Experimental and theoretical studies of the photophysical properties of 2- and 2,7-functionalized pyrene derivatives

Journal of the American Chemical Society

Volumn 133, Issue 34, 2011, Pages 13349-13362

  Crawford, Andrew G ^a   Dwyer, Austin D ^a   Liu, Zhiqiang ^a,b   Steffen, Andreas ^a   Beeby, Andrew ^a   Pålsson, Lars Olof ^a   Tozer, David J ^a   Marder, Todd B ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

^b SHANDONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION AND EMISSION SPECTRA; ACID DERIVATIVE; FLUORESCENCE LIFETIMES; FLUORESCENCE QUANTUM YIELD; FUNCTIONALS; MOLECULAR PLANES; ORBITALS; PHOTOPHYSICAL PROPERTIES; PYRENE DERIVATIVES; THEORETICAL STUDY; TIME DEPENDENT DENSITY FUNCTIONAL THEORY;

BUTYRIC ACID; CARBON DIOXIDE; DENSITY FUNCTIONAL THEORY; EMISSION SPECTROSCOPY; FATTY ACIDS; FLUORESCENCE; QUANTUM YIELD;

PYRENE;

4 (PYREN 1 YL)BUTYRIC ACID; 4 (PYREN 2 YL)BUTYRIC ACID DERIVATIVE; PYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; EXPERIMENTAL STUDY; FLAME PHOTOMETRY; FLUORESCENCE; PHOTOCHEMISTRY; PHYSICAL CHEMISTRY; QUANTUM YIELD; THEORETICAL STUDY;

EID: 80052086022     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2006862     Document Type: Article

References (162)

1. Coventry, D. N.; Batsanov, A. S.; Goeta, A. E.; Howard, J. A. K.; Marder, T. B.; Perutz, R. N. Chem. Commun. 2005, 2172-2174
2. The application of these two compounds in the synthesis of the remaining 2- and 2,7-derivatives in the current paper will be reported shortly: Crawford, A. G.; Liu, Z.; Mkhalid, I. A. I.; Thibault, M.-H.; Schwarz, N.; Alcaraz, G.; Steffen, A.; Collings, J. C.; Marder, T. B. Manuscript in preparation, presented in part at Pacifichem 2010, Symposium (No. 35) on Organoboron, Organosilicon and Organophosphorus as Optoelectronic and Energy Related Materials, Honolulu, Dec 17, 2010; ID No. 590.
3. A synthesis and partial characterization of 1 has been reported previously: Klassen, S. E.; Daub, G. H.; VanderJagt, D. L. J. Org. Chem. 1983, 48, 4361-4366
4. A synthesis of 10 has been reported previously: Boldt, P.; Bruhnke, D. J. Prakt. Chem. 1994, 336, 110-114
5. Compound 16 has appeared in a patent: Seo, J. D.; Lee, K. H.; Kim, H. J.; Park, C. G.; Oh, H. Y. Eur. Pat. Appl. EP 1437395, 2004 (CAS no. 722499-18-5).
6. Compound 18 has been reported previously: Beinhoff, M.; Weigel, W.; Jurczok, M.; Rettig, W.; Modrakowski, C.; Brüdgam, I.; Hartl, H.; Schlüter, A. D. Eur. J. Org. Chem. 2001, 3819-3829
