Intermolecular hydrogen-bonding effects on photophysics and photochemistry

International Reviews in Physical Chemistry

Volumn 32, Issue 4, 2013, Pages 589-609

  Song, Peng ^a   Ma, Feng Cai ^a  

^a LIAONING UNIVERSITY   (China)

Author keywords

dihydrogen bond; excited state double proton transfer; fluorescence quenching; fluorescent probes; intermolecular hydrogen bonding; photophysics and photochemistry; sensing mechanism; spectral shifts

Indexed keywords

EID: 84885425088     PISSN: 0144235X     EISSN: 1366591X     Source Type: Journal    
DOI: 10.1080/0144235X.2013.811891     Document Type: Review

References (161)

1. Han, K.L. and Zhao, G.J. 2010. Hydrogen Bonding and Transfer in the Excited State, ISBN: 978-0-470-66677-7, Chichester: John Wiley & Sons.
2. Agmon, N. 2012. Acc. Chem. Res., 45: 63
3. Wang, D.D. and Zhao, G.J. 2013. Commun. Comput. Chem., 1: 181
4. Del Bene, J.E., Alkorta, I. and Elguero, J. 2011. Phys. Chem. Chem. Phys., 13: 13951
5. Hujo, W. and Grimme, S. 2011. Phys. Chem. Chem. Phys., 13: 13942
6. Tanner, C., Manca, C. and Leutwyler, S. 2003. Science, 302: 1736
7. Miller, B.J., Lane, J.R. and Kjaergaard, H.G. 2011. Phys. Chem. Chem. Phys., 13: 14183
8. Kina, D., Nakayama, A., Noro, T., Taketsugu, T. and Gordon, M.S. 2008. J. Phys. Chem. A, 112: 9675
9. Liu, X.C. and Xu, Y.J. 2011. Phys. Chem. Chem. Phys., 13: 14235
10. Liu, J., Shepperson, B., Ellis, A.M. and Yang, S. 2011. Phys. Chem. Chem. Phys., 13: 13920
11. Kolesov, B.A., Mikhailenko, M.A. and Boldyreva, E.V. 2011. Phys. Chem. Chem. Phys., 13: 14243
12. Schmies, M., Patzer, A., Fujii, M. and Dopfer, O. 2011. Phys. Chem. Chem. Phys., 13: 13926
13. Kim, K.S., Oh, K.S. and Lee, J.Y. 2000. Proc. Natl. Acad. Sci. USA, 97: 6373
14. Kozmon, S., Matuška, R., Spiwok, V. and Koča, J. 2011. Phys. Chem. Chem. Phys., 13: 14215
15. Zhang, L.B. and Bu, Y.-X. 2008. J. Phys. Chem. B, 112: 10723
16. Li, G.Y., Li, Y.H., Zhang, H. and Cui, G.H. 2013. Commun. Comput. Chem., 1: 88
17. Ma, X.N., Yan, L.Y., Wang, X.F., Guo, Q.J. and Xia, A.D. 2011. J. Phys. Chem. A, 115: 7937
18. Ma, X.N., Yan, L.Y., Wang, X.F., Guo, Q.J. and Xia, A.D. 2011. Phys. Chem. Chem. Phys., 13: 17273
19. Wang, H., Su, H.M., Qian, H.L., Wang, Z.H., Wang, X.F. and Xia, A.D. 2010. J. Phys. Chem. A, 114: 9130
20. Sun, L.C., Burkitt, M., Tamm, M., Raymond, M.K., Abrahamsson, M., LeGourrierec, D., Frapart, Y., Magnuson, A., Kenez, P.H., Brandt, P., Tran, A., Hammarstrom, L., Styring, S. and Akermark, B. 1999. J. Am. Chem. Soc., 121: 6834
21. Duan, L.L., Fischer, A., Xu, Y.H. and Sun, L.C. 2009. J. Am. Chem. Soc., 131: 10397
22. Kim, T.G. and Topp, M.R. 2004. J. Phys. Chem. A, 108: 7653
23. Chen, Y., Palmer, P.M. and Topp, M.R. 2002. Int. J. Mass Spec., 220: 231
24. Barbatti, M. and Lischka, H. 2008. J. Am. Chem. Soc., 130: 6831
