Synthesis, chiroptical properties, and photoresponsiveness of optically active poly(m -phenyleneethynylene)s containing azobenzene moieties

Macromolecules

Volumn 44, Issue 9, 2011, Pages 3338-3345

  Sogawa, Hiromitsu ^a   Shiotsuki, Masashi ^a   Matsuoka, Hideki ^a   Sanda, Fumio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATED STRUCTURE; AZOBENZENE MOIETY; CHIROPTICAL PROPERTIES; HELICAL CONFORMATION; HIGHER-ORDER STRUCTURE; METHOXY; N ,N-DIMETHYLFORMAMIDE; OPTICALLY ACTIVE; PHENYLENEETHYNYLENE; PHENYLGLYCINES; PHOTORESPONSIVENESS; SPECTROSCOPIC DATA; THERMALLY STABLE; UV- AND; VISIBLE-LIGHT IRRADIATION;

DIMETHYLFORMAMIDE;

POLYMERS;

EID: 79955646294     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma200281e     Document Type: Article

References (60)

1. Reviews: Yashima, E.; Maeda, K.; Iida, H.; Furusho, Y.; Nagai, K. Chem. Rev. 2009, 109, 6102-6211
2. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011
3. Nakano, T.; Okamoto, Y. Chem. Rev. 2001, 101, 4013-4038
4. Reviews: David, B. A.; Serrano, J.; Sierra, T.; Veciana, J. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 3161-3174
5. Suginome, M.; Ito, Y. Adv. Polym. Sci. 2004, 171, 77-136
6. Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M.; Sommerdijk, N. A. J. M. Chem. Rev. 2001, 101, 4039-4070
7. Reviews: Shiotsuki, M.; Sanda, F.; Masuda, T. Polym. Chem., in press. DOI: 10.1039/c0py00333f.
8. Masuda, T. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 165-180
9. Aoki, T.; Kaneko, T.; Teraguchi, M. Polymer 2006, 47, 4867-4892
10. Reviews: Kane-Maguire, L. A. P.; Wallace, G. G. Chem. Soc. Rev. 2010, 39, 2545-2576
11. Hoeben, F. J. M.; Jonkheijim, P.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491-1546
12. Review: Ajayaghosh, A.; Praveen, V. K. Acc. Chem. Res. 2007, 40, 644-656
13. Reviews: Bunz, U. H. F. Macromol. Rapid Commun. 2009, 30, 772-805
14. Smaldone, R. A.; Moore, J. S. Chem.-Eur. J. 2008, 14, 2650-2657
15. Bunz, U. H. F. Adv. Polym. Sci. 2005, 177, 1-52
16. Fukuhara, G.; Inoue, Y. J. Am. Chem. Soc. 2011, 133, 768-770
17. Tamura, K.; Miyabe, T.; Iida, H.; Yashima, E. Polym. Chem. 2011, 2, 91-98
18. Fukuhara, G.; Inoue, Y. Chem.-Eur. J. 2010, 16, 7859-7864
19. Smaldone, R. A.; Moore, J. S. J. Am. Chem. Soc. 2007, 129, 5444-5450
20. Ikeda, M.; Furusho, Y.; Okoshi, K.; Tanahara, S.; Maeda, K.; Nishio, S.; Mori, T.; Yashima, E. Angew. Chem., Int. Ed. 2006, 45, 6491-6495
21. Abe, H.; Masuda, N.; Waki, M.; Inouye, M. J. Am. Chem. Soc. 2005, 127, 16189-16196
22. Yamamoto, T.; Yamada, T.; Nagata, Y.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 7889-7901
23. Terada, K.; Masuda, T.; Sanda, F. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 2596-2602
24. Maeda, K.; Tanaka, K.; Morino, K.; Yashima, E. Macromolecules 2007, 40, 6783-6785
25. Kakuchi, R.; Shimada, R.; Tago, Y.; Sakai, R.; Satoh, T.; Kakuchi, T. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 1683-1689
26. Kakuchi, R.; Kodama, T.; Shimada, R.; Tago, Y.; Sakai, R.; Satoh, T.; Kakuchi, T. Macromolecules 2009, 42, 3892-3897
27. Thomas, S. W, III; Joly, G. D.; Swager, T. M. Chem. Rev. 2007, 107, 1339-1386
28. Li, C.; Guo, Y.; Lv, J.; Xu, J.; Li, Y.; Wang, S.; Liu, H.; Zhu, D. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 1403-1412
29. Zhao, X.; Schanze, K. S. Langmuir 2006, 22, 4856-4862
30. Arnt, L.; Tew, G. N. Macromolecules 2004, 37, 1283-1288
