Chlorophyll-derived thermochromic sensor based on α-amino alcohol adduct formation via reversible intramolecular cyclization

Chemistry Letters

Volumn 38, Issue 8, 2009, Pages 796-797

  Sasaki, Shin Ichi ^a,b   Kotegawa, Yuki ^a   Azuma, Kimiko ^a   Kunieda, Michio ^a   Tamiaki, Hitoshi ^a  

^a RITSUMEIKAN UNIVERSITY   (Japan)

^b NAGAHAMA INSTITUTE OF BIO SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67650674355     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2009.796     Document Type: Article

References (29)

1. a) A. Gryshuk, Y. Chen, L. N. Goswami, S. Pandey, J. R. Missert, T. Ohulchanskyy, W. Potter, P. N. Prasad, A. Oseroff, R. K. Pandey, J. Med. Chem. 2007, 50, 1754.
2. b) W.-T. Li, H.-W. Tsao, Y.-Y. Chen, S.-W. Cheng, Y.-C. Hsu, Photochem. Photobiol. Sci. 2007, 6, 1341.
3. c) S. K. Pandey, M. Sajjad, Y. Chen, X. Zheng, R. Yao, J. R. Missert, C. Batt, H. A. Nabi, A. R. Oseroff, R. K. Pandey, J. Med. Chem. 2009, 52, 445, and references therein.
4. a) X.-F. Wang, Y. Koyama, H. Nagae, Y. Wada, S. Sasaki, H. Tamiaki, J. Phys. Chem. C 2008, 112, 4418.
5. b) X.-F. Wang, O. Kitao, H. Zhou, H. Tamiaki, S. Sasaki, Chem. Commun. 2009, 1523.
6. c) X.-F. Wang, O. Kitao, H. Zhou, H. Tamiaki, S. Sasaki, J. Phys. Chem. C 2009, 113, 7954.
7. a) T. Miyatake, H. Tamiaki, J. Photochem. Photobiol., C 2005, 6, 89.
8. b) T. S. Balaban, H. Tamiaki, A. R. Holzwarth, Top. Curr. Chem. 2005, 258, 1.
9. c) V. Huber, S. Sengupta, F. Würthner, Chem.-Eur. J. 2008, 14, 7791.
10. d) H. Tamiaki, Y. Kotegawa, S. Nitta, S. Sasaki, K. Mizutani, Tetrahedron 2009, 65, 628.
11. a) S. Sasaki, Y. Kotegawa, H. Tamiaki, Tetrahedron Lett. 2006, 47, 4849.
12. b) S. Sasaki, Y. Kotegawa, H. Tamiaki, Bull. Chem. Soc. Jpn. 2009, 82, 267.
13. Other examples of functional dyes possessing a trifluoro-acetyl group: a) G. J. Mohr, C. Demuth, U. E. Spichiger-Keller, Anal. Chem. 1998, 70, 3868.
14. b) G. J. Mohr, Sens. Actuators, B 2003, 90, 31.
15. c) S. Sasaki, G. Monma, D. Citterio, K. Yamada, K. Suzuki, Chimia 2005, 59, 204.
16. d) Y. M. Chung, B. Raman, D.-S. Kim, K. H. Ahn, Chem. Commun. 2006, 186.
17. e) D. Ryu, E. Park, D.-S. Kim, S. Yan, J. Y. Lee, B.-Y. Chang, K. H. Ahn, J. Am. Chem. Soc. 2008, 130, 2394.
18. Examples of thermochromic dyes: a) V. I. Minkin, Chem. Rev. 2004, 104, 2751.
19. b) K. Kita, T. Tokuoka, E. Monno, S. Yagi, H. Nakazumi, T. Mizutani, Tetrahedron Lett. 2006, 47, 1533.
20. c) M. R. di Nunzio, P. L. Gentili, A. Romani, G. Favaro, ChemPhysChem 2008, 9, 768.
21. a) S. Sasaki, T. Mizoguchi, H. Tamiaki, Tetrahedron 2005, 61, 8041.
22. b) S. Sasaki, H. Takebe, T. Mizoguchi, H. Tamiaki, Tetrahedron Lett. 2005, 46, 7687.
23. a) J. Otera, N. Dan-oh, H. Nozaki, J. Org. Chem. 1991, 56, 5307.
24. b) S. Sasaki, H. Tamiaki, Tetrahedron Lett. 2006, 47, 4965.
25. c) H. Tamiaki, T. Michitsuji, R. Shibata, Photochem. Photobiol. Sci. 2008, 7, 1225.
26. 1HNMR spectrum.
27. Supporting Information (SI) is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.
28. -1 respectively (see Ref. 4a).
29. -1 (at 20°C).