Synthesis of chiral polyacetylenes carrying amino acids and azobenzenes and transformation of the higher order structure by photoirradiation

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 42, Issue 18, 2004, Pages 4641-4647

  Sanda, Fumio ^a   Teraura, Takayuki ^a   Masuda, Toshio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Amino acids; Azo polymers; Irradiation; N propargylamide; Polyacetylenes; Stimuli sensitive polymers

Indexed keywords

AMINO ACIDS; BENZENE; CATALYSIS; CONFORMATIONS; ELECTRIC CONDUCTIVITY; ENERGY TRANSFER; HYDROGEN BONDS; ISOMERIZATION; PARAMAGNETISM; PROTEINS; STRUCTURE (COMPOSITION); ULTRAVIOLET RADIATION;

AZO POLYMERS; N-PROPARGYLAMIDE; STIMULI-SENSITIVE POLYMERS; UV IRRADIATION;

POLYACETYLENES;

EID: 4544363943     PISSN: 0887624X     EISSN: None     Source Type: Journal    
DOI: 10.1002/pola.20374     Document Type: Article

References (46)

1. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987.
2. Amino Acids, Peptides, Porphyrins, and Alkaloids; Kelly, J. W., Ed.; Elsevier: Oxford, 1999.
3. Sanda, F.; Endo, T. Macromol Chem Phys 1999, 200, 2651-2661.
4. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem Rev 2001, 101, 3893-4012.
5. Shirakawa, H.; Masuda, T.; Takeda, K. The Chemistry of Triple-Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, England, 1994; pp 945-1016.
6. Masuda, T. In Polymeric Material Encyclopedia; Salamone, J. C., Ed.; CRC: New York, 1996; Vol. 1, pp 32-39.
7. Gao, G.; Sanda, F.; Masuda, T. Macromolecules 2003, 36, 3932-3937.
8. Li, B. S.; Cheuk, K. K. L.; Yang, D.; Lam, J. W. Y.; Wan, L. J.; Bai, C.; Tang, B. Z. Macromolecules 2003, 36, 5447-5450.
9. Cheuk, K. K. L.; Lam, J. W. Y.; Chen, J.; Lai, L. M.; Tang, B. Z. Macromolecules 2003, 36, 5947-5959.
10. Griffiths, J. Chem Soc Rev 1972, 1, 481-493.
11. Macromolecular Symposia (Azobenzene-Containing Materials); Natansohn, A., Ed.; Wiley-VCH: Weinheim, 1999; Vol. 139.
12. Azobenzene-Containing Polymers: Digital and Holographic Storage; Natansohn, A.; Rochon, P., Eds.; ACS Symposium Series 672; American Chemical Society: Washington, DC, 1997; pp 236-250.
13. Xie, S.; Natansohn, A.; Rochon, P. Chem Mater 1993, 5, 403-411.
14. Ho, C.-H.; Yang, K.-N.; Lee, S.-N. J Polym Sci Part A: Polym Chem 2001, 39, 2296-2307.
15. Buffeteau, T.; Labarthet, F. L.; Pézolet, M.; Sourisseau, C. Macromolecules 2001, 34, 7514-7521.
16. Yamamoto, T.; Ohashi, A.; Yoneyama, S.; Hasegawa, M.; Tsutsumi, O.; Kanazawa, A.; Shiono, T.; Ikeda, T. J Phys Chem B 2001, 105, 2308-2313.
17. Iftime, G.; Lagugné, F.; Labarthet, F. L.; Natansohn, A.; Rochon, P. J Am Chem Soc 2000, 122, 12646-12650.
18. Andruzzi, L.; Altomare, A.; Ciardelli, F.; Solaro, R. Macromolecules 1999, 32, 448-454.
19. Barrett, C. J.; Natansohn, A. L.; Rochon, P. L. J Phys Chem 1996, 100, 8836-8842.
20. Ikeda, T.; Tsutsumi, O. Science 1995, 268, 1873-1875.
21. Seki, T.; Fukuda, K.; Ichimura, K. Langmuir 1999, 15, 5098-5101.
22. Kago, K.; Fürst, M.; Matsuoka, H.; Yamaoka, H.; Seki, T. Langmuir 1999, 15, 2237-2240.
23. Clavier, G.; Ilhan, F.; Rotello, V. M. Macromolecules 2000, 33, 9173-9175.
24. Altomare, A.; Ciardelli, F.; Tirelli, N.; Solaro, R. Macromolecules 1997, 30, 1298-1303.
25. Zagórska, M.; Kulszewicz-Bajer, I.; Proñ, A.; Sukiennik, J.; Raimond, P.; Kajzar, F.; Attias, A.-J.; Lapkowski, M. Macromolecules 1998, 31, 9146-9153.
26. Lévesque, I.; Leclerc, M. Macromolecules 1997, 30, 4347-4352.
27. Rasmussen, P. H.; Ramanujam, P. S.; Hvilsted, S.; Berg, R. H. J Am Chem Soc 1999, 121, 4738-4743.
28. Alonso, M.; Reboto, V.; Guiscardo, L.; Mate, V.; Rodriguez-Cabello, J. C. Macromolecules 2001, 34, 8072-8077.
29. Mruk, R.; Zentel, R. Macromolecules 2002, 35, 185-192.
30. Mayer, S.; Zentel, R. Macromol Rapid Commun 2000, 21, 927-930.
31. Mayer, S.; Maxein, G.; Zentel, R. Macromolecules 1998, 31, 8522-8525.
32. Mayer, S.; Zentel, R. Macromol Chem Phys 1998, 199, 1675-1682.
33. Müller, M.; Zentel, R. Macromolecules 1996, 29, 1609-1617.
34. Müller, M.; Zentel, R. Macromolecules 1994, 27, 4404-4406.
35. Müller, M.; Zentel, R. Makromol Chem 1993, 194, 101-116.
36. Steinern, C.; Janshoff, A.; Vollmer, M. S.; Ghadiri, M. R. Langmuir 1999, 15, 3956-3964.
37. Vollmer, M. S.; Clark, T. D.; Steinern, C.; Ghadiri, M. R. Angew Chem Int Ed Engl 1999, 38, 1598-1601.
38. Balzani, V.; Credi, A.; Venturi, M. Coord Chem Rev 1998, 171, 3-16.
39. Schrock, R. R.; Osborn, J. A. Inorg Chem 1970, 2339-2343.
40. Kishimoto, Y.; Itou, M.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromolecules 1995, 28, 6662-6666.
41. Green, M. M.; Park, J. W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew Chem Int Ed Engl 1999, 38, 3138-3154.
42. Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860-1866.
43. Gao, G.; Sanda, F.; Masuda, T. Macromolecules 2003, 36, 3938-3943.
44. Upon UV-light irradiation of the azobenzene-containing monomer (Azo), the absorption at 320 nm of trans-azobenzene gradually decreased and disappeared after 20 min. In agreement with this, the absorption at 440 nm of cis-azobenzene appeared and increased. Upon further irradiation with visible light for 20 min, the absorption at 320 nm almost recovered, and that at 440 nm disappeared; It was concluded that the azobenzene moiety of the monomer reversibly isomerized between trans and cis forms. It was therefore reasonable to conclude that the azobenzene moiety of the polymer side chain also underwent reversible photoisomerization.
45. Nomura, R.; Tabei, J.; Masuda, T. Macromolecules 2002, 35, 2955-2961.
46. Nomura, R.; Tabei, J.; Nishiura, S.; Masuda, T. Macromolecules 2003, 36, 561-564.