The pH-dependent fluorescence of pyridylmethyl-4-amino-1,8-naphthalimides

Arkivoc

Volumn 2003, Issue 7, 2003, Pages 229-243

  De Silva, A Prasanna ^a   Goligher, Anne ^a   Gunaratne, H Q Nimal ^a   Rice, Terence E ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

Excited state intramolecular proton transfer; Fluorescence; Internal charge transfer; Molecular scale electric field; pH sensing; Photoinduced electron transfer

Indexed keywords

N (2' PYRIDYLMETHYL) 4 BUTYLAMINO 1,8 NAPHTHALIMIDE; N (3' PYRIDYLMETHYL) 4 BUTYLAMINO 1,8 NAPHTHALIMIDE; N (4' PYRIDYLMETHYL) 4 BUTYLAMINO 1,8 NAPHTHALIMIDE; N BUTYL 4 (2' PYRIDYLMETHYLAMINO) 1,8 NAPHTHALIMIDE; N BUTYL 4 (3' PYRIDYLMETHYLAMINO) 1,8 NAPHTHALIMIDE; N BUTYL 4 (4' PYRIDYLMETHYLAMINO) 1,8 NAPHTHALIMIDE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; ELECTRIC FIELD; ELECTRON TRANSPORT; ELECTRONIC SENSOR; FLUORESCENCE ANALYSIS; HYDROGEN BOND; PH; PROTON TRANSPORT; SYNTHESIS; THERMODYNAMICS;

EID: 3242678723     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (51)

