-sense helical polyguanidine. Angew. Chem., Int. Ed. 44, 7298-7301 (2005). (Pubitemid 41641754)
80. Kawauchi, T., Kumaki, J., Kitaura, A., Okoshi, K., Kusanagi, H., Kobayashi, K., Sugai, T, Shinohara, H & Yashlma, E Encapsulation of fullerenes in a helical PMMA cavity leading to a robust processable complex with a macromolecular helicity memory. Angew. Chem., Int. Ed. 47, 515-519 (2008).
81. Maaloum, M. A Close encounter with DNA. Eur. Biophys. J. 32, 585-587 (2003).
82. Tanaka, H. & Kawai, T. Partial sequencing of a single DNA molecule with a scanning tunnelling microscope. Nature Nanotech. 4, 518-522 (2009).
83. Sakurai, S.-i., Okoshi, K., Kumaki, J. & Yashima, E. Two-dimensional hierarchical selfassembly of one-handed helical polymers on graphite. Angew. Chem., Int. Ed. 45, 1245-1248 (2006).
84. Sakurai, S.-i., Okoshi, K., Kumaki, J. & Yashima, E. Two-dimensional surface chirality control by solvent-induced helicity inversion of a helical polyacetylene on graphite. J. Am. Chem. Soc. 128, 5650-5651 (2006).
85. Sakurai, S.-i., Ohsawa, S., Nagai, K., Okoshi, K., Kumaki, J. & Yashima, E. Twodimensional helix-bundle formation of a dynamic helical poly(phenylacetylene) with achiral pendant groups on graphite. Angew. Chem., Int. Ed. 46, 7605-7608 (2007).
86. Nolte, R. J. M. Helical poly(lsocyanides). Chem. Soc. Rev. 23, 11-19 (1994).
87. Amabilino, D. B., Serrano, J.-L., Sierra, T. & Veciana, J. Long-range effects of chlrality in aromatic poly(isocyanide)s. J. Polym. Sci., Part A: Polym. Chem. 44, 3161-3174 (2006).
88. Kajitani, T., Okoshi, K., Sakurai, S.-i., Kumaki, J. & Yashima, E. Helix-sense controlled polymerization of a single phenyl isocyanide enantiomer leading to diastereomeric helical polyisocyanides with opposite helix-sense and cholesteric liquid crystals with opposite twist-sense. J. Am. Chem. Soc. 128, 708-709 (2006).
89. Onouchi, H., Okoshi, K., Kajitani, T., Sakurai, S.-i., Nagai, K., Kumaki, J., Onitsuka, K & Yashima, E Two- and three-dimensional smectic ordering of single-handed helical polymers. J. Am. Chem. Soc. 130, 229-236 (2008).
90. Wu, Z.-Q., Nagai, K., Banno, M., Okoshi, K., Onitsuka, K. & Yashima, E. Enantlomerselective and helix-sense-selective living block copolymerization of isocyanide enantiomers initiated by single-handed helical poly(phenyl isocyanide)s. J. Am. Chem. Soc. 131, 6708-6718(2009).
91. Maeda, T., Furusho, Y., Sakurai, S.-I., Kumaki, J., Okoshi, K. & Yashima, E. Doublestranded helical polymers consisting of complementary homopolymers. J. Am. Chem. Soc. 130, 7938-7945 (2008).
92. Schomaker, E. & Challa, G. Complexation of stereoregular poly(methyl methacrylates). 14. the basic structure of the stereocomplex of isotactic and syndiotactic poly(methyl methacrylate). Macromolecules 22, 3337-3341 (1989).
93. Kumaki, J., Kawauchi, T., Okoshi, K., Kusanagi, H. & Yashima, E. Supramolecular helical structure of the stereocomplex composed of complementary isotactic and syndiotactic poly(methyl methacrylate)s as revealed by atomic force microscopy. Angew. Chem., Int. Ed. 46, 5348-5351 (2007). (Pubitemid 47067631)
94. Kusanagi, H., Tadokoro, H. & Chatani, Y. Double strand helix of isotactic poly(methyl methacrylate). Macromolecules 9, 531-532 (1976).
95. Kumaki, J., Kawauchi, T. & Yashima, E. Two-dimensional folded chain crystals of a synthetic polymer in a langmuir-blodgett film. J. Am. Chem. Soc. 127, 5788-5789 (2005). (Pubitemid 40577627)
96. Kusuyama, H., Takase, M., Higashihata, Y., Tseng, H.-T., Chatani, Y. & Tadokoro, H. Structural change of st-PMMA on drawing, absorption and desorption of solvents. Polymer 23, 1256-1258(1982).
97. Kusuyama, H., Miyamoto, N., Chatani, Y. & Tadokoro, H. Crystalline complexes of syndiotactic poly(methyl methacrylate) with some organic solvents. Polym. Commun. 24, 119-122(1983). (Pubitemid 14468237)
98. Kawauchi, T., Kitaura, A., Kumaki, J., Kusanagi, H. & Yashima, E. Helix-sense-controlled synthesis of optically active poly(methyl methacrylate) stereocomplexes. J. Am. Chem. Soc. 130, 11889-11891 (2008).