Photocontrolled self-assembly of a bis-azobenzene-containing α-amino acid

Chemistry - A European Journal

Volumn 19, Issue 47, 2013, Pages 15841-15846

  Mba, Miriam ^a   Mazzier, Daniela ^a   Silvestrini, Simone ^a   Toniolo, Claudio ^a,b   Fatás, Paola ^c   Jiménez, Ana I ^c   Cativiela, Carlos ^c   Moretto, Alessandro ^a,b  

^a UNIVERSITY OF PADOVA   (Italy)

^b CNR   (Italy)

^c CSIC UZA Instituto de Sintesis Quimica y Catalisis Homogenea ISQCH   (Spain)

Author keywords

amino acid; azobenzene; microstructure transition; photoswitch; self assembly

Indexed keywords

AZOBENZENE; SELF ASSEMBLY;

DERIVATIZED AMINO ACIDS; FUNCTIONALIZED GOLD NANOPARTICLES; LIGHT IRRADIATIONS; MORPHOLOGICAL TRANSITIONS; PHOTO-RESPONSIVE; PHOTOSWITCH; SUPRAMOLECULAR STRUCTURE; VESICULAR STRUCTURE;

AMINO ACIDS;

AMINO ACID; AZO COMPOUND; AZOBENZENE; GOLD; METAL NANOPARTICLE; PEPTIDE;

ARTICLE; CHEMISTRY; ISOMERISM; METABOLISM; MICROSTRUCTURE TRANSITION; PHOTOSWITCH; SELF-ASSEMBLY; ULTRAVIOLET RADIATION;

AMINO ACID; AZOBENZENE; MICROSTRUCTURE TRANSITION; PHOTOSWITCH; SELF-ASSEMBLY;

AMINO ACIDS; AZO COMPOUNDS; GOLD; ISOMERISM; METAL NANOPARTICLES; PEPTIDES; ULTRAVIOLET RAYS;

EID: 84896546677     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201303015     Document Type: Article

References (51)

