Functional organogel based on a hydroxyl naphthanilide derivative and aggregation induced enhanced fluorescence emission

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 217, Issue 1, 2011, Pages 40-48

  Nayak, Manoj Kumar ^a  

^a TEXAS A AND M UNIVERSITY AT QATAR   (Qatar)

Author keywords

Excited state intramolecular proton transfer (ESIPT); Gelation induced enhanced fluorescence emission (GIEFE); J aggregation; Naphthanilide self assembly; Twisted intramolecular charge transfer (TICT)

Indexed keywords

EID: 78650679552     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2010.09.014     Document Type: Article

References (93)

1. P. Terech, and R.G. Weiss Chem. Rev. 97 1997 3133 3159
2. J.H. van Esch, and B.L. Feringa Angew. Chem. Int. Ed. 39 2000 2263 2266
3. L.A. Estorff, and A.D. Hamilton Chem. Rev. 104 2004 1201 1217
4. T. Ishi-I, and S. Shinkai Top. Curr. Chem. 258 2005 119 160
5. F. Camerel, L. Bonardi, M. Schmutz, and R. Ziessel J. Am. Chem. Soc. 128 2006 4548 4549
6. A. Brizard, R. Oda, and I. Huc Top. Curr. Chem. 256 2005 167 218
7. A. Ajayaghosh, and V.K. Praveen Acc. Chem. Res. 40 2007 644 656
8. C. Wang, D. Zhang, and D. Zhu Langmuir 23 2007 1478 1482
9. S. Das, S. Varghese, and N.S.S. Kumar Langmuir 26 2010 1598 1609
10. C. Wang, Q. Chen, F. Sun, D. Zhang, G. Zhang, Y. Huang, R. Zhao, and D. Zhu J. Am. Chem. Soc. 132 2010 3092 3096
11. H. Komatsu, S. Matsumoto, S.-I. Tamaru, K. Kaneko, M. Ikeda, and I. Hamachi J. Am. Chem. Soc. 131 2009 5580 5585
12. X. Chen, Z. Huang, S.-Y. Chen, K. Li, X.-Q. Yu, and L. Pu J. Am. Chem. Soc. 132 2010 7297 7299
13. M.-O.M. Piepenbrock, G.O. Lloyd, N. Clarke, and J.W. Steed Chem. Rev. 110 2010 1960 2004
14. F. Fages Angew. Chem. Int. Ed. 45 2006 1680 1682
15. A.R. Hirst, B. Escuder, J.F. Miravet, and D.K. Smith Angew. Chem. Int. Ed. 47 2008 8002 8018
16. N.M. Sangeetha, and U. Maitra Chem. Soc. Rev. 34 2005 821 836
17. H. Dai, Q. Chen, H. Qin, Y. Guan, D. Shen, Y. Hua, Y. Tang, and J. Xu Macromolecules 39 2006 6584 6589
18. R.M.K. Ramanan, P. Chellamuthu, L. Tang, and K.T. Nguyen Biotechnol. Prog. 22 2006 118 125
19. J.W. Chung, B.-K. An, and S.Y. Park Chem. Mater. 20 2008 6750 6755
20. X. Tong, Y. Zhao, B.-K. An, and S.Y. Park Adv. Funct. Mater. 16 2006 1799 1804
21. A. Kishimura, T. Yamashita, and T. Aida J. Am. Chem. Soc. 127 2005 179 183
22. M. Carrasco-Orozco, W.C. Tsoi, M. O'Neill, M.P. Aldred, P. Vlachos, and S.M. Kelly Adv. Mater. 18 2006 1754 1758
23. F. Camerel, R. Ziessel, B. Donnio, C. Bourgogne, D. Guillon, M. Schmutz, C. Iacovita, and J.-P. Bucher Angew. Chem. Int. Ed. 46 2007 2659 2662
24. H. Yang, T. Yi, Z. Zhou, Y. Zhou, J. Wu, M. Xu, F. Li, and C. Huang Langmuir 23 2007 8224 8230
25. Q. Liu, Y. Wang, W. Li, and L. Wu Langmuir 23 2007 8217 8223
26. T.H. Kim, D.G. Kim, M. Lee, and T.S. Lee Tetrahedron 66 2010 1667 1672
27. P. Mukhopadhyay, Y. Iwashita, M. Shirakawa, S.-I. Kawano, N. Fujita, and S. Shinkai Angew. Chem. Int. Ed. 45 2006 1592 1595
