Chromophore-derivatized semifluorinated polymers for colorimetric and turn-on fluorescent anion detection

Sensors and Actuators, B: Chemical

Volumn 143, Issue 1, 2009, Pages 1-5

  Gilliard Jr , Robert J ^a   Iacono, Scott T ^a   Budy, Stephen M ^a   Moody, Justin D ^a   Smith Jr , Dennis W ^a   Smith, Rhett C ^a  

^a AMRL   (United States)

Author keywords

Colorimetric sensor; Cyanide; Fluorescent sensor; Fluoride; Fluoropolymer

Indexed keywords

ANION SENSORS; COLORIMETRIC CHANGE; COLORIMETRIC SENSOR; COLORIMETRIC SENSORS; DISSOCIATION CONSTANT; DISTYRYLBENZENE DERIVATIVES; FLUORESCENT SENSORS; FLUOROPOLYMER; MAIN CHAINS; PHOTOLUMINESCENCE ENHANCEMENT; RESPONSIVE POLYMER;

CHROMOPHORES; COLOR; COLORIMETRY; CONJUGATED POLYMERS; CYANIDES; DISSOCIATION; FLUORESCENCE; NEGATIVE IONS; PHOTORESISTS; SENSORS; TRANSITION METALS;

POLYMERS;

EID: 71849087368     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2009.08.047     Document Type: Article

References (70)

