Stimuli-responsive azulene-based conjugated oligomers with polyaniline-like properties

Journal of the American Chemical Society

Volumn 133, Issue 26, 2011, Pages 10046-10049

  Amir, Elizabeth ^a   Amir, Roey J ^a   Campos, Luis M ^b   Hawker, Craig J ^a  

^a University of California   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZULENES; BUILDING BLOCKES; CONJUGATED MATERIALS; CONJUGATED OLIGOMER; FLUORESCENCE SWITCHING; MODE OF INCORPORATION; OPTICAL BANDS; SEVEN-MEMBERED RINGS; STIMULI-RESPONSIVE; STIMULI-RESPONSIVE MATERIALS;

OLIGOMERS; THIOPHENE;

POLYANILINE;

ACID; AZULENE; OLIGOMER; POLYANILINE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; FLUORESCENCE; PHYSICAL CHEMISTRY;

EID: 79959900707     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja203267g     Document Type: Article

References (28)

1. St. Pfau, A.; Plattner, P. A. Helv. Chim. Acta 1939, 22, 202
2. Carret, S.; Blanc, A.; Coquerel, Y.; Berthod, M.; Greene, A. E.; Depreés, J.-P. Angew. Chem., Int. Ed. 2005, 44, 5130
3. Crombie, A. L.; Kane, J. L., Jr.; Shea, K. M.; Danheiser, R. L. J. Org. Chem. 2004, 69, 8652
4. Grellmann, K. H.; Heilbronner, E.; Seiler, P.; Weller, A. J. Am. Chem. Soc. 1968, 90, 4238
5. Wang, X.; Ng, J. K.-P.; Jia, P.; Lin, T.; Cho, C. M.; Xu, J.; Lu, X.; He, C. Macromolecules 2009, 42, 5534
6. Wang, F.; Lai, Y.-H.; Han, M.-Y. Macromolecules 2004, 37, 3222
7. Wang, F.; Lai, Y.-H. Macromolecules 2003, 36, 536
8. Schmitt, S.; Baumgarten, M.; Simon, J.; Hafner, K. Angew. Chem., Int. Ed. 1998, 37, 1077
9. Ito, S.; Morita, N. Eur. J. Org. Chem. 2009, 4567
10. Reiter, S. E.; Dunn, L. C.; Houk, K. N. J. Am. Chem. Soc. 1977, 99, 4199
11. Lou, Y.; Chang, J.; Jorgensen, J.; Lemal, D. M. J. Am. Chem. Soc. 2002, 124, 15302
12. Rozen, S.; Bareket, Y. J. Org. Chem. 1997, 62, 1457
13. Rozen, S.; Bareket, Y. J. Chem. Soc., Chem. Commun. 1994, 1959
14. Amir, E.; Rozen, S. Angew. Chem., Int. Ed. 2005, 44, 7374
15. Moiseev, A. M.; Balenkova, E. S.; Nenajdenko, V. G. Russ. Chem. Bull., Int. Ed. 2006, 55, 141
16. Mukherjee, D.; Dunn, L. C.; Houk, K. N. J. Am. Chem. Soc. 1979, 101, 251
17. Frisch, M. J.; Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
18. Bjornholm, T.; Greve, D. R.; Reitzel, N.; Hassenkam, T.; Kjaer, K.; Howes, P. B.; Larsen, N. B.; Bogelund, J.; Jayaraman, M.; Ewbank, P. C.; McCullough, R. D. J. Am. Chem. Soc. 1998, 120, 7643
19. Rossi, R.; Carpita, A.; Ciofalo, M.; Lippolis, V. Tetrahedron 1991, 47, 8443
20. Carsten, B.; He, F.; Son, H. J.; Xu, T.; Yu, L. Chem. Rev. 2011, 111, 1493
21. Tierney, S.; Heeney, M.; McCulloch, I. Synth. Met. 2005, 148, 195
22. Plattner, P. A.; Heilbronner, E.; Weber, S. Helv. Chim. Acta 1952, 35, 1036
23. Oda, M.; Fukuta, A.; Kajioka, T.; Uchiyama, T.; Kainuma, H.; Miyatake, R.; Kuroda, S. Tetrahedron 2000, 56, 9917
24. Wang, F.; Lai, Y.-H.; Kocherginsky, N. M.; Kosteski, Y. Y. Org. Lett. 2003, 5, 995
25. Beer, M.; Longuet-Higgins, H. C. J. Chem. Phys. 1955, 23, 1390
26. Rentzepis, P. M. Chem. Phys. Lett. 1969, 3, 717
27. Hawker, C. J.; Saville, P. M.; White, J. W. J. Org. Chem. 1994, 59, 3503
28. Varotto, A.; Treat, N. D.; Jo, J.; Shuttle, C. G.; Batara, N. A.; Brunetti, F. G.; Seo, J. H.; Chabinyc, M. L.; Hawker, C. J.; Heeger, A. J.; Wudl, F. Angew. Chem., Int. Ed. 2011, 50, 5166