Helical polyisocyanides with fan-shaped pendants

Macromolecules

Volumn 42, Issue 2, 2009, Pages 560-567

  Kajitani, Takashi ^a,c   Lin, Hongzhen ^b   Nagai, Kanji ^a,b   Okoshi, Kento ^a   Onouchi, Hisanari ^a   Yashima, Eiji ^a,b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

^c RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CIRCULAR DICHROISM SPECTROSCOPY; DICHROISM; LIQUID CRYSTAL POLYMERS; PALLADIUM; PALLADIUM COMPOUNDS; PLATINUM; PLATINUM COMPOUNDS; POLYMERS;

ALKOXY CHAINS; CIRCULAR DICHROISMS; COTTON EFFECTS; HELICAL SENSE; HELICAL STRUCTURES; MICROSCOPIC OBSERVATIONS; OPTICALLY ACTIVES; PALLADIUM PLATINUMS; POLYISOCYANIDES; STEREOGENIC CENTERS; STERIC EFFECTS; X-RAY DIFFRACTION MEASUREMENTS;

LIVING POLYMERIZATION;

EID: 61549132856     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma802345g     Document Type: Article

References (63)

1. For reviews on helical polymers, see: (a) Okamoto, Y.; Nakano, T. Chem. Rev. 1994, 94, 349-372.
2. (b) Nolte, R. J. M. Chem. Soc. Rev. 1994, 23, 11-19.
3. (c) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, V. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154.
4. (d) Nakano, T.; Okamoto, Y. Chem. Rev. 2001, 101, 4013-4038.
5. (e) Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M.; Sommerdijk, N. A. J. M. Chem. Rev. 2001, 101, 4039-4070.
6. (f) Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A: Chem. 2002, 190, 197-205.
7. (g) Fujiki, M.; Koe, J. R.; Terao, K.; Sato, T.; Teramoto, A.; Watanabe, J. Polym. J. 2003, 35, 297-344.
8. (h) Yashima, E.; Maeda, K.; Nishimura, T. Chem.-Eur. J. 2004, 10, 43-51.
9. (i) Suginome, M.; Ito, Y. Adv. Polym. Sci. 2004, 17, 77-136.
10. (j) Lam, J. W. Y.; Tang, B. Z. Acc. Chem. Res. 2005, 38, 745-754.
11. (k) Aoki, T.; Kaneko, T.; Teraguchi, M. Polymer 2006, 37, 717-735.
12. (l) Maeda, K.; Yashima, E. Top. Curr. Chem. 2006, 265, 47-88.
13. (m) Yashima, E.; Maeda, K. Macromolecules 2008, 41, 3-12.
14. (n) Pijper, D.; Feringa, B. L. Soft Matter 2008, 4, 1349-1372.
15. (o) Yashima, E.; Maeda, K.; Furusho, Y. Acc. Chem. Res. 2008, 41, 1166-1180.
16. For selective references of helix-sense-selective polymerization of achiral monomers with chiral initiators or catalysts, see: (a) Okamoto, Y.; Suzuki, K.; Ohta, K.; Hatada, K.; Yuki, H. J. Am. Chem. Soc. 1979, 101, 4763-4765.
17. (b) Kamer, P. C. J.; Cleiji, M. C.; Nolte, R. J. M.; Harada, T.; Hezemans, A. M. F.; Drenth, W. J. Am. Chem. Soc. 1988, 110, 1581-1587.
18. (c) Nakano, T.; Okamoto, Y.; Hatada, K. J. Am. Chem. Soc. 1992, 114, 1318-1329.
19. (d) Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926-7927.
20. (e) Vogl, O.; Jaycox, G. D.; Kratky, C.; Simonsick, W. J.; Hatada, K. Ace. Chem. Res. 1992, 25, 408-413.
21. (f) Okamoto, Y.; Matsuda, M.; Nakano, T.; Yashima, E. Polym. J. 1993, 25, 391-396.
22. (g) Aoki, T.; Kaneko, T.; Maruyama, N.; Sumi, A.; Takahashi, M.; Sato, T.; Teraguchi, M. J. Am. Chem. Soc. 2003, 125, 6346-6347.
23. (h) Tian, G.; Lu, Y.; Novak, B. M. J. Am. Chem. Soc. 2004, 126, 4082-4083.
24. For leading references of hydrogen-bond-assisted helical polymers, see ref 2g and: (a) Cornelissen, J. J. L. M.; Fischer, M.; Sommerdijk, N. A. J. M.; Nolte, R. J. M Science 1998, 280, 1427-1430.
25. (b) Cornelissen, J. J. L. M.; Donners, J. J. J. M.; de Gelder, R.; Graswinckel, W. S.; Metselaar, G. A.; Rowan, A. E.; Sommerdijk, N. A. J. M.; Nolte, R. J. M. Science 2001, 293, 676-680.
26. (c) Nomura, R.; Tabei, J.; Masuda, T. J. Am. Chem. Soc. 2001, 123, 8430-8431.
27. (d) Cornelissen, J. J. L. M.; Graswinckel, W. S.; Rowan, A. E.; Sommerdijk, N. A. J. M.; Nolte, R. J. M. /. Polym. Sci., Part A: Polym. Chem. 2003, 41, 1725-1736.
28. (e) Li, B. S.; Cheuk, K. K. L.; Ling, L.; Chen, J.; Xiao, X.; Bai, C.; Tang, B. Z. Macromolecules 2003, 36, 77-85.