7. Compound 19 has been reported previously in ref 19.
8. A discussion regarding compound 21 can be found in ref 17f, vide infra.
9. Netzel, T. L.; Nafisi, K.; Headrick, J.; Eaton, B. E. J. Phys. Chem. 1995, 99, 17948-17955
10. Huber, R.; Fiebig, T.; Wagenknecht, H.-A. Chem. Commun. 2003, 1878-1879
11. Trifonov, A.; Buchvarov, I.; Wagenknecht, H.-A.; Fiebig, T. Chem. Phys. Lett. 2005, 409, 277-280
12. Kaden, P.; Mayer-Enthart, E.; Trifonov, A.; Fiebig, T.; Wagenknecht, H.-A. Angew. Chem., Int. Ed. 2005, 44, 1636-1639
13. Okamoto, A.; Tainaka, K.; Nishiza, K.-I.; Saito, I. J. Am. Chem. Soc. 2005, 127, 13128-13129
14. Valis, L.; Mayer-Enthart, E.; Wagenknecht, H.-A. Bioorg. Med. Chem. Lett. 2006, 16, 3184-3187
15. Malinovskii, V. L.; Häner, R. Eur. J. Org. Chem. 2006, 3550-3553
16. Seo, Y. J.; Rhee, H.; Joo, T.; Kim, B. H. J. Am. Chem. Soc. 2007, 129, 5244-5247
17. Malinovskii, V. L.; Samain, F.; Häner, R. Angew. Chem., Int. Ed. 2007, 46, 4464-4467
18. Bittermann, H.; Siegemund, D.; Malinovskii, V. L.; Häner, R. J. Am. Chem. Soc. 2008, 130, 15285-15287
19. Nakamura, M.; Fukunaga, Y.; Sasa, K.; Ohtoshi, Y.; Kanaori, K.; Hayashi, H.; Nakano, H.; Yamana, K. Nucleic Acids Res. 2005, 33, 5887-5895
20. Nakamura, M.; Ohtoshi, Y.; Yamana, K. Chem. Commun. 2005, 5163-5165
21. Nakamura, M.; Shimomura, Y.; Ohtoshi, Y.; Sasa, K.; Hayashi, H.; Nakano, H.; Yamana, K. Org. Biomol. Chem. 2007, 5, 1945-1951
22. Kool, E. T.; Morales, J. C.; Guckian, K. M. Angew. Chem., Int. Ed. 2000, 39, 990-1009
23. Wilson, J. N.; Gao, J.; Kool, E. T. Tetrahedron 2007, 63, 3427-3433
24. Mayer-Enthart, E.; Wagner, C.; Barbaric, J.; Wagenknecht, H.-A. Tetrahedron 2007, 63, 3434-3439
25. Teo, Y. N.; Wilson, J. N.; Kool, E. T. J. Am. Chem. Soc. 2009, 131, 3923-3933
26. Samain, F.; Ghosh, S.; Teo, Y. N.; Kool, E. T. Angew. Chem., Int. Ed. 2010, 49, 7025-7029
27. Okamoto, A.; Kanatani, K.; Saito, I. J. Am. Chem. Soc. 2004, 126, 4820-4827
28. Kashida, H.; Asanuma, H.; Komiyama, M. Chem. Commun. 2006, 2768-2770
29. Kalyanasundaram, K.; Thomas, J. K. J. Am. Chem. Soc. 1977, 99, 2039-2044
30. Kalyanasundaram, K. Photochemistry in Microheterogeneous Systems, Academic Press: Orlando, FL, 1987; pp 39-41.
31. Perry, M.; Carra, C.; Chrétien, M. N.; Scaiano, J. C. J. Phys. Chem. A 2007, 111, 4884-4889
32. Vaughan, W. M.; Weber, G. Biochemistry 1970, 9, 464-473
33. Ribou, A.-C.; Vigo, J.; Salmon, J.-M. Photochem. Photobiol. 2004, 80, 274-280
34. Berezin, M. Y.; Achilefu, S. Chem. Rev. 2010, 110, 2641-2684
35. Flamm, M.; Schachter, D. Nature 1982, 298, 290-292
36. Fujimori, E.; Shambaugh, N. Biochim. Biophys. Acta 1983, 742, 155-161
