Fluorescent Molecular Thermometers Based on Polymers Showing Temperature-Induced Phase Transitions and Labeled with Polarity-Responsive Benzofurazans

Analytical Chemistry

Volumn 75, Issue 21, 2003, Pages 5926-5935

  Uchiyama, Seiichi ^a,b   Matsumura, Yuriko ^a   De Silva, A Prasanna ^b   Iwai, Kaoru ^a  

^a NARA WOMEN'S UNIVERSITY   (Japan)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COOLING; COPOLYMERS; FLUORESCENCE; HEATING; THERMOMETERS;

SOLVENT POLARITY;

PHASE TRANSITIONS;

4 N (2 ACRYLOXYLOXYETHYL) N METHYLAMINO 7 N,N DIMETHYLAMINOSULFONYL 2,1,3 BENZOXADIAZOLE; ACRYLAMIDE DERIVATIVE; BENZOFURAZAN DERIVATIVE; BENZOXAZOLE DERIVATIVE; ISOPROPYLMETHACRYLAMIDE; POLY(N ISOPROPYLACRYLAMIDE); PROPYLACRYLAMIDE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; COOLING; FLUORESCENCE; HEATING; PHASE TRANSITION; POLARIZATION; POLYMERIZATION; TEMPERATURE SENSITIVITY; THERMOMETER;

EID: 0242291112     PISSN: 00032700     EISSN: None     Source Type: Journal    
DOI: 10.1021/ac0346914     Document Type: Article

References (62)