25. Hughes, J.M., Hutter, M.C., Reimers, J.R. and Hush, N.S. 2001. J. Am. Chem. Soc., 123: 8550
26. Niu, Y.L., Peng, Q., Deng, C.M., Gao, X. and Shuai, Z.G. 2010. J. Phys. Chem. A, 114: 7817
27. Fujii, A., Hayashi, H., Park, J.W., Kazama, T., Mikami, N. and Tsuzuki, S. 2011. Phys. Chem. Chem. Phys., 13: 14131
28. Dong, H., Hua, W.J. and Li, S.H. 2007. J. Phys. Chem. A, 111: 2941
29. Herrebout, W.A. and Suhm, M.A. 2011. Phys. Chem. Chem. Phys., 13: 13858
30. Kollipost, F., Hesse, S., Lee, J.J. and Suhm, M.A. 2011. Phys. Chem. Chem. Phys., 13: 14176
31. Wan, Y., Yan, L., Zhao, Z., Ma, X., Guo, Q., Jia, M., Lu, P., Ramos Ortiz, G., Maldonado, J.L., Rodríguez, M. and Xia, A.D. 2010. J. Phys. Chem. B, 114: 11737
32. Jia, M., Ma, X., Yan, L., Wang, H., Guo, Q., Wang, X., Wang, Y., Zhan, X. and Xia, A.D. 2010. J. Phys. Chem. A, 114: 7345
33. Aulimer, D., Wang, S., Chen, X. and Xia, A.D. 2009. J. Am. Chem. Soc., 131: 5742
34. Alkorta, I., Soteras, I. and Del Bene, J.E. 2011. Phys. Chem. Chem. Phys., 13: 14026
35. Bhattacharyya, K. 2003. Acc. Chem. Res., 36: 95
36. Yang, F., Yu, L.J., Wang, P., Ai, X.C., Wang, Z.Y. and Zhang, J.P. 2011. J. Phys. Chem. B, 115: 7906
37. Chen, X.B., Gao, L.H., Fang, W.H. and Phillips, D.L. 2010. J. Phys. Chem. B, 114: 5206
38. Fang, W.H. 2008. Acc. Chem. Res., 41: 452
39. Nie, B.N., Stutzman, J. and Xie, A.H. 2005. Biophys. J., 88: 2833
40. Yu, F., Li, P., Li, G., Zhao, G., Chu, T. and Han, K. 2011. J. Am. Chem. Soc., 133: 11030
41. Jiang, N. and Ma, J. 2009. Phys. Chem. Chem. Phys., 11: 5100
42. Feng, G., Evangelisti, L., Favero, L.B., Grabow, J.U., Xia, Z.N. and Caminati, W. 2011. Phys. Chem. Chem. Phys., 13: 14092
43. Weng, Y.X., Li, L., Liu, Y., Wang, L. and Yang, G.Z. 2003. J. Phys. Chem. B, 107: 4356
44. Baglole, K.N., Boland, P.G. and Wagner, B.D. 2005. J. Photochem. Photobiol., A, 173: 230
45. Seurre, N., Barbu-Debus, K.L., Lahmani, F., Zehnacker-Rentien, A. and Sepiol, J. 2003. Chem. Phys., 295: 21
46. Seurre, N., Sepiol, J., Lahmani, F., Zehnacker-Rentien, A. and Barbu-Debus, K.L. 2004. Phys. Chem. Chem. Phys., 6: 4658
47. Ghosh, H.N., Adamczyk, K., Verma, S., Dreyer, J. and Nibbering, E.T.J. 2012. Chem. Eur. J., 18: 4930
48. Han, F., Chi, L., Wu, W.T., Liang, X.F., Fu, M.Y. and Zhao, J.Z. 2008. J. Photochem. Photobiol., A, 196: 10
49. Zhao, J.Z., Ji, S.M., Chen, Y.H., Guo, H.M. and Yang, P. 2012. Phys. Chem. Chem. Phys., 14: 8803
50. Zhao, Y.P., Zhao, C.C., Wu, L.Z., Zhang, L.P., Tung, C.H. and Pan, Y.J. 2006. J. Org. Chem., 71: 2143
51. Tung, C.H., Wu, L.Z., Zhang, L.P. and Chen, B. 2003. Acc. Chem. Res., 36: 39
52. Sobolewski, A.L. and Domcke, W. 2006. Phys. Chem. Chem. Phys., 8: 3410
53. Sobolewski, A.L. and Domcke, W. 2004. J. Phys. Chem. A, 108: 10917
54. Sobolewski, A.L., Domcke, W., Dedonder-Lardeux, C. and Jouvet, C. 2002. Phys. Chem. Chem. Phys., 4: 1093