37. Lee, J. A.; Fortes, P. A. G. Biochemistry 1985, 24, 322-330
38. Ebata, K.; Masuko, M.; Ohtani, H.; Kashiwasake-Jibu, M. Photochem. Photobiol. 1995, 62, 836-839
39. Sugahara, D.; Amano, J.; Irimura, T. Anal. Sci. 2003, 19, 167-169
40. Takeuchi, T.; Kosuge, M.; Tadokoro, A.; Sugiura, Y.; Nishi, M.; Kawata, M.; Sakai, N.; Matile, S.; Futaki, S. ACS Chem. Biol. 2006, 1, 299-303
41. Jablonski, A. E.; Kawakami, T.; Ting, A. Y.; Payne, C. K. J. Phys. Chem. Lett. 2010, 1, 1312-1315
42. Kim, H. J.; Bok, J. H.; Vicens, J.; Suh, I.-H.; Ko, J.; Kim, J. S. Tetrahedron Lett. 2005, 46, 8765-8768
43. Ben Othman, A.; Lee, J. W.; Huh, Y.-D.; Abidi, R.; Kim, J. S.; Vicens, J. Tetrahedron 2007, 63, 10793-10800
44. Ben Othman, A.; Lee, J. W.; Wu, J. S.; Kim, J. S.; Abidi, R.; Thuéry, P.; Strub, J. M.; Van Dorsselaer, A.; Vicens, J. J. Org. Chem. 2007, 72, 7634-7640
45. Park, S. Y.; Yoon, J. H.; Hong, C. S.; Souane, R.; Kim, J. S.; Matthews, S. E.; Vicens, J. J. Org. Chem. 2008, 73, 8212-8218
46. Kim, H. J.; Hong, J.; Hong, A.; Ham, S.; Lee, J. H.; Kim, J. S. Org. Lett. 2008, 10, 1963-1966
47. Leray, I.; Valeur, B. Eur. J. Inorg. Chem. 2009, 3525-3535
48. Jung, H. S.; Park, M.; Han, D. Y.; Kim, E.; Lee, C.; Ham, S.; Kim, J. S. Org. Lett. 2009, 11, 3378-3381
49. Yu, C.; Yam, V. W.-W. Chem. Commun. 2009, 1347-1349
50. Lee, Y. H.; Liu, H.; Lee, J. Y.; Kim, S. H.; Kim, S. K.; Sessler, J. L.; Kim, Y.; Kim, J. S. Chem.-Eur. J. 2010, 16, 5895-5901
51. Suzuki, K.; Seno, A.; Tanabe, H.; Ueno, K. Synth. Met. 2004, 143, 89-96
52. Oyamada, T.; Uchiuzou, H.; Akiyama, S.; Oku, Y.; Shimoji, N.; Matsushige, K.; Sasabe, H.; Adachi, C. J. Appl. Phys. 2005, 98, 074506
53. Thomas, K. R. J.; Velusamy, M.; Lin, J. T.; Chuen, C. H.; Tao, Y.-T. J. Mater. Chem. 2005, 15, 4453-4459
54. Muccini, M. Nat. Mater. 2006, 5, 605-613
55. Yang, C.-H.; Guo, T.-F.; Sun, I.-W. J. Lumin. 2007, 124, 93-98
56. Zhao, S.-B.; Wucher, P.; Hudson, Z. M.; McCormick, T. M.; Liu, X.-Y.; Wang, S.; Feng, X.-D.; Lu, Z.-H. Organometallics 2008, 27, 6446-6456
57. Wee, K.-R.; Ahn, H.-C.; Son, H.-J.; Han, W.-S.; Kim, J.-E.; Cho, D. W.; Kang, S. O. J. Org. Chem. 2009, 74, 8472-8475
58. Sonar, P.; Soh, M. S.; Cheng, Y. H.; Henssler, J. T.; Sellinger, A. Org. Lett. 2010, 12, 3292-3295
59. Zhou, Y.; Kim, J. W.; Kim, M. J.; Son, W.-J.; Han, S. J.; Kim, H. N.; Han, S.; Kim, Y.; Lee, C.; Kim, S.-J.; Kim, D. H.; Kim, J.-J.; Yoon, J. Org. Lett. 2010, 12, 1272-1275
60. for a review on pyrene-based materials for organic electronics, see: Figueira-Duarte, T. M.; Müllen, K. Chem. Rev. 2011, doi: 10.1021/cr100428a.