1. G. Fuks, R. M. Talom, F. Gauffre, Chem. Soc. Rev. 2011, 40, 2475-2493
2. S. F. M. vanDongen, H.-P. M. DeHoog, R. J. R. W. Peters, M. Nallani, R. J. M. Nolte, J. C. M. vanHest, Chem. Rev. 2009, 109, 6212-6274
3. E. Soussan, S. Cassel, M. Blanzat, I. Rico-Lattes, Angew. Chem. 2009, 121, 280-295
4. Angew. Chem. Int. Ed. 2009, 48, 274-288.
5. Z. Luo, S. Zhang, Chem. Soc. Rev. 2012, 41, 4736-4754
6. C. Valéry, F. Artzner, M. Paternostre, Soft Matter 2011, 7, 9583-9594
7. X. Yan, P. Zhua, J. Li, Chem. Soc. Rev. 2010, 39, 1877-1890
8. I. W. Hamley, Angew. Chem. 2007, 119, 8274-8295
9. Angew. Chem. Int. Ed. 2007, 46, 8128-8147.
10. B. Tian, X. Tao, T. Ren, Y. Weng, X. Lin, Y. Zhang, X. Tang, J. Mater. Chem. 2012, 22, 17404-17414
11. C. Cai, L. Wang, J. Lin, Chem. Commun. 2011, 47, 11189-11203
12. A. Carlsen, S. Lecommandoux, Curr. Opin. Colloid Interface Sci. 2009, 14, 329-339.
13. N. Gour, D. Kedracki, I. Safir, K. X. Ngo, C. Vebert-Nardin, Chem. Commun. 2012, 48, 5440-5442
14. H. Wang, C. Yang, L. Wang, D. Kong, Y. Zhang, Z. Yang, Chem. Commun. 2011, 47, 4439-4441
15. F. Versluis, I. Tomatsu, S. Kehr, C. Fregonese, A. W. J. W. Tepper, M. C. A. Stuart, B. J. Ravoo, R. I. Koning, A. Kros, J. Am. Chem. Soc. 2009, 131, 13186-13187
16. Y. Zhou, M. Kogiso, T. Shimizu, J. Am. Chem. Soc. 2009, 131, 2456-2457
17. S. Ghosh, M. Reches, E. Gazit, S. Verma, Angew. Chem. 2007, 119, 2048-2050
18. Angew. Chem. Int. Ed. 2007, 46, 2002-2004
19. K. Matsuura, K. Murasato, N. Kimizuka, J. Am. Chem. Soc. 2005, 127, 10148-10149.
20. P. Koley, A. Pramanik, Soft Matter 2012, 8, 5364-5374
21. J. Naskar, S. Roy, A. Joardar, S. Das, A. Banerjee, Org. Biomol. Chem. 2011, 9, 6610-6615
22. S. Maity, P. Jana, S. K. Maity, D. Haldar, Langmuir 2011, 27, 3835-3841
23. A. Mishra, J. J. Panda, A. Basu, V. S. Chauhan, Langmuir 2008, 24, 4571-4576
24. S. Ghosh, S. K. Singh, S. Verma, Chem. Commun. 2007, 2296-2298
25. S. Vauthey, S. Santoso, H. Gong, N. Watson, S. Zhang, Proc. Natl. Acad. Sci. USA 2002, 99, 5355-5360.
26. R. Orbach, L. Adler-Abramovich, S. Zigerson, I. Mironi-Harpaz, D. Seliktar, E. Gazit, Biomacromolecules 2009, 10, 2646-2651
27. X. Yan, Y. Cui, Q. He, K. Wang, J. Li, W. Mu, B. Wang, Z. Ouyang, Chem. Eur. J. 2008, 14, 5974-5980
28. X. Yan, Q. He, K. Wang, L. Duan, Y. Cui, J. Li, Angew. Chem. 2007, 119, 2483-2486
29. Angew. Chem. Int. Ed. 2007, 46, 2431-2434
30. M. Reches, E. Gazit, Nano Lett. 2004, 4, 581-585.
31. P. Fatás, E. Longo, F. Rastrelli, M. Crisma, C. Toniolo, A. I. Jiménez, C. Cativiela, A. Moretto, Chem. Eur. J. 2011, 17, 12606-12611.
32. A. Mahler, M. Reches, M. Rechter, S. Cohen, E. Gazit, Adv. Mater. 2006, 18, 1365-1370
33. V. Jayawarna, M. Ali, T. A. Jowitt, A. F. Miller, A. Saiani, J. E. Gough, R. V. Ulijn, Adv. Mater. 2006, 18, 611-614.
34. M. Reches, E. Gazit, Science 2003, 300, 625-627.
35. Incorporation of Fmoc at the N-terminus of dipeptides often results in the formation of nanofibers (hydrogels):, Y. Zhang, H. Gu, Z. Yang, B. Xu, J. Am. Chem. Soc. 2003, 125, 13680-13681.
36. S. Sutton, N. L. Campbell, A. I. Cooper, M. Kirkland, W. J. Frith, D. J. Adams, Langmuir 2009, 25, 10285-10291
37. Z. Yang, H. Gu, D. Fu, P. Gao, J. K. Lam, B. Xu, Adv. Mater. 2004, 16, 1440-1444.
38. C.-D. Chang, M. Waki, M. Ahmad, J. Meienhofer, E. O. Lundell, J. D. Haug, Int. J. Pept. Protein Res. 2009, 15, 59-66
39. H. Cao, X. Zhu, M. Liu, Angew. Chem. 2013, 125, 4216-4220
40. Angew. Chem. Int. Ed. 2013, 52, 4122-4126.
41. I. M. Rio-Echevarria, R. Tavano, V. Causin, E. Papini, F. Mancin, A. Moretto, J. Am. Chem. Soc. 2011, 133, 8-11.
42. D. W. P. M. Löwik, E. H. P. Leunissen, M. vandenHeuvel, M. B. Hansen, J. C. M. vanHest, Chem. Soc. Rev. 2010, 39, 3394-3412
43. R. J. Mart, R. D. Osborne, M. M. Stevens, R. V. Ulijn, Soft Matter 2006, 2, 822-835.
44. Y. Zhao, Macromolecules 2012, 45, 3647-3657
45. J. Du, R. K. O'Reilly, Soft Matter 2009, 5, 3544-3561
46. M.-H. Li, P. Keller, Soft Matter 2009, 5, 927-937
47. F. Meng, Z. Zhong, J. Feijen, Biomacromolecules 2009, 10, 197-209.
48. G. Liu, C.-M. Dong, Biomacromolecules 2012, 13, 1573-1583
49. S. Kumar, J.-F. Allard, D. Morris, Y. L. Dory, M. Lepage, Y. Zhao, J. Mater. Chem. 2012, 22, 7252-7257
50. V. K. Kotharangannagari, A. Sanchez-Ferrer, J. Ruokolainen, R. Mezzenga, Macromolecules 2011, 44, 4569-4573.
51. S. Lee, S. Oh, J. Lee, Y. Malpani, Y.-S. Jung, B. Kang, J. Y. Lee, K. Ozasa, T. Isoshima, S. Y. Lee, M. Hara, D. Hashizume, J.-M. Kim, Langmuir 2013, 29, 5869-5877.