1. Brasselet, S.; Moerner, W. E. Single Mol. 2000, 1, 17-23.
2. Valeur, B. Molecular Fluorescence; Wiley-VCH: Weinheim, 2002.
3. (a) 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, 1515-1566.
4. (b) Czarnik, A. W.; Desvergne, J.-P. Chemosensors of Ion and Molecule Recognition: Kluwer: Dordrecht, The Netherlands, 1997.
5. (c) Fabbrizzi, L.; Licchelli, M.; Pallavicini, P. Acc. Chem. Res. 1999, 32, 846-853.
6. Toyo'oka, T. Modern Derivatization Methods for Separation Sciences; Wiley: Chichester, U.K., 1999.
7. Haugland, R. P. Handbook of Fluorescent Probes and Research Products, 9th ed.; Molecular Probes: Eugene. OR, 2002.
8. Brown, G. J.; de Silva, A. P.; Pagliari, S. Chem. Commun. 2002, 2461-2463.
9. Balzani, V.; Venturi, M.; Credi, A. Molecular Devices and Machines; Wiley-VCH: Weinheim, 2003.
10. Tour, J. M. Acc. Chem. Res. 2000, 33, 791-804.
11. (a) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611-619.
12. (b) Collier, C. P.; Mattersteig, G.; Wong, E. W.; Luo, Y.; Beverly, K.; Sampaio, J.; Raymo, F. M.; Stoddart, J. F.; Kuekes, P. J.; Williams, R. S.; Heath, J. R. Science 2000, 289, 1172-1175.
13. (c) Brouwer, A. M.; Frochot, C.; Gatti, F. G.; Leigh, D. A.; Mottier, L. ; Paolucci, F.; Roffia, S.; Wurpel, G. W. H. Science 2001, 291, 2124-2128.
14. Chapman, C. F.; Liu, Y.; Sonek, G. J.; Tromberg, B. J. Photochem. Photobiol. 1995, 62, 416-425.
15. Chandrasekharan, N.; Kelly, L. A. J. Am. Chem. Soc. 2001, 123, 9898-9899.
16. Brewster, R. E.; Kidd, M. J.; Schuh, M. D. Chem. Commun. 2001, 1134-1135.
17. Figueroa, I. D.; El Baraka, M.; Quiñones, E.; Rosario, O.; Deumié, M. Anal. Chem. 1998, 70, 3974-3977.
18. Engeser, M.; Fabbrizzi, L.; Licchelli, M.; Sacchi, D. Chem. Commun. 1999, 1191-1192.
19. Lou, J.; Hatton, T. A.; Laibinis, P. E. Anal. Chem. 1997, 69, 1262-1264.
20. Schrum, K. F.; Williams, A. M.; Haerther, S. A.; Ben-Amotz, D. Anal. Chem. 1994, 66, 2788-2790.
21. de Silva, A. P.; Gunaratne, H. Q. N.; Jayasekera, K. R.; O'Callaghan, S. ; Sandanayake, K. R. A. S. Chem. Lett. 1995, 123-124.
22. Sabbatini, N.; Guardigli, M.; Bolletta, F.; Manet, I.; Ziessel, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1501-1504.
23. Leiner, M. J. P.; He, H.; Boila-Gockel, A. U.S. Patent 5,952,491, 1999.
24. Taylor, L. D.; Cerankowski, L. D. J. Polym. Sci., Polym. Chem. 1975, 13, 2551-2570.
25. Eggert, M.; Freitag, R. J. Polym. Sci., Polym. Chem. 1994, 32, 803-813.
26. Winnik, F. M. Macromolecules 1990, 23, 233-242.
27. McQuade, D. T.; Hegedus, A. H.; Swager, T. M. J. Am. Chem. Soc. 2000, 122, 12389-12390.
28. Whitten, D.; Jones, R.; Bergstedt, T.; McBranch, D.; Chen, L.; Heeger, P. In Optical Sensors and Switches; Ramamurthy, V., Schanze, K. S., Eds.; Dekker, New York, 2001; pp 189-208.
29. Vogtle, F.; Gestermann, S.; Kauffmann, C.; Ceroni, P.; Vicinelli, V.; Balzani, V. J. Am. Chem. Soc. 2000, 122, 10398-10404.
30. Schild, H. G. Prog. Polym. Sci. 1992, 17, 163-249.
31. Iwai, K.; Matsumoto, N.; Niki, M.; Yamamoto, M. Mol. Cryst. Liq. Cryst. 1998, 315, 53-58.
32. Chee, C. K.; Rimmer, S.; Soutar, I.; Swanson, L. Polymer 2001, 42, 5079-5087.
33. Fang, Y.; Qiang, J. C.; Hu, D. D.; Wang, M. Z.; Cui, Y. L. Colloid Polym. Sci. 2001, 279, 14-21.
34. For a recent review, see: Uchiyama, S.; Santa, T.; Okiyama, N.; Fukushima, T.; Imai, K. Biomed. Chromatogr. 2001, 15, 295-318. For recent progress, see: (a) Onoda, M.; Uchiyama, S.; Endo, A.; Tokuyama, H.; Santa, T.; Imai, K. Org. Lett. 2003, 5, 1459-1461.
35. For a recent review, see: Uchiyama, S.; Santa, T.; Okiyama, N.; Fukushima, T.; Imai, K. Biomed. Chromatogr. 2001, 15, 295-318. For recent progress, see: (a) Onoda, M.; Uchiyama, S.; Endo, A.; Tokuyama, H.; Santa, T.; Imai, K. Org. Lett. 2003, 5, 1459-1461.
36. (b) Vogel, M.; Karst, U. Anal. Chem. 2002, 74, 6418-6426.
37. Uchiyama, S.; Santa, T.; Imai, K. J. Chem. Soc., Perkin Trans. 2 1999, 2525-2532.
38. (a) Uchiyama, S.; Santa, T.; Imai, K. Anal. Chem. 2001, 73, 2165-2170.
39. (b) Uchiyama, S.; Santa, T.; Suzuki, S.; Yokosu, H.; Imai, K. Anal. Chem. 1999, 71, 5367-5371.
40. Chee, C. K.; Rimmer, S.; Shaw, D. A.; Soutar, I.; Swanson, L. Macromolecules 2001, 34, 7544-7549.
41. (a) Ito, S. Kobunshi Ronbunshu 1989, 46, 437-443.
42. (b) Ringsdorf, H.; Venzmer, J.; Winnik, F. M. Macromolecules 1991, 24, 1678-1686.
43. Uchiyama, S.; Santa, T.; Fukushima, T.; Homma, H.; Imai, K. J. Chem. Soc., Perkin Trans. 2 1998, 2165-2173.
44. Onoda, M.; Uchiyama, S.; Santa, T.; Imai, K. Anal. Chem. 2002, 74, 4089-4096.
45. Yamazaki, A.; Song, J. M.; Winnik, F. M.; Brash, J. L. Macromolecules 1998, 31, 109-115.
46. Winnik, F. M.; Tamai, N.; Yonezawa, J.; Nishimura, Y.; Yamazaki, I. J. Phys. Chem. 1992, 96, 1967-1972.
47. Fery-Forgues, S.; Fayet, J. P.; Lopez, A. J. Photochem. Photobiol. A: Chem. 1993, 70, 229-243.
48. Schild, H. G.; Tirrell, D. A. J. Phys. Chem. 1990, 94, 4352-4356.
49. Fujishige, S.; Kubota, K.; Ando, I. J. Phys. Chem. 1989, 93, 3311-3313.
50. (a) Shibanuma, T.; Aoki, T.; Sanui, K.; Ogata, N.; Kikuchi, A.; Sakurai, Y.; Okano, T. Macromolecules 2000, 33, 444-450.
51. (b) Charalambopoulou, A.; Bokias, G.; Staikos, G. Polymer 2002, 43, 2637-2643.
52. (a) Schild, H. G.; Muthukumar, M.; Tirrell, D. A. Macromolecules 1991, 24, 948-952.
53. (b) Winnik, F. M.; Ringsdorf, H.; Venzmer, J. Macromolecules 1990, 23, 2415-2416.
54. (a) Eeckman, F.; Moës, A. J.; Amighi, K. Int. J. Pharm. 2002, 241, 113-125.
55. (b) Winnik, F. M.; Adronov, A.; Kitano, H. Can. J. Chem. 1995, 73, 2030-2040.
56. (a) Knyukshto, V. N.; Avlasevich, Y. S.; Kulinkovich, O. G.; Solovyov, K. N. J. Fluorescence 1999, 9, 371-378.
57. (b) Chee, C. K.; Rimmer, S.; Soutar, I.; Swanson, L. Polymer 1997, 38, 483-486.
58. Li, M.; Jiang, M.; Zhang, Y.; Fang, Q. Macromolecules 1997, 30, 470-478.
59. (a) Melo, J. S.; Becker, R. S.; Elisei, F.; Maçanita, A. L. J. Chem. Phys. 1997, 107, 6062-6069.
60. (b) Elisei, F.; Aloisi, G. G.; Dall'Acqua, F.; Latterini, L.; Masetti, F.; Rodighiero, P. Photochem. Photobiol. 1998, 68, 164-172.
61. (c) Azuma, K.; Suzuki, S.; Uchiyama, S.; Kajiro, T.; Santa, T.; Imai, K. Photochem. Photobiol. Sci. 2003, 2, 443-449.
62. Kellmann, A. J. Phys. Chem. 1977, 81, 1195-1198.