31. Liu, R.; Sogawa, H.; Shiotsuki, M.; Masuda, T.; Sanda, F. Polymer 2010, 51, 2255-2263
32. Liu, R.; Shiotsuki, M.; Masuda, T.; Sanda, F. Macromolecules 2009, 42, 6115-6122
33. Reviews: Seki, T. Bull. Chem. Soc. Jpn. 2007, 80, 2084-2109
34. Natansohn, A.; Ronchon, P. Chem. Rev. 2002, 102, 4139-4175
35. Tamai, N.; Miyasaka, H. Chem. Rev. 2000, 100, 1875-1890
36. Ercole, F.; Davis, T. P.; Evans, R. A. Polym. Chem. 2010, 1, 37-54
37. Stoll, R. S.; Peters, M. V.; Kuhn, A.; Helices, S.; Goddard, R.; Buhl, M.; Thiele, C. M.; Hecht, S. J. Am. Chem. Soc. 2009, 131, 357-367
38. Masiero, S.; Lena, S.; Pieraccini, S.; Spada, G. P. Angew. Chem., Int. Ed. 2008, 47, 3184-3187
39. Yamada, M.; Kondo, M.; Mamiya, J.; Yu, Y.; Kinoshita, M.; Barrett, C. J.; Ikeda, T. Angew. Chem., Int. Ed. 2008, 47, 4986-4988
40. Koumura, N.; Kudo, M.; Tamoki, N. Langmuir 2004, 20, 9897-9990
41. Furusho, Y.; Tanaka, Y.; Maeda, T.; Ikeda, M.; Yashima, E. Chem. Commun. 2007, 3174-3176
42. Fujii, T.; Shiotsuki, M.; Inai, Y.; Sanda, F.; Masuda, T. Macromolecules 2007, 40, 7079-7088
43. Khan, A.; Hecht, S. Chem.-Eur. J. 2006, 12, 4764-4774
44. Zhao, H.; Sanda, F.; Masuda, T. Polymer 2006, 47, 2596-2602
45. Mayer, S.; Zentel, R. Prog. Polym. Sci. 2001, 26, 1973-2013
46. Bérubé, M.; Poirier, D. Org. Lett. 2004, 6, 3127-3130
47. ten Brink, G.; Vis, J. M.; Arends, I. W. C. E.; Sheldon, R. A. Tetrahedron 2002, 58, 3977-3983
48. Anspon, H. D. Org. Synth. 1955, 3, 711-712
49. 3 (50 mM) to confirm the purity of the polymer chain. One broad signal assignable to -C=C- was observed around 80.1 ppm. No peak assignable to -C=C-C=C- was observed around 74 ppm (e.g., Ph-C=C-C=C-Ph 74.2 ppm). Consequently, it is concluded that oxidative acetylene coupling, a typical side reaction of the Sonogashira-Hagihara coupling, does not take place during the polymerization, and the present polymer does not contain diacetylene units. The relatively low molecular weights of the polymers may be caused by a small deviation from equivalency between the diiode monomers and diyne monomers due to the small scale of the polymerization (0.30 mmol).
50. -3 wt %)] attributable to the aggregates. It is presumed that this is due to the difference in sample concentrations between DLS and CD measurements. The concentrations of the DLS samples were 65-80 times higher than those of the CD samples. Because of the different requirements of sample concentrations, we could not obtain the data of DLS and CD at the same concentration.
51. Prince, R. B.; Brunsyeld, L.; Meijer, E. W.; Moore, J. S. Angew. Chem., Int. Ed. 2000, 39, 228-230
52. Prince, R.; Saven, J. G.; Wolynens, P. G.; Moore, J. S. J. Am. Chem. Soc. 1999, 121, 3114-3121
53. Aggregation also seems to contribute to the thermal stability in the case of poly(1b - 2a).
54. Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563
55. Gore, P. R.; Wheeler, O. H. J. Org. Chem. 1961, 26, 3295-3298
56. Moniruzzaman, M.; Talbot, J. D. R.; Sabey, C. J.; Fernando, G. F. J. Appl. Polym. Sci. 2006, 100, 1103-1112
57. Adisa, B.; Bruce, D. A. J. Phys. Chem. B 2005, 109, 7548-7556
58. Adisa, B.; Bruce, D. A. J. Phys. Chem. B 2005, 109, 19952-19959
59. Lee, O. S.; Saven, J. G. J. Phys. Chem. B 2004, 108, 11988-11994
60. Halgren, T. A. J. Comput. Chem. 1996, 17, 490 - 519. The molecular mechanics calculation was carried out with Wavefunction, Inc., Spartan '08 Macintosh.