Fluorescence enhancement of Di-p-tolyl viologen by complexation in cucurbit[7]uril

Journal of the American Chemical Society

Volumn 134, Issue 7, 2012, Pages 3358-3366

  Freitag, Marina ^a   Gundlach, Lars ^a,b   Piotrowiak, Piotr ^a   Galoppini, Elena ^a  

^a RUTGERS UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION AND EMISSION SPECTRA; AG/AGCL; BIPYRIDINES; BLUE-SHIFTED; COMPLEXATION CONSTANTS; CONFIGURATION INTERACTION SINGLES; CUCURBIT[7]URIL; ELECTRON ACCEPTOR; EMISSION ENHANCEMENT; ENHANCED FLUORESCENCE; FINE STRUCTURES; FLUORESCENCE ENHANCEMENT; MACROCYCLICS; POLY(METHYL METHACRYLATE) MATRIX; ROTATIONAL RELAXATIONS; STOKES SHIFT; VIOLOGENS;

EMISSION SPECTROSCOPY; ESTERS; SODIUM CHLORIDE; SOLUTIONS; WATER ABSORPTION;

FLUORESCENCE;

CUCURBIT[7]URIL; MACROCYCLIC COMPOUND; NANOMATERIAL; POLY(METHYL METHACRYLATE); POLYMER; SODIUM; UNCLASSIFIED DRUG; VIOLOGEN;

AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; ELECTRON; ENCAPSULATION; FLUORESCENCE ANALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; TITRIMETRY; ULTRAVIOLET RADIATION;

EID: 84857426981     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja206833z     Document Type: Article

References (75)