61. Banerjee, M.; Vyas, V. S.; Lindeman, S. V.; Rathore, R. Chem. Commun. 2008, 1889-1891
62. Yang, S.-W.; Elangovan, A.; Hwang, K.-C.; Ho, T.-I. J. Phys. Chem. B 2005, 109, 16628-16635
63. Venkataramana, G.; Sankararaman, S. Eur. J. Org. Chem. 2005, 4162-4166
64. Leroy-Lhez, S.; Fages, F. Eur. J. Org. Chem. 2005, 2684-2688
65. Shimizu, H.; Fujimoto, K.; Furusyo, M.; Maeda, H.; Nanai, Y.; Mizuno, K.; Inouye, M. J. Org. Chem. 2007, 72, 1530-1533
66. Kim, H. M.; Lee, Y. O.; Lim, C. S.; Kim, J. S.; Cho, B. R. J. Org. Chem. 2008, 73, 5127-5130
67. Wanninger-Weiß, C.; Wagenknecht, H.-A. Eur. J. Org. Chem. 2008, 64-71
68. Astakhova, I. V.; Korshun, V. A. Russ. J. Bioorg. Chem. 2008, 34, 510-512
69. Filichev, V. V.; Astakhova, I. V.; Malakhov, A. D.; Korshun, V. A.; Pedersen, E. B. Chem.-Eur. J. 2008, 14, 9968-9980
70. Astakhova, I. V.; Lindegaard, D.; Korshun, V. A.; Wengel, J. Chem. Commun. 2010, 46, 8362-8364
71. After our paper was submitted, the following paper appeared: Qiao, Y.; Zhang, J.; Xu, W.; Zhu, D. Tetrahedron 2011, 67, 3395-3405
72. Runge, E.; Gross, E. K. U. Phys. Rev. Lett. 1984, 52, 997-1000
73. Casida, M. E. Recent Advances in Density Functional Theory: Part 1; World Scientific: Singapore, 1995; pp 155-192.
74. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
75. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
76. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211
77. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
78. Yanai, T.; Tew, D. P.; Handy, N. C. Chem. Phys. Lett. 2004, 393, 51-57
79. Goodpaster, J. V.; Harrison, J. F.; McGuffin, V. L. J. Phys. Chem. A 1998, 102, 3372-3381
80. Bito, Y.; Shida, N.; Toru, T. Chem. Phys. Lett. 2000, 328, 310-315
81. Parac, M.; Grimme, S. Chem. Phys. 2003, 292, 11-21
82. Grimme, S.; Parac, M. ChemPhysChem 2003, 4, 292-295
83. Wang, B.-C.; Chang, J.-C.; Tso, H.-C.; Hsu, H.-F.; Cheng, C.-Y. J. Mol. Struct.: THEOCHEM 2003, 629, 11-20
84. Dierksen, M.; Grimme, S. J. Chem. Phys. 2004, 120, 3544-3554
85. Park, Y. H.; Cheong, B.-S. Curr. Appl. Phys. 2006, 6, 700-705
86. Kerkines, I. S. K.; Petsalakis, I. D.; Theodorakopoulos, G.; Klopper, W. J. Chem. Phys. 2009, 131, 224315
87. Bazyl, O. K.; Maier, G. V.; Kopylova, T. N.; Danilova, V. I. Zh. Prikl. Spektr. 1982, 37, 80-86
88. Grimme, S; Neese, F. J. Chem. Phys. 2007, 127, 154116
89. Matsumi, N.; Naka, K.; Chujo, Y. J. Am. Chem. Soc. 1998, 120, 5112-5113
90. Noda, T.; Ogawa, H.; Shirota, Y. Adv. Mater. 1999, 11, 283-285
91. Shirota, Y.; Kinoshita, M.; Noda, T.; Okumoto, K.; Ohara, T. J. Am. Chem. Soc. 2000, 122, 11021-11022
92. Entwistle, C. D.; Marder, T. B. Angew. Chem., Int. Ed. 2002, 41, 2927-2931 and references therein
93. Entwistle, C. D.; Marder, T. B. Chem. Mater. 2004, 16, 4574-4585
94. Qin, Y.; Cheng, G.; Achara, O.; Parab, K.; Jäkle, F. Macromolecules 2004, 37, 7123-7131
95. Parab, K.; Qin, Y.; Haleem, S.; Jäkle, F. Polym. Mater. Sci. Eng. Prepr. 2005, 93, 422-423
96. Liu, X. Y.; Bai, D. R.; Wang, S. Angew. Chem., Int. Ed. 2006, 45, 5475-5478
97. Jäkle, F. Coord. Chem. Rev. 2006, 250, 1107-1121
98. Wakamiya, A.; Mori, K.; Yamaguchi, S. Angew. Chem., Int. Ed. 2007, 46, 4273-4276
99. Haussler, M.; Tang, B. Z. Adv. Polym. Sci. 2007, 209, 1-58
100. Elbing, M.; Bazan, G. C. Angew. Chem., Int. Ed. 2008, 47, 834-838
101. Yuan, Z.; Taylor, N. J.; Marder, T. B.; Williams, I. D.; Kurtz, S. K.; Cheng, L.-T. J. Chem. Soc., Chem. Commun. 1990, 1489-1492
102. Yuan, Z.; Taylor, N. J.; Marder, T. B.; Williams, I. D.; Kurtz, S. K.; Cheng, L.-T. In Organic Materials for Non-linear Optics II; Hann, R. A.; Bloor, D., Eds.; Royal Society of Chemistry: Cambridge, U.K., 1991; pp 190-196.