55. Lan, Z.G., Frutos, L.M., Sobolewski, A.L. and Domcke, W. 2008. Proc. Natl. Acad. Sci. USA, 105: 12707
56. Shemesh, D., Sobolewski, A.L. and Domcke, W. 2010. Phys. Chem. Chem. Phys., 12: 4899
57. Shemesh, D. and Domcke, W. 2011. Chem. Phys. Chem., 12: 1833
58. Zhao, G.J. and Han, K.L. 2012. Acc. Chem. Res., 45: 404
59. Zhao, G.J. and Han, K.L. 2007. J. Phys. Chem. A, 111: 2469
60. Zhao, G.J. and Han, K.L. 2008. Chem. Phys. Chem., 9: 1842
61. Zhao, G.J. and Han, K.L. 2007. J. Phys. Chem. A, 111: 9218
62. Zhao, G.J. and Han, K.L. 2009. J. Phys. Chem. A, 113: 14329
63. Zhao, G.J., Liu, J.Y., Zhou, L.C. and Han, K.L. 2007. J. Phys. Chem. B, 111: 8940
64. Zhao, G.J. and Han, K.L. 2008. Biophys. J., 94: 38
65. Zhao, G.J. and Han, K.L. 2008. J. Comput. Chem., 29: 2010
66. Zhao, G.J., Han, K.L. and Stang, P.J. 2009. J. Chem. Theory Comput., 5: 1955
67. Zhao, G.J., Northrop, B.H., Han, K.L. and Stang, P.J. 2010. J. Phys. Chem. A, 114: 9007
68. Zeng, J., Hush, N.S. and Reimers, J.R. 1993. J. Chem. Phys., 99: 1496
69. Zeng, J., Hush, N.S. and Reimers, J.R. 1993. J. Chem. Phys., 99: 1508
70. Zeng, J., Woywod, J.C., Hush, N.S. and Reimers, J.R. 1995. J. Am. Chem. Soc., 117: 8618
71. Zeng, J., Hush, N.S. and Reimers, J.R. 1996. J. Phys. Chem., 100: 9561
72. Cai, Z.L. and Reimers, J.R. 2002. J. Phys. Chem. A, 106: 8769
73. Fischer, G., Cai, Z.L., Reimers, J.R. and Wormell, P. 2003. J. Phys. Chem. A, 107: 3093
74. Cai, Z.L. and Reimers, J.R. 2007. J. Phys. Chem. A, 111: 954
75. Sun, M.T. 2006. J. Chem. Phys., 124: 054903
76. Ahlrichs, R., Bär, M., Horn, H. and Kölmel, C. 1989. Chem. Phys. Lett., 162: 165
77. Weigend, F. 2002. Phys. Chem. Chem. Phys., 4: 4285
78. Ahlrichs, R. 2004. Phys. Chem. Chem. Phys., 6: 5119
79. Arnim, M.V. and Ahlrichs, R. 1998. J. Comp. Chem., 19: 1746
80. Schäfer, A., Huber, C. and Ahlrichs, R. 1994. J. Chem. Phys., 100: 5829
81. Eichkorn, K., Weigend, F., Treutler, O. and Ahlrichs, R. 1997. Theor. Chem. Acc., 97: 119
82. Furche, F. and Ahlrichs, R. 2002. J. Chem. Phys., 117: 7433
83. Furche, F. and Ahlrichs, R. 2004. J. Chem. Phys., 121: 12772
84. Bauernschmitt, R. and Ahlrichs, R. 1996. Chem. Phys. Lett., 256: 454
85. Bauernschmitt, R., Häser, M., Treutler, O. and Ahlrichs, R. 1997. Chem. Phys. Lett., 264: 573
86. Grimme, S., Furche, F. and Ahlrichs, R. 2002. Chem. Phys. Lett., 361: 321
87. Rappoport, D. and Furche, F. 2005. J. Chem. Phys., 122: 064105
88. Treutler, O. and Ahlrichs, R. 1995. J. Chem. Phys., 102: 346
89. Deglmann, P., Furche, F. and Ahlrichs, R. 2002. Chem. Phys. Lett., 362: 511
90. Deglmann, P., May, K., Furche, F. and Ahlrichs, R. 2004. Chem. Phys. Lett., 384: 103
91. Hättig, C. 2003. J. Chem. Phys., 118: 7751
92. Köhn, A. and Hättig, C. 2003. J. Chem. Phys., 119: 5021
93. Klamt, A. and Schüürmann, G. 1993. J. Chem. Soc. Perkin Trans., 2: 799