1. Monk, P. M. S. The Viologens: Physicochemical Properties, Synthesis and Applications of the Salts of 4,4′-Bipyridine; Wiley: New York, 1998.
2. Cinnsealach, R.; Boschloo, G.; Rao, S. N.; Fitzmaurice, D. Sol. Energy Mater. Sol. Cells 1998, 55, 215-218
3. Campus, F.; Bonhote, P.; Grätzel, M.; Heinen, S.; Walder, L. Sol. Energy Mater. Sol. Cells 1999, 56, 281-297
4. Cummins, D.; Boschloo, G.; Ryan, M.; Corr, D.; Rao, S. N.; Fitzmaurice, D. J. Phys. Chem. B 2000, 104, 11449-11459
5. Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H. J.; Kim, K. Acc. Chem. Res. 2003, 36, 621-630
6. Flood, A. H.; Stoddart, J. F.; Steuerman, D. W.; Heath, J. R. Science 2004, 306, 2055-2061
7. Luo, Y.; Collier, C. P.; Jeppesen, J. O.; Nielsen, K. A.; DeIonno, E.; Ho, G.; Perkins, J.; Tseng, H.-R.; Yamamoto, T.; Stoddart, J. F.; Heath, J. R. ChemPhysChem 2002, 3, 519-525
8. Smith, E. A.; Lilienthal, R. R.; Fonseca, R. J.; Smith, D. K. Anal. Chem. 1994, 66, 3013-3020
9. Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71
10. Pía, E.; Toba, R.; Chas, M.; Peinador, C.; Quintela, J. M. Tetrahedron Lett. 2006, 47, 1953-1956
11. Ploug-Sørensen, A.; Nielsen, M. B.; Becher, J. Tetrahedron Lett. 2003, 44, 2979-2982
12. Benniston, A. C. Chem. Soc. Rev. 2004, 33, 573-578
13. Ramaiah, D.; Neelakandan, P. P.; Nair, A. K.; Avirah, R. R. Chem. Soc. Rev. 2010, 39, 4158-4168
14. Park, J. W.; Song, H. J.; Chang, H.-J. Tetrahedron Lett. 2006, 47, 3831-3834
15. Long, B.; Nikitin, K.; Fitzmaurice, D. J. Am. Chem. Soc. 2003, 125, 15490-15498
16. Qu, D.-H.; Tian, H. Chem. Sci. 2011, 2, 1011-1015
17. Nepogodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98, 1959-1976
18. Trabolsi, A.; Khashab, N.; Fahrenbach, A. C.; Friedman, D. C.; Colvin, M. T.; Cotí, K. K.; Benítez, D.; Tkatchouz, E.; Olsen, J.-C.; Belowich, M. E.; Carmielli, R.; Khatib, H. A.; Goddard, W. A., III; Wasielewski, M. R.; Stoddart, J. F. Nat. Chem. 2010, 2, 42-49
19. Coronado, E.; Gavin, P.; Tatay, S. Chem. Soc. Rev. 2009, 38, 1674-1689
20. Holmlin, R. E.; Dandliker, P. J.; Barton, J. K. Angew. Chem., Int. Ed. Engl. 1997, 36, 2714-2730
21. Balzani, V. Electron Transfer in Chemistry; Wiley-VCH: Weinheim, Germany, 2008.
22. Yonemoto, E. H.; Saupe, G. B.; Schmehl, R. H.; Stefan, S.; Hubig, M.; Riley, R. L.; Iverson, B. L.; Mallouk, T. E. J. Am. Chem. Soc. 1994, 116, 4786-4795
23. Nelissen, H. F. M.; Kercher, M.; De Cola, L.; Feiters, M. C. R.; Nolte, J. M. Chem.-Eur. J. 2002, 8, 5407-5414
24. Esswein, A. J.; Nocera, D. G. Chem. Rev. 2007, 107, 4022-4047
25. Youngblood, W. J.; Lee, S.-H. A.; Maeda, K.; Mallouk, T. E. Acc. Chem. Res. 2009, 42, 1966-1973
26. Clennan, E. L. Coord. Chem. Rev. 2004, 248, 477-492
27. Da Silva, S.; Cosnier, S.; Almeida, M. G.; Moura, J. J. G. Electrochem. Commun. 2004, 6, 404-408
28. Liu, X.; Neoh, K. G.; Cen, L.; Kang, E. T. Biosens. Bioelectron. 2004, 19, 823-834
29. Steed, J. W.; Atwood, J. L. Supramolecular Chemistry, 2 nd ed.; Wiley: Chichester, U.K., 2009.
30. Kim, K.; Selvapalam, N.; Oh, D. H. J. Inclusion Phenom. Macrocyclic Chem. 2004, 50, 31-36
31. Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844-4870
32. Sindelar, V.; Silvi, S.; Kaifer, A. E. Chem. Commun. 2006, 2185-2187
33. Kim, H. J.; Jeon, W. S.; Ko, Y. H.; Kim, K. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5007-5011
34. Kim, K.; Selvapalam, N.; Ko, Y. H.; Park, K. M.; Kim, D.; Kim, K. J. Chem. Soc. Rev. 2007, 36, 267-279
35. Freitag, M.; Galoppini, E. Langmuir 2010, 26, 8262-8269