29. (f) Metselaar, G. A.; Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M. Angew. Chem., Int. Ed. 2005, 44, 1990-1993.
30. (g) Okoshi, K.; Sakajiri, K.; Kumaki, J.; Yashima, E. Macromolecules 2005, 38, 4061-4064.
31. (h) Okoshi, K.; Sakurai, S.-i.; Ohsawa, S.; Kumaki, J.; Yashima, E. Angew. Chem., Int. Ed. 2006, 45, 8173-8176.
32. (a) Ramos, E.; Bosch, J.; Serrano, J.-L.; Sierra, T.; Veciana, J. J. Am. Chem. Soc. 1996, 118, 4703-4704.
33. (b) Amabilino, D. B.; Ramos, E.; Serrano, J.-L.; Sierra, T.; Veciana, J. J. Am. Chem. Soc. 1998, 120, 9126-9134.
34. (c) Amabilino, D. B.; Ramos, E.; Serrano, J.-L.; Veciana, J. Adv. Mater. 1998, 10, 1001-1005.
35. (d) Gomar-Nadal, E.; Veciana, J.; Rovira, C.; Amabilino, D. B. Adv. Mater. 2005, 17, 2095-2098.
36. 1e,3a,b,b.d.f .
37. See (f) Hasegawa, T.; Kondoh, S.; Matsuura, K.; Kobayashi, K. Macromolecules 1999, 32, 6595-6603.
38. (g) Yamada, Y.; Kawai, T.; Abe, J.; Iyoda, T. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 399-408.
39. (a) Oda, M.; Nothofer, H.-G.; Scherf, U.; Sunjic, V.; Richter, D.; Regenstein, W.; Neher, D. Macromolecules 2002, 35, 6792-6798.
40. (b) Yamazaki, K.; Yokoyama, A.; Yokozawa, T. Macromolecules 2002, 35, 2432-2434.
41. (c) Henze, O.; Feast, W. J.; Gardebien, F.; Jonkheijm, P.; Lazzaroni, R.; Leclere, P.; Meijer, E. W.; Schenning, A. P. H. J. J. Am. Chem. Soc. 2006, 128, 5923-5929.
42. (d) Zhi, J.; Zhu, Z.; Liu, A.; Cui, J.; Wan, X.; Zhou, Q. Macromolecules 2008, 41, 1594-1597.
43. Schenning, A. P. H. J.; Fransen, M.; Meijer, E. W. Macromol. Rapid Commun. 2002, 23, 265-270.
44. (a) Percec, V.; Rudick, J. G.; Peterca, M.; Wagner, M.; Obata, M.; Mitchell, C. M.; Cho, W.-D.; Balagurusamy, V. S. K.; Heiney, P. A. J. Am. Chem. Soc. 2005, 127, 15257-15264.
45. (b) Percec, V.; Aqad, E.; Peterca, M.; Rudick, J. G.; Lemon, L.; Ronda, J. C.; De, B. B.; Heiney, P. A.; Meijer, E. W. J. Am. Chem. Soc. 2006, 128, 16365-16372.
46. (c) Rudick, J. G.; Percec, V. New J. Chem. 2007, 31, 1083-1096.
47. Kajitani, T.; Okoshi, K.; Sakurai, S.-i.; Kumaki, J.; Yashima, E. J. Am. Chem. Soc. 2006, 128, 708-709.
48. Kajitani, T.; Okoshi, K.; Yashima, E. Macromolecules 2008, 41, 1601-1611.
49. (a) Onitsuka, K.; Joh, T.; Takahashi, S. Bull. Chem. Soc. Jpn. 1992, 65, 1179-1181.
50. (b) Onitsuka, K.; Joh, T.; Takahashi, S. Angew. Chem., Int. Ed. Engl. 1992, 31, 851-852.
51. (c) Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Angew. Chem., Int. Ed. 1996, 35, 1554-1556.
52. (d) Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Chem. -Eur. J. 2000, 6, 983-993.
53. (e) Takei, F.; Hayashi, H.; Onitsuka, K.; Kobayashi, N.; Takahashi, S. Angew. Chem., Int. Ed. 2001, 40, 4092-4094.
54. (f) Hida, N.; Takei, F.; Onitsuka, K.; Shiga, K.; Asaoka, S.; Iyoda, T.; Takahashi, S. Angew. Chem., Int. Ed. 2003, 42, 4349-4352.
55. Recently, polyisocyanides bearing achiral dendronized pendant groups were prepared, and their thermotropic LC properties and the formation of supramolecular nanostructures were reported. See: Tian, Y.; Kamata, K.; Yoshida, H.; Iyoda, T. Chem. -Eur. J. 2006, 12, 584-591.
56. Yelamaggad, C. V.; Achalkumar, A. S. Tetrahedron Lett. 2006, 47, 7071-7075.
57. Onouchi, H.; Okoshi, K.; Kajitani, T.; Sakurai, S.-i.; Nagai, K.; Kumaki, J.; Onitsuka, K.; Yashima, E. J. Am. Chem. Soc. 2008, 130, 229-236.
58. Ishikawa, M.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2002, 124, 7448-7458.
59. Deming, T. J.; Novak, B. M. Macromolecules 1991, 24, 5478-5480.
60. Sun, H. J. Phys. Chem. B 1998, 102, 7338-7364.
61. first value display a right-handed helical structure. See refs 8 and 13.
62. Onitsuka, K.; Mori, T.; Yamamoto, M.; Takei, F.; Takahashi, S. Macromolecules 2006, 39, 7224-7231.
63. Percec, V.; Ann, C. H.; Ungar, G.; Yeardley, D. J. P.; Moller, M.; Sheiko, S. S. Nature 1998, 391, 161-164.