Toward designed singlet fission: Electronic states and photophysics of 1,3-diphenylisobenzofuran

Journal of Physical Chemistry A

Volumn 114, Issue 3, 2010, Pages 1457-1473

  Schwerin, Andrew F ^a   Johnson, Justin C ^b   Smith, Millicent B ^a   Sreearunothai, Paiboon ^c   Popović, Duška ^a   Černý, Jiří ^d   Havias, Zdeněk ^d   Paci, Irina ^e   Akdag, Akin ^a   MacLeod, Matthew K ^a   Chen, Xudong ^a   David, Donald E ^a   Ratner, Mark A ^e   Miller, John R ^c   Nozik, Arthur J ^b   Michl, Josef ^a,d  

^a UNIVERSITY OF COLORADO   (United States)

^b NATIONAL RENEWABLE ENERGY LABORATORY   (United States)

^c BROOKHAVEN NATIONAL LABORATORY   (United States)

^d INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^e NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AB INITIO; ABSORPTION BAND; ABSORPTION TRANSITIONS; ELECTRONIC EXCITATION; FLUORESCENCE EXCITATION SPECTRA; FLUORESCENCE POLARIZATION; FLUORESCENCE QUANTUM YIELD; FRANCK-CONDON; GROUND STATE GEOMETRY; INITIAL STATE; LINEAR DICHROISM; MAGNETIC CIRCULAR DICHROISMS; MODEL COMPOUND; MOLECULAR GEOMETRIES; NON-RADIATIVE CHANNELS; PHOTOPHYSICAL PROPERTIES; PHOTOPHYSICS; POLARIZED COMPONENTS; RADICAL CATIONS; SEMI-EMPIRICAL; SINGLET EXCITED STATE; TERMINAL STATE; TRANSITION INTENSITY; TRIPLET EXCITATION; TRIPLET STATE; UV VISIBLE ABSORPTION SPECTRUM; VISIBLE ABSORPTION SPECTRA;

ABSORPTION; ABSORPTION SPECTROSCOPY; CRYSTAL STRUCTURE; DICHROISM; ELECTRIC EXCITATION; ENERGY DISSIPATION; EXCITATION ENERGY; EXCITED STATES; FLUORESCENCE; GROUND STATE; LIGHT ABSORPTION; SINGLE CRYSTALS;

ELECTRON ENERGY LOSS SPECTROSCOPY;

1,3 DIPHENYLISOBENZOFURAN; 1,3-DIPHENYLISOBENZOFURAN; BENZOFURAN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; ELECTRON; PHOTOCHEMISTRY; QUANTUM THEORY; TEMPERATURE; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY CRYSTALLOGRAPHY;

BENZOFURANS; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; ELECTRONS; MODELS, MOLECULAR; PHOTOCHEMISTRY; QUANTUM THEORY; SPECTROPHOTOMETRY, ULTRAVIOLET; TEMPERATURE;

EID: 77249154697     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp907401t     Document Type: Article

References (82)