36. Kavarnos, G. J.; Turro, N. J. Chem. Rev. 1986, 86, 401-449
37. Haeupl, T.; Lomoth, R.; Hammarström, L. J. Phys. Chem. A 2003, 107, 435-438
38. Clark, C. D.; Debad, J. D.; Yonemoto, E. H.; Mallouk, T. E.; Bard, A. J. J. Am. Chem. Soc. 1997, 119, 10525-10531
39. Alvaro, M.; Garcia, H.; Garcia, S.; Marquez, F.; Scaiano, J. C. J. Phys. Chem. B 1997, 101, 3043-3051
40. Barnett, J. R.; Hopkins, A. S.; Ledwith, A. J. Chem. Soc., Perkin Trans. 2 1973, 80-84
41. Ebbesen, T. W.; Manring, L. E.; Peters, K. S. J. Am. Chem. Soc. 1984, 106, 7400-7404
42. Novakovic, V.; Hoffman, M. Z. J. Am. Chem. Soc. 1987, 109, 2341-2346
43. Alvaro, M.; Facey, G. A.; García, H.; García, S.; Scaiano, J. C. J. Phys. Chem. 1996, 100, 18173-18176
44. Mau, A. W.-H.; Overbeek, J. M.; Loder, J. W.; Sasse, W. H. F. J. Chem. Soc., Faraday Trans. 2 1986, 82, 869-876
45. Peon, J.; Tan, X.; Hoerner, J. D.; Xia, C.; Luk, Y. F.; Kohler, B. J. Phys. Chem. A 2001, 105, 5768-5777
46. Marquez, C.; Huang, F.; Nau, W. M. IEEE Trans. Nanobiosci. 2004, 3, 39-45
47. Koner, A. L.; Nau, W. M. Supramol. Chem. 2007, 19, 55-66
48. Parvari, G.; Reany, O.; Keinan, E. Isr. J. Chem. 2011, 51, 646-663
49. Metrangolo, P.; Resnati, G. In Encyclopedia of Supramolecular Chemistry; Atwood, J. L.; Steed, J. W., Eds.; Marcel Dekker: New York, 2004.
50. Wang, R.; Yuan, L.; Macartney, D. H. J. Org. Chem. 2006, 71, 1237-1239
51. Freitag, M.; Galoppini, E. Energy Environ. Sci. 2011, 4, 2482-2494
52. Maddlipata, M. V. S. N.; Kaanumalle, L. S.; Natarajan, A.; Pattabiraman, M.; Ramamurthy, V. Langmuir 2007, 23, 7545-7554
53. Marquez, C.; Hudgins, R. R.; Nau, W. M. J. Am. Chem. Soc. 2004, 126, 5806-5816
54. Megyesi, M.; Biczók, L.; Jablonkai, I. J. Phys. Chem. C 2008, 112, 3410-3416
55. Shaikh, M.; Mohanty, J.; Bhasikuttan, A. C.; Uzunova, V. D.; Nau, W. M.; Pal, H. Chem. Commun. 2008, 3681-3683
56. Rekharsky, M. V.; Inoue, Y. Netsu Sokutei 2007, 34, 232-243
57. Khan, M. S. A.; Heger, D.; Necas, M.; Sindelar, V. J. Phys. Chem. B 2009, 113, 11055-11061
58. Bos, F. Appl. Opt. 1981, 20, 3553-3556
59. Gundlach, L.; Piotrowiak, P. Opt. Lett. 2008, 33, 992-994
60. Kamogawa, H.; Satoh, S. J. Polym. Sci., Part A: Polym. Chem. 1988, 26, 653-656
61. Zincke, T. H.; Weisspfenning, G. Justus Liebigs Ann. Chem. 1913, 396, 103-131
62. Kunugi, S.; Okubo, T.; Ise, N. J. Am. Chem. Soc. 1976, 98, 2282-2287
63. Montes-Navajas, P.; Corma, A.; Garcia, H. J. Mol. Catal. A: Chem. 2008, 279, 165-169
64. Moon, K.; Kaifer, A. E. Org. Lett. 2004, 6, 185-188
65. Wang, R.; Bardelang, D.; Waite, M.; Udachin, K. A.; Leek, D. M.; Yu, K.; Ratcliffe, C. I.; Ripmeester, J. A. Org. Biomol. Chem. 2009, 7, 2435-2439
66. Ong, W.; Kaifer, A. E. Angew. Chem., Int. Ed. 2003, 42, 2164-2167
67. Ong, W.; Comez-Kaifer, M.; Kaifer, A. E. Org. Lett. 2002, 4, 1791-1794
68. Thordarson, P. Chem. Soc. Rev. 2011, 40, 1305-1323
69. Connors, K. A. Binding Constants; Wiley: New York, 1987; Chapter 4.
70. Kaifer, A. E.; Li, W.; Yi, S. Isr. J. Chem. 2011, 51, 496-505
71. Ong, W.; Kaifer, A. E. J. Org. Chem. 2004, 69, 1383-1385
72. Tang, H.; Fuentealba, D.; Ko, Y. H.; Narayanan, S.; Kim, K.; Bohne, C. J. Am. Chem. Soc. 2011, 133, 20623-20633
73. Barigelletti, F.; Belser, P.; von Zelewsky, A.; Juris, A.; Balzani, V. J. Phys. Chem. 1985, 89, 3680-3684
74. Bhasikuttan, A. C.; Mohanty, J.; Nau, W. M.; Pal, H. Angew. Chem., Int. Ed. 2007, 46, 4120-4122
75. Mortimer, R. J.; Reynolds, J. R. Displays 2008, 29, 424-431