1. Martinez-Manez R., and Sancenon F. Chem. Rev. 103 (2003) 4419-4476
2. Anslyn E.V. J. Org. Chem. 72 (2007) 687-699
3. Snowden T.S., and Anslyn E.V. Curr. Opin. Chem. Biol. 3 (1999) 740-746
4. Anzenbacher Jr. P., and Jursikova K. Fluoresc. Sens. Biosens. (2006) 219-231
5. Czarnik A.W. Chem. Biol. 2 (1995) 423-428
6. Czarnik A.W. Topics Fluor. Spec. 4 (1994) 49-70
7. Amendola V., Bonizzoni M., Esteban-Gomez D., Fabbrizzi L., Licchelli M., Sancenon F., and Taglietti A. Coord. Chem. Rev. 250 (2006) 1451-1470
8. Amendola V., Esteban-Gomez D., Fabbrizzi L., and Licchelli M. Acc. Chem. Res. 39 (2006) 343-353
9. Sessler J.L., Lawrence C.M., and Jayawickramarajah J. Chem. Soc. Rev. 36 (2007) 314-325
10. Katayev E.A., Ustynyuk Y.A., and Sessler J.L. Coord. Chem. Rev. 250 (2006) 3004-3037
11. Sessler J.L., Camiolo S., and Gale P.A. Coord. Chem. Rev. 240 (2003) 17-55
12. Browne D., Whelton H., and O'Mullane D. J. Dent. 33 (2005) 177-186
13. Fomon S.J., Ekstrand J., and Ziegler E.E. J. Public Health Dent. 60 (2000) 131-139
14. Aaseth J., Shimshi M., Gabrilove J.L., and Birketvedt G.S. J. Trace Elem. Med. Biol. 17 (2004) 83-92
15. Kleerekoper M. Crit. Rev. Clin. Lab. Sci. 33 (1996) 139-161
16. Yang Y.-C., Baker J.A., and Ward J.R. Chem. Rev. 92 (1992) 1729-1743
17. Knapton D., Burnworth M., Rowan S.J., and Weder C. Angew. Chem. Int. Ed. 45 (2006) 5825-5829
18. Bencic-Nagale S., Sternfeld T., and Walt D.R. J. Am. Chem. Soc. 128 (2006) 5041-5048
19. Zhang S.-W., and Swager T.M. J. Am. Chem. Soc. 125 (2003) 3420-3421
20. Anzenbacher Jr. P., Try A.C., Miyaji H., Jursikova K., Lynch V.M., Marquez M., and Sessler J.L. J. Am. Chem. Soc. 122 (2000) 10268-10272
21. Ghosh K., and Adhikari S. Tetrahedron Lett. 47 (2006) 8165-8169
22. Nishiyabu R., and Anzenbacher Jr. P. Org. Lett. 8 (2006) 359-362
23. Nishiyabu R., Palacios M.A., Dehaen W., and Anzenbacher Jr. P. J. Am. Chem. Soc. 128 (2006) 11496-11504
24. Lin Z.-H., Zhao Y.-G., Duan C.-Y., Zhang B.-G., and Bai Z.-P. Dalton Trans. (2006) 3678-3684
25. Badugu R., Lakowicz J.R., and Geddes C.D. Sens. Act. B B104 (2005) 103-110
26. Anzenbacher Jr. P., Palacios M.A., Jursikova K., and Marquez M. Org. Lett. 7 (2005) 5027-5030
27. Badugu R., Lakowicz J.R., and Geddes C.D. Curr. Anal. Chem. 1 (2005) 157-170
28. Anzenbacher P., Jursikova K., Aldakov D., Marquez M., and Pohl R. Tetrahedron 60 (2004) 11163-11168
29. Badugu R., Lakowicz J.R., and Geddes C.D. J. Fluoresc. 14 (2004) 693-703
30. Tong H., Wang L., Jing X., and Wang F. Macromolecules 36 (2003) 2584-2586
31. Zhang S., Palkar A., and Echegoyen L. Langmuir 22 (2006) 10732-10738
32. Black C.B., Andrioletti B., Try A.C., Ruiperez C., and Sessler J.L. J. Am. Chem. Soc. 121 (1999) 10438-10439
33. Yamaguchi S., Akiyama S., and Tamao K. J. Am. Chem. Soc. 122 (2000) 6793-6794
34. Kim T.-H., and Swager T.M. Angew. Chem. Int. Ed. 42 (2003) 4803-4806
35. Melaimi M., and Gabbai Francois P. J. Am. Chem. Soc. 127 (2005) 9680-9681
36. Lee M.H., Agou T., Kobayashi J., Kawashima T., and Gabbai F.P. Chem. Commun. (2007) 1133-1135
37. Sole S., and Gabbai F.P. Chem. Commun. (2004) 1284-1285
38. Yamaguchi S., Akiyama S., and Tamao K. J. Am. Chem. Soc. 123 (2001) 11372-11375
39. Ayoob S., and Gupta A.K. Crit. Rev. Environ. Sci. Technol. 36 (2006) 433-487
40. Crenshaw B.R., Burnworth M., Khariwala D., Hiltner A., Mather P.T., Simha R., and Weder C. Macromolecules 40 (2007) 2400-2408
41. Kunzelman J., Crenshaw B.R., Kinami M., and Weder C. Macromol. Rapid Commun. 27 (2006) 1981-1987
42. Kinami M., Crenshaw B.R., and Weder C. Chem. Mater. 18 (2006) 946-955
43. Crenshaw B.R., and Weder C. Adv. Mater. 17 (2005) 1471-1476
44. Lowe C., and Weder C. Adv. Mater. 14 (2002) 1625-1629
45. Hock J., Cargill-Thompson A.M.W., McClevery J.A., and Ward M.D. Dalton Trans. (1996) 4257
46. Chen Y., Hwang S.-W., and Yu Y.-H. Polymer 44 (2003) 3827
47. M. J. Plater, T. Jackson, Tetrahedron 59, 4673.
48. Iacono S.T., Budy S.M., Ewald D., and Smith Jr. D.W. Chem. Commun. (2006) 4844-4846
49. Bis(trifluorovinyloxy)arenes are available from Tetramer Technologies, L.L.C.: www.tetramertechnologies.com.
50. See Supplementary Information.
51. Hammond P.R. J. Chem. Soc. (1964) 479-484
52. Aldakov D., and Anzenbacher Jr. P. J. Am. Chem. Soc. 126 (2004) 4752-4753
53. Fan L.-J., Zhang Y., and Jones Jr. W.E. Macromolecules 38 (2005) 2844-2849
54. Fan L.-J., and Jones Jr. W.E. J. Am. Chem. Soc. 128 (2006) 6784-6785
55. Smith R.C., Tennyson A.G., Lim M.H., and Lippard S.J. Org. Lett. 7 (2005) 3573-3575
56. Nolan E.M., and Lippard S.J. Inorg. Chem. 43 (2004) 8310-8317
57. Lim M.H., Xu D., and Lippard S.J. Nature Chem. Biol. 2 (2006) 375-380
58. Chang C.J., Jaworski J., Nolan E.M., Sheng M., and Lippard S.J. Proc. Natl. Acad. Sci., USA 101 (2004) 1129-1134
59. Bredas J.L., Cornil J., and Heeger A.J. Adv. Mater. 8 (1996) 447-452
60. Lemmer U., Heun S., Mahrt R.F., Scherf U., Hopmeier M., Siegner U., Goebel E.O., Muellen K., and Baessler H. Chem. Phys. Lett. 240 (1995) 373-378
61. Hernandez V., Castiglioni C., Del Zoppo M., and Zerbi G. Phys. Rev. B: Condens. Matter. 50 (1994) 9815-9823
62. Liu B., Yu W.-L., Pei J., Liu S.-Y., Lai Y.-H., and Huang W. Macromolecules 34 (2001) 7932-7940
63. Coles S.J., Gale P.A., Hursthouse M.B., Light M.E., and Warriner C.N. Supramolecular Chem. 16 (2004) 469-486
64. Gale P.A., Hursthouse M.B., Light M.E., and Warriner C.N. Collect. Czech. Chem. Commun. 69 (2004) 1301-1308
65. Hartmann H., Eckert K., and Schroder A. Angew. Chem. Int. Ed. 39 (2000) 556-558
66. Spange S., Reuter A., and Vilsmeier E. Colloid Polym. Sci. 274 (1996) 59-69
67. Ramirez C.B., Carrasco N., and Rezende M.C. J. Chem. Soc., Faraday Trans. 91 (1995) 3839-3842
68. Effenberger F., Wuerthner F., and Steybe F. J. Org. Chem. 60 (1995) 2082-2091
69. Belletete M., Leclerc M., and Durocher G. J. Phys. Chem. 98 (1994) 9450-9456
70. 19F NMR spectroscopy.