A fluorescent photoinduced electron transfer sensor for cations with an off-on-off proton switch

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2237-2240

  De Silva, Saliya A ^a   Zavaleta, Andres ^a   Baron, David E ^a   Allam, Osama ^a   Isidor, Edward V ^a   Kashimura, Norie ^a   Percarpio, James M ^a  

^a MONTCLAIR STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; ZINC COMPLEX;

ARTICLE; ELECTRON TRANSPORT; FLUORESCENCE; PHOTOCHEMISTRY;

EID: 0031592610     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00332-8     Document Type: Article

References (24)

1. 1. a) Bissell, R. A.; de Silva, A. P.; Gunaratne, H. Q. N.; Lynch, P. L. M.; Maguire, G. E. M.; McCoy, C. P.; Sandanayake, K. R. A. S. Top. Curr. Chem. 1993, 168, 223-264;
2. b) Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302-308;
3. c) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 197-202.
4. 2. a) Huston, M. E.; Haider, K. W.; Czarnik, A. W. J. Am. Chem. Soc. 1988, 110, 4460-4462;
5. b) Fabbrizzi, L.; Licchelli, M.; Pallavicini, P.; Perotti, A.; Taglietti, A.; Sacchi, D. Chem. Eur. J. 1996, 2, 75-82;
6. c) Ghosh, G.; Bharadwaj, P. K.; Mandal, S.; Ghosh, S. J. Am. Chem. Soc. 1996, 118, 1553-1554.
7. 3. a) Bis(2-picolyl)amine was alkylated in 80% yield with 9-chloromethyl anthracene using a general procedure: Hazell, A.; Jensen, K. B.; McKenzie, C. J.; Toftlund, H. J. Chem. Soc. Dalton Trans. 1993, 3249-3257;
8. b) 9-Anthrylmethyl-bis(2-picolyl)amine was reported recently in an unrelated application: Bhattacharya, S.; Mandal, S. S. J. Chem. Soc. Chem. Commun. 1996, 1515-1516.
9. 4. The zinc (II) complex of 1 was prepared in 47% yield by following Czarnik's synthesis of a zinc chelate and was recrystallized from acetonitrile: Nanjappan, P.; Czarnik, A. W. J. Am. Chem. Soc. 1987, 109, 1826-1833.
10. 5. Satisfactory analytical data were obtained for both the sensor and its zinc (II) complex.
11. 6. a) Bissell, R. A.; Calle, E.; de Silva, A. P.; de Silva, S. A.; Gunaratne, H. Q. N.; Habib-Jiwan, J-L.; Peiris, S. L. A.; Rupasinghe, R. A. D. D.; Samarasinghe, T. K. S. D.; Sandanayake, K. R. A. S.; Soumillion, J-P. J. Chem. Soc. Perkin Trans. 2 1992, 1559-1564;
12. -5 M) of 9-methylanthracene and ethyl-bis(2-picolyl)amine.
13. 7. Siegerman, H. In Techniques of Electroorganic Synthesis, Part II; Weinberg, N. L. Ed.; Wiley: New York, 1975, p. 667.
14. 8. a) de Silva, A. P.; Gunaratne, H. Q. N.; Lynch, P. L. M. J. Chem. Soc. Perkin Trans. 2 1995, 685-690;
15. b) Mattes, S. L.; Farid. S. In Organic Photochemistry; Padwa. A. Ed.; M. Dekker: New York, 1983, p. 238;
16. c) For leading references to photoinduced electron transfer see: Fox, M. A.; Channon, M., Eds.; Photoinduced Electron Transfer, Parts A-D; Elsevier: Amsterdam, 1988.
17. 9. a) Calculated as described in: de Silva, A. P.; Gunaratne, H. Q. N.; Maguire, G. E. M. J. Chem. Soc. Chem. Commun. 1994, 1213-1214;
18. b) These values are in agreement with other experimental observations (ref. 6a and 8a);
19. abs = 258 nm) as the ligand was 5.2.
20. 10. a) Leaver, I. H.; Rivett, D. E. Mol. Photochem. 1974, 6, 113-123;
21. b) Maciejewski, A.; Steer, R. P. J. Photochem. 1986, 55, 59-69.
22. 11. For other recent examples of fluorescent zinc sensors see: a) Walkup, G. K.; Imperiali, B. J. Am. Chem. Soc. 1996, 118, 3053-3054;
23. b) Godwin, H. A.; Berg, J. M. J. Am. Chem. Soc. 1996, 118, 6514-6515.
24. 12. An independently developed sensor which operates on the same principle, but responsive only towards protons was reported recently: de Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. J. Chem. Soc. Chem. Commun. 1996, 2399-2400.