Self-assembly of oligo(para-phenylenevinylene)s through arene-perfluoroarene interactions: π gels with longitudinally controlled fiber growth and supramolecular exciplex-mediated enhanced emission

Chemistry - A European Journal

Volumn 14, Issue 31, 2008, Pages 9577-9584

  Babu, Sukumaran S ^a   Praveen, Vakayil K ^a   Prasanthkumar, Seelam ^a   Ajayaghosh, Ayyappanpillai ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

Exciplex; Fluorine; Organogel; Pi stacking; Self assembly

Indexed keywords

AMINES; ARGON; COAGULATION; COLLOIDS; FIBERS; FLOW INTERACTIONS; FLUORESCENCE; FLUORINE; GELATION; GELS; HYDROGEN; HYDROGEN BONDS; LIGHT EMISSION; LUMINESCENCE; ORGANIC COMPOUNDS; QUENCHING; SUPRAMOLECULAR CHEMISTRY;

AROMATIC AMINES; EMISSION INTENSITIES; ENHANCED EMISSIONS; EXCIPLEX; FIBER GROWTHS; FLUORESCENCE QUENCHING; FUNCTIONALIZED; GEL STATES; HIERARCHICAL; HYDROGEN BONDINGS; LONGITUDINAL FIBERS; ORGANOGEL; PENTAFLUOROPHENYL; PHENYLENEVINYLENE; PI-STACKING; STACKING; SUPRAMOLECULAR;

SELF ASSEMBLY;

EID: 55049104277     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801255     Document Type: Article

References (92)