1. 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.
2. Bissell, R.A.; de Silva, A.P.; Gunaratne, H.Q.N.; Lynch, P.L.M.; Maguire, G.E.M.; Sandanayake, K.R.A.S. Chem. Soc. Rev. 1992, 21, 187.
3. Chemosensors of Ion and Molecule Recognition, Czarnik, A.W., Desvergne, J.-P. (Eds.) Kluwer: Dordrecht, 1997.
4. de Silva, A.P.; Gunaratne, H.Q.N.; Gunnlaugsson, T.; Huxley, A.J.M.; McCoy, C.P.; Rademacher, J.T.; Rice, T.E. Chem. Rev. 1997, 97, 1515.
5. de Silva, A.P.; Rupasinghe, R.A.D.D. J. Chem. Soc., Chem. Commun. 1985, 1669.
6. Czarnik, A.W. Acc. Chem. Res. 1994, 27, 302.
7. Haugland, R.P. Handbook of Fluorescent Probes and Research Chemicals 7th Ed., Molecular Probes, Eugene, OR, 1999.
8. de Silva, A.P.; Gunaratne, H.Q.N.; Lynch, P.L.M. J. Chem. Soc. Perkin Trans. 2 1995, 685.
9. de Silva, A.P.; Gunaratne, H.Q.N.; McCoy, C.P. Chem. Commun. 1996, 2399.
10. de Silva, S.A.; Zavaleta, A.; Baron, D.E.; Allam, O.; Isidor, E.V.; Kashimura, N.; Percarpio, J.M. Tetrahedron Lett. 1997, 38, 2237.
11. Amendola, V.; Fabbrizzi, L.; Pallavicini, P.; Parodi, L.; Perotti, A. J. Chem. Soc. Dalton Trans. 1998, 2053.
12. Valeur, B. Molecular Fluorescence Wiley-VCH, Weinheim, 2001.
13. de Silva, A.P.; Gunaratne, H.Q.N.; Habib-Jiwan, J.-L.; McCoy, C.P.; Rice, T.E.; Soumillion, J.-P. Angew. Chem., Int. Ed. Engl. 1995, 34, 1728.
14. de Silva, A.P.; Rice T.E. Chem. Commun. 1999, 163.
15. Fox, M.A.; Galoppini, E. J. Am. Chem. Soc., 1997, 119, 5277.
16. Gosztola, D.; Niemczyk, M.P.; Wasielewski, M.R. J. Am. Chem. Soc. 1998, 120, 5118.
17. The Photosynthetic Reaction Center, Vols. 1, 2 Deisenhofer, J.; Norris, J.R. (Eds.) Academic Press, San Diego, 1993.
18. Gao, Y.Q.; Marcus, R.A. J. Phys. Chem. A 2002, 106, 1956; Sweeney, R. Personal communication.
19. Gao, Y.Q.; Marcus, R.A. J. Phys. Chem. A 2002, 106, 1956; Sweeney, R. Personal communication.
20. Greenfield, S.R.; Svec, W.A.; Gosztola, D.J.; Wasielewski, M.R. J. Am. Chem. Soc. 1996, 118, 6767.
21. Greenfield, S.R.; Svec, W.A.; Gosztola, D.J.; Wasielewski, M.R. New J. Chem. 1996, 20, 815.
22. Hasharoni, K.; Levanon, H.; Greenfield, S.R.; Gosztola, D.J.; Svec, W.A.; Wasielewski, M.R. J. Am. Chem. Soc. 1996, 118, 10228.
23. Ni, W.J.; Su, J.H.; Chen, K.C.; Tian, H. Chem. Lett., 1997, 101.
24. Ramachandram, B.; Samanta, A. Chem. Commun. 1997, 1037.
25. Mitchell, K.A.; Brown, R.G.; Yuan, D.; Chang, S-C.; Utecht, R.E.; Lewis, D.E. J. Photochem. Photobiol. A: Chem. 1998, 115, 157.
26. Grabchev, I. Dyes Pigm. 1998, 38, 219.
27. de Silva, A.P.; Gunaratne, H.Q.N.; Gunnlaugsson, T. Tetrahedron Lett. 1998, 39, 5077.
28. Cosnard, F.; Wintgens, V. Tetrahedron Lett. 1998, 39, 2752.
29. Ramachandram, B.; Sankaran, N.B.; Samanta, A. Res. Chem. Intermed. 1999, 25, 843.
30. Tian, H.; Xu, T.; Zhao, Y.; Chen, K.C. J. Chem. Soc. Perkin Trans. 2, 1999, 545.
31. Ramachandram, B.; Saroja, G.; Sankaran, N.B.; Samanta, A. J. Phys. Chem. B 2000, 104, 11824.
32. Qian, X.; Xiao, Y. Tetrahedron Lett. 2002, 43, 2991.
33. Grabchev, I.; Qian, X.H.; Xiao, Y.; Zhang, R. New J. Chem. 2002, 26, 921.
34. Grabchev, I.; Qian, X.H.; Bojinov, V.; Xiao, Y.; Zhang, W. Polymer, 2002, 43, 5731.
35. Badugu, R. Chem. Lett. 2002, 106, 5572.
36. Saha, S.; Samanta, A. J. Phys. Chem. A 2002, 106, 4763.
37. He, H.; Mortellaro, M. A.; Leiner, M. J. P.; Young, S. T.; Fraatz, R. J.; Tusa, J. K. Anal. Chem., 2003, 75, 549.
38. He, H.; Mortellaro, M. A.; Leiner, M. J. P.; Fraatz, R. J.; Tusa, J. K. J. Am. Chem. Soc. 2003, 125, 1468.
39. Siegerman, H. in Techniques of Electroorganic Synthesis. Part II Weinberg, N.L. (Ed.) Wiley, New York, 1975, p. 667.
40. McCoy, C.P. Ph.D. Thesis, Queen's University, Belfast, 1994.
41. Alexiou, M.S.; Tychopoulos, V.; Ghorbanian, S.; Tyman, J.H.p.; Brown, R.G.; Brittain, P.I. J. Chem. Soc. Perkin Trans. 2 1990, 837.
42. Xuhong, Q.; Zhenghua, Z.; Chen, K.C. Dyes Pigm. 1989, 11, 13.
43. Daffy, L.M.; de Silva, A.P.; Gunaratne, H.Q.N.; Huber, C.; Lynch, P.L.M.; Werner, T.; Wolfbeis, O.S. Chem. Eur. J. 1998, 4, 1810.
44. Pardo, A.; Campanario, J.; Poyato, J.M.L.; Camacho, J.J.; Reyman, D.; Martin, E. J. Mol. Struct. (Theochem) 1988, 166, 463.
45. de Silva, A.P.; Gunaratne, H.Q.N.; Lynch, P.L.M.; Patty, A.J.; Spence, G.L.J. Chem. Soc. Perkin Trans. 2 1993, 1611.
46. Perrin, D.D. Dissociation Constants of Organic bases in Aqueous Solution, Butterworth, London, 1965; Serjeant, E.P.; Dempsey, B. Ionization Constants of Organic Acids in Aqueous Solution, Pergamon, Oxford, 1979.
47. Perrin, D.D. Dissociation Constants of Organic bases in Aqueous Solution, Butterworth, London, 1965; Serjeant, E.P.; Dempsey, B. Ionization Constants of Organic Acids in Aqueous Solution, Pergamon, Oxford, 1979.
48. Moriya, T. Bull. Chem. Soc. Jpn. 1983, 56, 6.
49. Klopffer, W. Adv. Photochem. 1977, 10, 311.
50. Yuan, D.; Brown, R.G. J. Chem. Res. (S). 1994, 418.
51. Birks, J.B. Photophysics of Aromatic Molecules, Wiley, New York, 1970.