94. Boys, S.F. and Bernardi, F. 1970. Mol. Phys., 19: 553
95. Zhou, L.C., Liu, J.Y., Zhao, G.J., Shi, Y., Peng, X.J. and Han, K.L. 2007. Chem. Phys., 333: 179
96. Renth, F., Siewertsen, R. and Temps, F. 2013. Int. Rev. Phys. Chem., 32: 1
97. Narayanan, S.S., Sarkar, R., Sinha, S.S., Dias, F., Monkman, A. and Pal, S.K. 2008. J. Phys. Chem. C, 112: 3423
98. Mitra, R.K., Verma, P.K. and Pal, S.K. 2009. J. Phys. Chem. B, 113: 4744
99. Wang, H.F., Wang, M.S., Liu, E., Xin, M. and Yang, C.L. 2011. Comput. Theor. Chem., 964: 243
100. Wang, H.F., Wang, M.S., Liu, E., Xin, M. and Yang, C.L. 2011. Cent. Eur. J. Phys., 9: 792
101. Tan, J.J., Hao, C., Wei, N.N., Zhang, M.X. and Dai, X.Y. 2011. J. Theor. Comput. Chem., 10: 1
102. Zhang, J.Z., Zhao, G.Y., Li, R.Z. and Hou, D.Y. 2011. J. Clust. Sci., 22: 501
103. Wang, D., Hao, C., Wang, S., Dong, H. and Qiu, J. 2012. Cent. Eur. J. Phys., 10: 116
104. Ma, M.X. and Yang, D.P. 2012. J. Clust. Sci., 23: 155
105. Zhang, X.Y. and Zhang, W. 2012. Mol. Simul., 38: 57
106. Liu, Y.H., Zhao, G.J., Li, G.Y. and Han, K.L. 2010. J. Photochem. Photobiol. A: Chem., 209: 181
107. Weisstuch, A. and Testa, C. 1968. J. Phys. Chem., 72: 1982
108. Inuzuka, K. and Fujimoto, A. 1986. Spectrochim. Acta, 42: 929
109. Kim, C., Schick, P. and Weber, P.M. 1995. J. Chem. Phys., 103: 6903
110. Hager, J. and Wallace, S.C. 1985. J. Phys. Chem., 89: 3833
111. Testa, C. and Wlld, U.P. 1981. J. Phys. Chem., 85: 2637
112. Chelli, R., Schettino, V. and Procacci, P. 2005. J. Chem. Phys., 122: 234107
113. Hung, F.T., Hu, W.P., Li, T.H., Cheng, C.C. and Chou, P.T. 2003. J. Phys. Chem. A, 107: 3244
114. Ishikawa, H., Iwata, K. and Hamaguchi, H. 2002. J. Phys. Chem. A, 106: 2305
115. Chang, H.C., Jiang, J.C., Lai, W.W., Lin, J.S., Chen, G.C., Tsai, W.C. and Lin, S.H. 2005. J. Phys. Chem. B, 109: 23103
116. Zielke, P. and Suhm, M.A. 2007. Phys. Chem. Chem. Phys., 9: 4528
117. Leiderman, P., Huppert, D. and Agmon, N. 2006. Biophys. J., 90: 1009
118. Coquet, R., Tada, M. and Iwasawa, Y. 2007. Phys. Chem. Chem. Phys., 9: 6040
119. Bartl, K., Funk, A., Schwing, K., Fricke, H., Kock, G., Martin, H.D. and Gerhards, M. 2009. Phys. Chem. Chem. Phys., 11: 1173
120. Chai, S., Zhao, G.J., Song, P., Yang, S.Q., Liu, J.Y. and Han, K.L. 2009. Phys. Chem. Chem. Phys., 11: 4385
121. Chu, T.S. and Han, K.L. 2005. J. Phys. Chem. A, 109: 2050
122. Chu, T.S. and Han, K.L. 2008. Phys. Chem. Chem. Phys., 10: 2431
123. Li, G.Y., Zhao, G.J., Liu, Y.H., Han, K.L. and He, G.Z. 2010. J. Comput. Chem., 31: 1759
124. Zimmermann Dimer, L.M. and Machado, V.G. 2009. Dyes Pigm., 82: 187
125. Yu, F., Li, P., Li, G., Zhao, G.J., Chu, T.S. and Han, K.L. 2011. J. Am. Chem. Soc., 133: 11030
126. De Silva, A.P., Gunaratne, H.Q.N., Gunnlaugsson, T., Huxley, A.J.M., McCoy, C.P., Rademacher, J.T. and Rice, T.E. 1997. Chem. Rev., 97: 1515