28. A. Ghoussoub, and J.-M. Lehn Chem. Commun. 2005 5763 5765
29. Z. Dzolic, A.D. Cametti, A.D. Cort, L. Mandolini, and M. Zinic Chem. Commun. 2007 3535 3537
30. S. Wang, W. Shen, Y. Feng, and H. Tian Chem. Commun. 2006 1497 1499
31. M. Shirakawa, N. Fujita, T. Tani, K. Kaneko, M. Ojima, A. Fujii, M. Ozaki, and S. Shinkai Chem. Eur. J. 13 2007 4155 4162
32. K. Sugiyasu, N. Fujita, and S. Shinkai J. Mater. Chem. 15 2005 2747 2754
33. J. Puigmart-Luis, V. Laukhin, Á. Pérez del Pino, J. Vidal-Gancedo, C. Rovira, E. Laukhina, and D.B. Amabilino Angew. Chem. Int. Ed. 46 2007 238 241
34. L. Schmidt-Mende, A. Fechtenkotter, E. Moons, R.H. Friend, and J.D. Mack-Enzie Science 293 2001 1119 1122
35. Z. Huo, S. Dai, C. Zhang, F. Kong, X. Fang, L. Guo, W. Liu, L. Hu, X. Pan, and K. Wang J. Phys. Chem. B 112 2008 12927 12933
36. K. Sugiyasu, S.-i. Kawano, N. Fujita, and S. Shinkai Chem. Mater. 20 2008 2863 2865
37. V.K. Praveen, S.J. George, R. Varghese, C. Vijayakumar, and A. Ajayaghosh J. Am. Chem. Soc. 128 2006 7542 7550
38. J.H. Jung, S.J. Lee, J.A. Rim, H. Lee, T.-S. Bae, S.S. Lee, and S. Shinkai Chem. Mater. 17 2005 459 462
39. A. Ajayghosh, V.K. Praveen, and C. Vijayakumar Chem. Soc. Rev. 37 2008 109 122
40. K. Sugiyasu, N. Fujita, and S. Shinkai Angew. Chem. Int. Ed. 43 2004 1229 1233
41. T. Nakashima, and N. Kimizuka Adv. Mater. 14 2004 1113 1116
42. X. Zhang, L. Guo, F.-Y. Wu, and Y.-B. Jiang Org. Lett. 5 2003 2667 2670
43. H. Mishra J. Phys. Chem. B 110 2006 9387 9396
44. L. Zhao, C. YaoHan, and J. YunBao Sci. China Ser. B: Chem. 52 2009 786 792
45. S.K. Dubey, A.K. Singh, H. Singh, S. Sharma, R.N. Iyer, J.C. Katiyar, P. Goel, and A.B. Sen J. Med. Chem. 21 1978 1178 1181
46. H. Singh, S. Sharma, R.N. Iyer, J.C. Katiyar, and A.B. Sen Z. Naturforsch. C 33 1978 447 448
47. K.C. Tsou, and S. Matsukawa J. Med. Chem. 11 1968 1097 1099
48. M.K. Nayak, J. Seo, S. Park, and S.Y. Park J. Photochem. Photobiol. A: Chem. 191 2007 228 232
49. I.B. Berlman Handbook of Fluorescence Spectra of Aromatic Molecules 1971 Academic Press New York
50. J.C. de Mello, H.F. Wittmann, and R.H. Friend Adv. Mater. 9 1997 230 232
51. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
52. J. Llano, J. Raber, and L.A. Eriksson J. Photochem. Photobiol. A: Chem. 154 2003 235 243
53. R. Bauernschmitt, R. Ahlrichs, F.H. Hennrich, and M.M. Kappes J. Am. Chem. Soc. 120 1998 5052 5059
54. M.E. Casida J. Chem. Phys. 108 1998 4439 4449
55. R.E. Stratmann, G.E. Scuseria, and M.J. Frisch J. Chem. Phys. 109 1998 8218 8224
56. J. Llano, and L.A. Eriksson Phys. Chem. Chem. Phys. 6 2004 4707 4713
57. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, revision B.03 2003 Gaussian Inc. Pittsburgh, PA
58. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart J. Am. Chem. Soc. 107 1985 3902 3909
59. G.B. Rocha, R.O. Freire, A.M. Simas, and J.J.P. Stewart J. Comput. Chem. 27 2006 1101 1111
60. G. Rauhut, T. Clark, and T. Steinke J. Am. Chem. Soc. 115 1993 9174 9181