103. Yuan, Z.; Taylor, N. J.; Sun, Y.; Marder, T. B.; Williams, I. D.; Cheng, L.-T. J. Organomet. Chem. 1993, 449, 27-37
104. Yuan, Z.; Taylor, N. J.; Ramachandran, R.; Marder, T. B. Appl. Organomet. Chem. 1996, 10, 305-316
105. Yuan, Z.; Collings, J. C.; Taylor, N. J.; Marder, T. B.; Jardin, C.; Halet, J.-F. J. Solid State Chem. 2000, 154, 5-12
106. Yuan, Z.; Entwistle, C. D.; Collings, J. C.; Albesa-Jové, D.; Batsanov, A. S.; Howard, J. A. K.; Kaiser, H.-M.; Kaufmann, D. E.; Poon, S.-Y.; Wong, W.-Y.; Jardin, C.; Fathallah, S.; Boucekkine, A.; Halet, J.-F.; Marder, T. B. Chem.-Eur. J. 2006, 12, 2758-2771
107. Zhou, G.; Ho, C.-L.; Wong, W.-Y.; Wang, Q.; Ma, D.; Wang, L.; Lin, Z.; Marder, T. B.; Beeby, A. Adv. Funct. Mater. 2008, 18, 499-511
108. Weber, L.; Werner, V.; Fox, M. A.; Marder, T. B.; Schwedler, S.; Brockhinke, A.; Stammler, H.-G.; Neumann, B. Dalton Trans. 2009, 2823-2831
109. Braunschweig, H.; Herbst, T.; Rais, D.; Ghosh, S.; Kupfer, T.; Radacki, K.; Crawford, A. G.; Ward, R. M.; Marder, T. B.; Fernández, I.; Frenking, G. J. Am. Chem. Soc. 2009, 131, 8989-8999
110. Charlot, M.; Porrés, L.; Entwistle, C. D.; Beeby, A.; Marder, T. B.; Blanchard-Desce, M. Phys. Chem. Chem. Phys. 2005, 7, 600-606
111. Porrés, L.; Charlot, M.; Entwistle, C. D.; Beeby, A.; Marder, T. B.; Blanchard-Desce, M. Proc. SPIE-Int. Soc. Opt. Eng. 2005, 92, 5934-5936
112. Collings, J. C.; Poon, S.-Y.; Le Droumaguet, C.; Charlot, M.; Katan, C.; Pålsson, L.-O.; Beeby, A.; Mosely, J. A.; Kaiser, H.-M.; Kaufmann, D.; Wong, W.-Y.; Blanchard-Desce, M.; Marder, T. B. Chem.-Eur. J. 2009, 15, 198-208
113. Entwistle, C. D.; Collings, J. C.; Steffen, A.; Pålsson, L.-O.; Beeby, A.; Albesa-Jové, D.; Burke, J. M.; Batsanov, A. S.; Howard, J. A. K.; Mosely, J. A.; Poon, S.-Y.; Wong, W.-Y.; Ibersiene, F.; Fathallah, S.; Boucekkine, A.; Halet, J.-F.; Marder, T. B. J. Mater. Chem. 2009, 40, 7532-7544
114. Stolka, M.; McGrane, K. M.; Facci, J. S. Photoconductive Imaging Members with Alkoxy Amine Charge Transport Molecules. U.S. Patent 4,588,666, May 13, 1986
115. Bellmann, E.; Shaheen, S. E.; Thayumanavan, S.; Barlow, S.; Grubbs, R. H.; Marder, S. R.; Kippelen, B.; Peyghambarian, N. Chem. Mater. 1998, 10, 1668-1676
116. Mitschke, U.; Bäuerle, P. J. Mater. Chem. 2000, 10, 1471-1507
117. Low, P. J.; Paterson, M. A. J.; Puschmann, H.; Goeta, A. E.; Howard, J. A. K.; Lambert, C.; Cherryman, J. C.; Tackley, D. R.; Leeming, S.; Brown, B. Chem.-Eur. J. 2004, 10, 83-91