127. Schmidtchen, F.P. and Berger, M. 1997. Chem. Rev., 97: 1609
128. Peng, X.J., Wu, Y.K., Fan, J.L., Tian, M.Z. and Han, K.L. 2005. J. Org. Chem., 170: 10524
129. Swamy, K.M.K., Lee, Y.J., Lee, H.N., Chun, J., Kim, Y., Kim, S.J. and Yoon, J. 2006. J. Org. Chem., 71: 8626
130. Li, G.Y., Zhao, G.J., Han, K.L. and He, G.Z. 2011. J. Comput. Chem., 32: 668
131. Alkorta, I., Rozas, I. and Elguero, J. 1998. Chem. Soc. Rev., 27: 163
132. Custelcean, R. and Jackson, J.E. 2001. Chem. Rev., 101: 1963
133. Epstein, L.M. and Shubina, E.S. 2002. Coord. Chem. Rev., 231: 165
134. Belkova, N.V., Shubina, E.S. and Epstein, L.M. 2005. Acc. Chem. Res., 38: 624
135. Kubas, G.J. 2007. Proc. Natl. Acad. Sci. USA, 104: 6901
136. Kar, T. and Scheiner, S. 2003. J. Chem. Phys., 119: 1473
137. Sobczyk, L., Grabowski, S.J. and Krygowski, T.M. 2005. Chem. Rev., 105: 3513
138. Li, J.S., Zhao, F. and Jing, F.Q. 2002. J. Chem. Phys., 116: 25
139. Grabowski, S.J., Robinson, T.L. and Leszczynski, J. 2004. Chem. Phys. Lett., 386: 44
140. Alkorta, I., Zborowski, K., Elguero, J. and Solimannejad, M. 2006. J. Phys. Chem. A, 110: 10279
141. Zhang, M.L., Huang, Z.J. and Lin, Z.J. 2005. J. Chem. Phys., 122: 134313
142. Yu, W.B., Lin, Z.J. and Huang, Z.J. 2006. ChemPhysChem, 7: 828
143. Brown, M.P. and Heseltine, R.W. 1968. Chem. Commun., 1551
144. Patwari, G.N., Ebata, T. and Mikami, N. 2000. J. Chem. Phys., 113: 9885
145. Patwari, G.N., Ebata, T. and Mikami, N. 2001. J. Chem. Phys., 114: 8877
146. Patwari, G.N., Ebata, T. and Mikami, N. 2002. J. Chem. Phys., 116: 6056
147. Ebata, T., Mizuochi, N., Watanabe, T. and Mikami, N. 1996. J. Phys. Chem., 100: 546
148. Iwasaki, A., Fujii, A., Watanabe, T., Ebata, T. and Mikami, N. 1996. J. Phys. Chem., 100: 16053
149. Fujii, A., Ebata, T. and Mikami, N. 2002. J. Phys. Chem. A, 106: 8554
150. Patwari, G.N., Ebata, T. and Mikami, N. 2002. Chem. Phys., 283: 193
151. Patwari, G.N., Ebata, T. and Mikami, N. 2001. J. Phys. Chem. A, 105: 8462
152. Patwari, G.N., Fujii, A. and Mikami, N. 2006. J. Chem. Phys., 124: 241103
153. Zhao, G.J. and Han, K.L. 2007. J. Chem. Phys., 127: 024306
154. Wei, N.N., Hao, C., Xiu, Z.L., Chen, J.W. and Qiu, J.S. 2010. J. Comput. Chem., 31: 2853
155. Wei, N.N., Li, P., Hao, C., Wang, R., Xiu, Z., Chen, J. and Song, P. 2010. J. Photochem. Photobiol. A: Chem., 210: 77
156. Wei, N.N., Hao, C., Tan, J.J., Zhao, G.Y., Li, R.Z., Xiu, Z.L. and Qiu, J.S. 2011. J. Mol. Model., 17: 1891
157. Wei, N.N., Hao, C., Xiu, Z.L. and Qiu, J.S. 2010. Phys. Chem. Chem. Phys., 12: 9445
158. Han, K.L. and He, G.Z. 2007. J. Photochem. Photobiol. C: Photochem. Rev., 8: 55
159. Chu, T.S., Zhang, X. and Han, K.L. 2005. J. Chem. Phys., 122: 214301
160. Chu, T.S., Zhang, Y. and Han, K.L. 2006. Int. Rev. Phys. Chem., 25: 201
161. Chu, T.S., Han, K.L. and Schatz, G.C. 2007. J. Phys. Chem. A, 111: 8286