61. H. Mishra, S. Maheshwary, H.B. Tripathi, and N. Sathyamurthy J. Phys. Chem. A 109 2005 2746 2754
62. R. Misra, A. Mandal, M. Mukhopadhyay, D.K. Maity, and S.P. Bhattacharyya J. Phys. Chem. B 113 2009 10779 10791
63. S. Mitra, R. Das, S.P. Bhattacharyya, and S. Mukherjee J. Phys. Chem. A 101 1997 293 298
64. M.K. Nayak, and S.K. Dogra J. Photochem. Photobiol. A: Chem. 169 2005 79 88
65. M.K. Nayak, and S.K. Dogra J. Photochem. Photobiol. A: Chem. 161 2004 169 183
66. M.K. Nayak, and S.K. Dogra Spectrochim. Acta A 61 2005 1247 1257
67. J.D. Jong, J.D.L.N.R. Lucas, M. Kellog, J.H. van Esch, and B.L. Feringa Science 304 2004 278 281
68. S.K. Samanta, A. Pal, and S. Bhattacharya Langmuir 25 2009 8567 8578
69. H. Basit, A. Pal, S. Sen, and S. Bhattacharya Chem. Eur. J. 14 2008 6534 6545
70. A. Pal, Y.K. Ghosh, and S. Bhattacharya Tetrahedron 63 2007 7334 7348
71. T. Kar, S. Debnath, D. Das, A. Shome, and P.K. Das Langmuir 25 2009 8639 8648
72. G. Palui, and A. Banerjee J. Phys. Chem. B 112 2008 10107 10115
73. J. Peng, K. Liu, X. Liu, H. Xia, J. Liu, and Y. Fang New J. Chem. 32 2008 2218 2224
74. M. Teng, G. Kuang, X. Jia, M. Gao, Y. Li, and Y. Wei J. Mater. Chem. 19 2009 5648 5654
75. M.K. Nayak, B.-H. Kim, J.E. Kwon, S. Park, J. Seo, J.W. Chung, and S.Y. Park Chem. Eur. J. 16 2010 7437 7447
76. J. Seo, J.W. Chung, E.-H. Jo, and S.Y. Park Chem. Commun. 2008 2794 2796
77. J. Luo, Z. Xie, J.W.Y. Lam, L. Cheng, H. Chen, C. Qiu, H.S. Kwok, X. Zhan, Y. Liu, D. Zhu, and B. Tang Chem. Commun. 2001 1740 1741
78. P. Chen, R. Lu, P. Xue, T. Xu, G. Chen, and Y. Zhao Langmuir 25 2009 8395 8399
79. P. Xue, R. Lu, G. Chen, Y. Zhang, H. Nomoto, M. Takafuji, and H. Ihara Chem. Eur. J. 13 2007 8231 8239
80. Y. Chen, Y. Lv, Y. Han, B. Zhu, F. Zhang, Z. Bo, and C.-Y. Liu Langmuir 25 2009 8548 8555
81. S. Kim, Q. Zheng, G.S. He, D.J. Bharali, H.E. Pudavar, A. Baev, and P.N. Prasad Adv. Funct. Mater. 16 2006 2317 2323
82. S. Abraham, R.K. Vijayaraghavan, and S. Das Langmuir 25 2009 8507 8513
83. B. An, S. Kwon, S. Jung, and S.Y. Park J. Am. Chem. Soc. 124 2002 14410 14415
84. C. Wang, D. Zhang, J. Xiang, and D. Zhu Langmuir 23 2007 9195 9200
85. C.Y. Bao, R. Lu, M. Jin, P.C. Xue, C.H. Tan, G.F. Liu, and Y.Y. Zhao Org. Biomol. Chem. 3 2005 2508 2512
86. S. Bhattacharya, and S.K. Samanta Langmuir 25 2009 8378 8381
87. F.D. Lewis, and W. Liu J. Phys. Chem. A 106 2002 1976 1984
88. S. Varghese, N.S.S. Kumar, A. Krishna, D.S.S. Rao, S.K. Prasad, and S. Das Adv. Funct. Mater. 19 2009 2064 2073
89. A. Chowdhury, S. Wachsmann-Hogiu, P.R. Bangal, I. Raheem, and L.A. Peteanu J. Phys. Chem. B 105 2001 12196 12201
90. V.C. Vargas J. Phys. Chem. A 108 2004 281 288
91. F. Robert, A.D. Naik, B. Tinant, R. Robiette, and Y. Garcia Chem. Eur. J. 15 2009 4327 4342
92. F. Camerel, L. Bonardi, G. Ulrich, L. Charbonniere, B. Donnio, C. Bourgogne, D. Guillon, P. Retailleau, and R. Ziessel Chem. Mater. 18 2006 5009 5021
93. A.N. Shipway, E. Katz, and I. Willner ChemPhysChem 1 2000 18 52