118. Bardecker, J. A.; Ma, H.; Kim, T.; Huang, F.; Liu, M. S.; Cheng, Y.-J.; Ting, G.; Jen, A. K.-Y. Adv. Funct. Mater. 2008, 18, 3964-3971
119. Nguyen, P.; Yuan, Z.; Agocs, L.; Lesley, G.; Marder, T. B. Inorg. Chim. Acta 1994, 220, 289-296
120. Khan, M. S.; Kakkar, A. K.; Long, N. J.; Lewis, J.; Raithby, P.; Nguyen, P.; Marder, T. B.; Wittmann, F.; Friend, R. H. J. Mater. Chem. 1994, 4, 1227-1232
121. Nguyen, P.; Lesley, G.; Marder, T. B.; Ledoux, I.; Zyss, J. Chem. Mater. 1997, 9, 406-408
122. Biswas, M.; Nguyen, P.; Marder, T. B.; Khundkar, L. R. J. Phys. Chem. A 1997, 101, 1689-1695
123. Li, H.; Powell, D. R.; Firman, T. K.; West, R. Macromolecules 1998, 31, 1093-1098
124. Bunz, U. H. F. Chem. Rev. 2000, 100, 1605-1644
125. Donhauser, Z. J.; Mantooth, B. A.; Kelly, K. F.; Bumm, L. A.; Monnell, J. D.; Stapleton, J. J.; Price, D. W., Jr.; Rawlett, A. M.; Allara, D. L.; Tour, J. M.; Weiss, P. S. Science 2001, 292, 2303-2307
126. Dirk, S. M.; Price, D. W., Jr.; Chanteau, S.; Kosynkin, D. V.; Tour, J. M. Tetrahedron 2001, 57, 5109-5121
127. Kim, J.; Swager, T. M. Nature 2001, 411, 1030-1034
128. Schmitz, C.; Pösch, P.; Thelakkat, M.; Schmidt, H.-W.; Montali, A.; Feldman, K.; Smith, P.; Weder, C. Adv. Funct. Mater. 2001, 11, 41-46
129. Levitus, M.; Schmieder, K.; Ricks, H.; Shimizu, K. D.; Bunz, U. H. F.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2001, 123, 4259-4265
130. Beeby, A.; Findlay, K. S.; Low, P. J.; Marder, T. B.; Matousek, P.; Parker, A. W.; Rutter, S. R.; Towrie, M. Chem. Commun. 2003, 2406-2407
131. Nakatsuji, S.; Matsuda, K.; Uesugi, Y.; Nakashima, K.; Akiyama, S.; Fabian, W. J. Chem. Soc., Perkin Trans. 1 1992, 7, 755-758
132. Nguyen, P.; Todd, S.; van den Biggelaar, D.; Taylor, N. J.; Marder, T. B.; Wittmann, F.; Friend, R. H. Synlett 1994, 299-301
133. Kawai, T.; Sasaki, T.; Irie, M. Chem. Commun. 2001, 711-712
134. Schmieder, K.; Levitus, M.; Dang, H.; Garcia-Garibay, M. A. J. Phys. Chem. A 2002, 106, 1551-1556
135. Giménez, R.; Piñol, M.; Serrano, J. L. Chem. Mater. 2004, 16, 1377-1383
136. Beeby, A.; Findlay, K. S.; Goeta, A. E.; Porrés, L.; Rutter, S. R.; Thompson, A. L. Photochem. Photobiol. Sci. 2007, 6, 982-986
137. Siddle, J. S.; Ward, R. M.; Collings, J. C.; Rutter, S. R.; Porrés, L.; Applegarth, L.; Beeby, A.; Batsanov, A. S.; Thompson, A. L.; Howard, J. A. K.; Boucekkine, A.; Costuas, K.; Halet, J.-F.; Marder, T. B. New J. Chem. 2007, 31, 841-851