1. a) F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491-1546;
2. b) for a review of supramolecular dye chemistry, see: C.-C. You, R. Dobrawa, C. R. Saha-Möller, F. Würthner, Top. Curr. Chem. 2005, 258, 39-82;
3. c) A. Ajayaghosh, S. J. George, A. P. H. J. Schenning, Top. Curr. Chem. 2005, 258, 83-118.
4. a) A. Ajayaghosh, V. K. Praveen, Acc. Chem. Res. 2007, 40, 644-656;
5. b) A. Ajayaghosh, V. K. Praveen, S. Srinivasan, R. Varghese, Adv. Mater. 2007, 19, 411-415;
6. c) J. van Herrikhuyzen, S. J. George, M. R. J. Vos, N. A. J. M. Sommerdijk, A. Ajayaghosh, S. C. J. Meskers, A. P. H. J. Schenning, Angew. Chem. 2007, 119, 1857-1860;
7. Angew. Chem. Int. Ed. 2007, 46, 1825-1828;
8. d) A. Ajayaghosh, C. Vijayakumar, R. Varghese, S. J. George, Angew. Chem. 2006, 118, 470-474;
9. Angew. Chem. Int. Ed. 2006, 45, 456-460;
10. e) V. K. Praveen, S. J. George, A. Ajayaghosh, Macromol. Symp. 2006, 241, 1-8;
11. f) R. Varghese, S. J. George, A. Ajayaghosh, Chem. Commun. 2005, 593-595;
12. g) S. J. George, A. Ajayaghosh, Chem. Eur. J. 2005, 11, 3217-3227;
13. h) A. Ajayaghosh, S. J. George, J. Am. Chem. Soc. 2001, 123, 5148-5149.
14. a) A. Ajayaghosh, V, K. Praveen, C. Vijayakumar, Chem. Soc. Rev. 2008, 37, 109-122;
15. b) A. Ajayaghosh, V. K. Praveen, C. Vijayakumar, S. J. George, Angew. Chem. 2007, 119, 6376-6381;
16. Angew. Chem. Int. Ed. 2007, 46, 6260-6265;
17. c) V. K. Praveen, S. J. George, R. Varghese, C. Vijayakumar, A. Ajayaghosh, J. Am. Chem. Soc. 2006, 128, 7542-7550;
18. d) A. Ajayaghosh, C. Vijayakumar, V. K. Praveen, S. S. Babu, R. Varghese, J. Am. Chem. Soc. 2006, 128, 7174-7175;
19. e) A. Ajayaghosh, S. J. George, V. K. Praveen, Angew. Chem. 2003, 115, 346-349;
20. Angew. Chem. Int. Ed. 2003, 42, 332-335.
21. a) K. Reichenbächer, H. I. Süss, J. Hulliger, Chem. Soc. Rev. 2005, 34, 22-30;
22. b) M. Pagliaro, R. J. Ciriminna, J.. Mater. Chem. 2005, 15, 4981-4991;
23. c) S. Lorenzo, G. R. Lewis, I. Dance, New J. Chem. 2000, 24, 295-304;
24. d) C. R. Patrick, G. S. Prosser, Nature 1960, 187, 1021-1021.
25. a) Z. Wang, F. Dötz, V. Enkelmann, K. Müllen, Angew. Chem. 2005, 117, 1273-1276;
26. Angew. Chem. Int. Ed. 2005, 44, 1247-1250;
27. b) F. Ponzini, R. Zagha, K. Hardcastle, J. S. Siegel, Angew. Chem. 2000, 112, 2413-2415;
28. Angew. Chem. Int Ed. 2000, 39, 2323-2325;
29. c) S. Wang, G. C. Bazan, Chem. Phys. Lett. 2001, 333, 437-443;
30. d) G. P. Bartholomew, X. Bu, G. C. Bazan, Chem. Mater. 2000, 12, 2311-2318;
31. e) M. L Renak, G. P. Bartholomew, S. Wang, P. J. Ricatto, R. J. Lachicotte, G. C. Bazan, J. Am. Chem. Soc. 1999, 121, 7787-7799;
32. f) B. Strehmel, A. M. Sarker, J. H. Malpert, V. Strehmel, H. Seifert, D. C. Neckers, J. Am. Chem. Soc. 1999, 121, 1226-1236.
33. a) S. W. Watt, C. Dai, A. J. Scott, J. M. Burke, R. L. Thomas, J. C. Collings, C. Viney, W. Clegg, T. B. Marder, Angew. Chem. 2004, 116, 3123-3125;
34. Angew. Chem. Int. Ed. 2004, 43, 3061-3063;
35. b) C. E. Smith, P. S. Smith, R. L. Thomas, E. G. Robins, J. C. Collings, C. Dai, A. J. Scott, S. Borwick, A. S. Batsanov, S. W. Watt, S. J. Clark, C. Viney, J. A. K. Howard, W. Clegg, T. B. Marder, J. Mater. Chem. 2004, 14, 413-420;
36. c) C. Dai, P. Nguyen, T. B. Marder, A. J. Scott, W. Clegg, C. Viney, Chem. Commun. 1999, 2493-2494.
37. a) R. Capelli, M. A. Loi, C. Taliani, H. B. Hansen, M. Murgia, G. Ruani, M. Muccini, P. W. Lovenich, W. J. Feast, Synth. Met. 2003, 139, 909-912;
38. b) W. J. Feast, P. W. Lövenich, H. Puschmann, C. Taliani, Chem. Commun. 2001, 505-506.
39. a) A. F. M. Kilbinger, R. H. Grubbs, Angew. Chem. 2002, 114, 1633-1636;
40. Angew. Chem. Int. Ed. 2002, 41, 1563-1566;
41. b) M. Weck, A. R. Dunn, K. Matsumoto, G. W. Coates, E. B. Lobkovsky, R. H. Grubbs, Angew. Chem. 1999, 111, 2909-2912;
42. Angew. Chem. Int. Ed. 1999, 38, 2741-2745;
43. c) G. W. Coates, A. R. Dunn, L. M. Henling, J. W. Ziller, E. B. Lobkovsky, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 3641-3649;
44. d) G. W. Coates, A. R. Dunn, L. M. Henling, D. A. Dougherty, R. H. Grubbs, Angew. Chem. 1997, 109, 290-293;
45. Angew. Chem. Int. Ed. Engl. 1997, 36, 248-251.
46. F. Babudri, G. M. Farinola, F. Naso, R. Ragni, Chem. Commun. 2007, 1003-1022.