138. Matano, Y.; Nakashima, M.; Imahori, H. Angew. Chem., Int. Ed. 2009, 48, 4002-4005
139. Steffen, A.; Tay, M. G.; Batsanov, A. S.; Howard, J. A. K.; Beeby, A.; Vuong, K. Q.; Sun, X.-Z.; George, M. W.; Marder, T. B. Angew. Chem., Int. Ed. 2010, 49, 2349-2353
140. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890-931
141. Yoshinaga, T.; Hiratsuka, H.; Tanizaki, Y. Bull. Chem. Soc. Jpn. 1977, 50, 3096-3102
142. Turro, N. J.; Ramamurthy, V.; Scaiano, J. C. Principles of Molecular Photochemistry, An Introduction; University Science Books: Sausalito, CA, 2009.
143. Birks, J. B. Photophysics of Aromatic Molecules; Wiley-Interscience: London, 1970.
144. Values measured by the authors.
145. Michl, J.; Thulstrup, E. W. Spectroscopy with Polarized Light; VCH Publishers Inc.: New York, 1986; p 368.
146. Klessinger, M.; Michl, J. Excited States and Photochemistry of Organic Molecules; Wiley-VCH: New York, 1995; Chapters 1 and 2.
147. Clar, E. Polycyclic Hydrocarbons; Academic Press: London, 1964.
148. Platt, J. R. J. Chem. Phys. 1949, 17, 484-495
149. Platt, J. R. J. Opt. Soc. Am. 1953, 43, 252-257
150. Moffitt, W. J. Chem. Phys. 1954, 22, 320-333
151. Nakajima, A. Bull. Chem. Soc. Jpn. 1971, 44, 3272-3277
152. Foggi, P.; Pettini, L.; Sánta, I.; Righini, R.; Califano, S. J. Phys. Chem. 1995, 99, 7439-7445
153. Iikura, H.; Tsuneda, T.; Yanai, T.; Hirao, K. J. Chem. Phys. 2001, 115, 3540-3544
154. Peach, M. J. G.; Benfield, P.; Helgaker, T.; Tozer, D. J. J. Chem. Phys. 2008, 128, 044118
155. Wiggins, P.; Williams, J. A. G.; Tozer, D. J. J. Chem. Phys. 2009, 131, 091101
156. Beeby, A.; Findlay, K.; Low, P. J.; Marder, T. B. J. Am. Chem. Soc. 2002, 124, 8280-8284
157. Greaves, S. J.; Flynn, E. L.; Futcher, E. L.; Wrede, E.; Lydon, D. P.; Low, P. J.; Rutter, S. R.; Beeby, A. J. Phys. Chem. A 2006, 110, 2114-2121
158. Weber, L.; Werner, V.; Fox, M. A.; Marder, T. B.; Schwedler, S.; Brockhinke, A.; Stammler, H.-G.; Neumann, B. Dalton Trans. 2009, 1339-1351
159. Porrés, L.; Holland, A.; Pålsson, L.-O.; Monkman, A. P.; Kemp, C.; Beeby, A. J. Fluoresc. 2006, 16, 267-272
160. O'Connor, D. V.; Phillips, D. Time-correlated Single Photon Counting; Academic Press: New York, 1984.
161. Frisch, M. J.; et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004. The complete reference is given in the Supporting Information.
162. Dalton, a molecular electronic structure program, release 2.0, 2005; see http://www.kjemi.uio.no/software/dalton/dalton.html.