47. a) A. Hori, A. Akasaka, K. Biradha, S. Sakamoto, K. Yamaguchi, M. Fujita, Angew. Chem. 2002, 114, 3403-3406;
48. Angew. Chem. Int. Ed. 2002, 41, 3269-3272;
49. b) M. J. Marsella, Z.-Q. Wang, R. J. Reid, K. Yoon, Org. Lett. 2001, 3, 885-887.
50. a) Molecular Gels, Materials with Self-Assembled Fibrillar Networks (Eds.: P. Terech, R. G. Weiss), Kluwer Press, Dordrecht, The Netherlands, 2005;
51. b) T. Ishi-i, S. Shinkai, Top. Curr. Chem. 2005, 258, 119-160;
52. c) R Luboradzki, O. Gronwald, A. Ikeda, S. Shinkai, Chem. Lett. 2000, 1148;
53. d) J. H. van Esch, B. L. Feringa, Angew. Chem. 2000, 112, 2351-2354;
54. Angew. Chem. Int. Ed. 2000, 39, 2263-2266.
55. a) N.J. Turro, Modern Molecular Photochemistry, Benjamin-Cummings, Menlo Park, California, 1978, p. 135;
56. b) A. Weller in The Exciplex (Eds.: M. Gordon, W. Ware), Academic Press, New York, 1975, pp. 23-28.
57. a) S. A. Jenekhe, Adv. Mater. 1995, 7, 309-311;
58. b) S. A. Jenekhe, J. A. Osaheni, Science 1994, 265, 765-768;
59. c) J. A. Osaheni, S. A. Jenekhe, Macromolecules 1994, 27, 739-742;
60. d) J. A. Osaheni, S. A. Jenekhe, Macromolecules 1993, 26, 4126-4128.
61. a) J. Kalinowski, M. Cocchi, D. Virgili, V. Fattori, J. A. G. Williams, Adv. Mater. 2007, 19, 4000-4007;
62. b) C. Yin, T, Kietzke, D. Neher, H.-H. Hörhold, Appl. Phys. Lett. 2007, 90, 092117;
63. c) A. C. Morteani, A. S. Dhoot, J. S. Kim, C. Silva, N. C. Greenham, C. Murphy, E. Moons, S. Cina, R. H. Friend, Adv. Mater. 2003, 15, 1708-1712;
64. d) H. Meier, Angew. Chem. 2001, 113, 1903-190;
65. Angew. Chem. Int. Ed. 2001, 40, 1851-1853;
66. e) J.-F. Wang, Y. Kawabe, S. E. Shaheen, M. M. Morrell, G. E. Jabbour, P. A. Lee, J. Anderson, N. R. Armstrong, B. Kippelen, E. A. Mash, N. Peyghambarian, Adv. Mater. 1998, 10, 230-233.
67. a) D. W. Cho, M. Fujitsuka, K. H. Choi, M. J. Park, U. C. Yoon, T. Majima, J. Phys. Chem. B 2006, 110, 4576-4582;
68. b) T. Offermans, P. A. van Hal, S, C. J. Meskers, M. M. Koetse, R. A. J. Janssen, Phys. Rev. B 2005, 72, 045213, 1-11.
69. a) X. Yang, R. Lu, T. Xu, P. Xue, X. Liu Y. Zhao, Chem. Commun. 2008, 453-455;
70. b) P. Xue, R. Lu, O. Chen, Y. Zhang, H. Nomoto, M. Takafuji, H. Ihara, Chem. Eur. J. 2007, 13, 8231-8239;
71. c) N. S. S. Kumar, S. Varghese, O. Narayan, S. Das, Angew. Chem. 2006, 118 6465-6469;
72. Angew. Chem. Int. Ed. 2006, 45, 6317-6321;
73. d) J. F. Hulvat, M. Sofos, K. Tajima, S. I. Stupp, J. Am. Chem. Soc. 2005, 127, 366-372;
74. e) B.-K. An, D.-S. Lee, J.-S. Lee, Y.-S, Park, H.-S. Song, S. Y. Park, J. Am. Chem. Soc. 2004, 126, 10232-10233;
75. f) S. Y. Ryu, S. Kim, J. Seo, Y.-W. Kim, O.-H. Kwon, D.-J. Jang, S. Y. Park, Chem. Commun. 2004, 70-71;
76. g) H. Iharaa, T. Yamadaa, M. Nishiharaa, T. Sakuraia, M. Takafujia, H. Hachisakob, T. Sagawa, J. Mol. Liq. 2004, 111, 73-76;
77. h) B.-K. An, S.-K. Kwon, S.-D. Jung, S. Y. Park, J. Am. Chem. Soc. 2002, 124, 14410-14415;
78. i) R. Deans, J. Kim, M. R. Machacek, T. M. Swager, J. Am. Chem. Soc. 2000, 122, 8565-8566.
79. B. Wang, M. R. Wasielewski, J. Am. Chem. Soc. 1997, 119, 12-21.
80. a) J. R. Lakowicz, Principles of Fluorescence Spectroscopy, 2nd ed., Kluwer Academic/Plenum Publishers, New York, 1999;
81. b) O. Weber, F. W. J. Teale, Trans. Faraday Soc. 1957, 53, 646-655;
82. c) S. A. Jonker, F. Ariese, J. W. Verhoeven, Recl. Trav. Chim. Pays-Bas. 1989, 108, 109-115.
83. Y. Kim, T. M. Swager, Chem. Commun. 2005, 372-374.
84. a) R. Laatikainen, J. Ratilainen, R. Sebastian, H. Santa, J. Am. Chem. Soc. 1995, 117, 11006-11010;
85. b) F. Cozzi, F. Ponzini, R. Annunziata, M. Cinquini, J. S. Siegel, Angew. Chem. 1995, 107, 1092-1094;
86. Angew. Chem. Int. Ed. Engl. 1995, 34, 1019-1021;
87. c) R. Laatikainen, H. Santa, Y, Hiltunen, J. Lounila, J. Magn. Reson. 1993, A104, 238-241.
88. D.G. Naae, Acta Crystallogr. Sect. B: Struct. Sci. 1979, 35, 2765-2768.
89. a) R. Huenerbein, S. Grimme, Chem. Phys. 2008, 343, 362-371;
90. b) R. Ide, Y. Shikata, S. Misumi, T. Ikada, N. Malaga, J. Chem. Soc. Chem. Commun. 1972, 1009.
91. a) L.-O. Pålsson, A. P. Monkman, Adv. Mater. 2002, 14, 757-758;
92. b) J. C. de Mello, H. F. Wittmann, R. H. Friend, Adv. Mater. 1997, 9, 230-232.