1. Nozik, A. J.; Ellingson, R. J.; Micic, O. I.; Blackburn, J. L.; Yu, P.; Murphy, J. E.; Beard, M. C.; Rumbles, G. Proceedings of the 27th DOE Solar Photochemistry Research Conference, June 6-9, 2004, Airline Conference Center, Warrenton, VA; 2004; pp 63-66. Available on line: http://www.sc.doe.gov/ BES/chm/Publications/Contractors%20Meetings/ 27th-DOE-Solar-Photochemistry-crop. pdf.
2. Michl, J.; Chen, X.; Rana, G.; Popović, D. B.; Downing, J.; Nozik, A. J.; Johnson, J. C.; Ratner, M. A.; Paci, I. Book of Abstracts, DOE Solar Program Review Meetings, October 24-28, 2004, Denver, CO; U.S. Department of Energy: Washington, DC, 2004; p 5.
3. Johnson, J. C.; Nozik, A. J.; Paci, I.; Ratner, M. A.; Popović, D. B.; David, D. E.; Chen, X.; Rana, G.; Michl, J. Book of Abstracts, International Chemical Congress of Pacific Basin Societies, Honolulu, III, December 15-20, 2005; Scholar One, Inc.: Charlottesville, VA, 2005; abstract 1597.
4. Paci, I.; Johnson, J. C.; Chen, X.; Rana, G.; Popović, D.; David, D. E.; Nozik, A. J.; Ratner, M. A.; Michl, J. J. Am. Chem. Soc. 2006, 128, 16546-16553.
5. Singh, S.; Jones, W. J.; Siebrand, W.; Stoicheff, B. P.; Schneider, W. G. J. Chem. Phys. 1965, 42, 330-342.
6. Swenberg, C. E.; Geacintov, N. E. In Organic Molecular Photophysics, Birks, J. B., Ed.; Wiley: New York, 1973; Vol.1, pp 489-564.
7. Hanna, M. C.; Nozik, A. J. J. Appl. Phys. 2006, 100, 074510-074518.
8. Shockley, W.; Queisser, H. J. J. Appl. Phys. 1961, 32, 510-519.
9. Nozik, A. J. Physica E 2002, 14, 115-120.
10. Ellingson, R. J.; Beard, M. C.; Johnson, J. C.; Yu, P.; Micic, O. I.; Nozik, A. J.; Shabaev, A.; Efros, A. L. Nano Lett. 2005, 5, 865-871.
11. Schaller, R. D.; Klimov, V. I. Phys. Rev. Lett. 2004, 92, 186601-1186601-1186604
12. Nozik, A. J. Chem. Phys. Lett. 2008, 457, 3-11.
13. Müller, A. M.; Avlasevich, Y. A.; Müllen, K.; Bardeen, C. J. Chem. Phys. Lett. 2006, 421, 518-522.
14. Müller, A. M.; Avlasevich, Y. A.; Schuller, W. W.; Müllen, K.; Bardeen, C. J. J. Am. Chem. Soc. 2007, 129, 14240-14250.
15. Michl, J.; Nozik, A. J.; Chen, X.; Johnson, J. C.; Rana, G.; Akdag, A.; Schwerin, A. F. In Organic Photovoltaics VIII; Kafafi, Z. H., Lane, P. A., Eds.; Proceedings of SPIE, Vol.6656; SPIE: Bellingham, WA, 2007; pp66560E1-66560E9.
16. Greyson, E. C.; Stepp, B. R.; Chen, X.; Schwerin, A. F.; Paci, I.; Smith, M. B.; Akdag, A.; Johnson, J. C.; Nozik, A. J.; Michl, J.; Ratner, M. A. J. Phys. Chem. B, in press.
17. Greyson, E. C.; Vura-Weis, J.; Michl, J.; Ratner, M. A. J. Phys. Chem. B., in press.
18. Johnson, J. C.; Akdag, A.; Chen, X.; Smith, M. B.; Schwerin, A. F.; Paci, I.; Nozik, A. J.; Ratner, M. A.; Michl, J. Unpublished results.
19. Johnson, J. C.; Smith, M. B.; Akdag, A.; Nozik, A. J.; Michl, J., Unpublished results.
20. Marciniak, H.; Fiebig, M.; Huth, M.; Schiefer, S.; Nickel, B.; Selmaier, F.; Lochbrunner, S. Phys. Rev. Lett. 2007, 99, 176402-1-4.
21. Thorsmølle, V. K.; Averitt, R. D.; Demsar, J.; Smith, D. L.; Tretiak, S.; Martin, R. L.; Chi, X.; Crone, B. K.; Ramirez, A. P.; Taylor, A. J. Phys. Rev. Lett. 2009, 102, 017401-1-4.
22. Herkstroeter, W. G.; Merkel, P. B. J. Photochem. 1981, 16, 331-341.
23. Howard, J. A.; Mendenhall, G. D. Can. J. Chem. 1975, 53, 2199-2201.
24. Ziebig, R.; Pragst, F. Z. Phys. Chem. (Leipzig) 1979, 260, 795-803.
25. Murray, E. C.; Keller, R. N. J. Org. Chem. 1969, 34, 2234-2235.
26. Michl, J.; Thulstrup, E. W. Spectroscopy with Polarized Light. Solute Alignment by Photoselection, in Liquid Crystals, Polymers, and Membranes, 2nd ed.; VCH Publishers: Deerfield Beach, FL, 1995; (a) eq 1.24, p 28;
27. (b) eq 1.130, 66;
28. (c) 156
29. (d) eq 7.125, 320
30. (e) 232
31. (f) 135
32. (g) 230 and 404
33. (h) 195
34. Fischer, M.; Georges, J. Chem. Phys. Lett. 1996, 260, 115-118.
35. Eaton, D. F. Pure Appl. Chem. 1988, 60, 1107-1114.
36. David, D. E.; Popović, D. B.; Antic, D.; Michl, J. J. Chem. Phys. 2004, 121, 10542-10550.
37. Wishart, J. F. In Radiation Chemistry: Present Status and Future Trends; Jonah, C. D., Rao, B. S. M., Eds.; Elsevier Science: Amsterdam, 2001; Vol.87, pp 21-35.
38. Wishart, J. F.; Cook, A. R.; Miller, J. R. Rev. Sci. Instrum. 2004, 75, 4359-4366.
39. Miller, J. R.; Penfield, K.; Johnson, M.; Closs, G.; Green, N. In Photochemistry and Radiation Chemistry. Complementary Methods for the Study of Electron Transfer; Wishart, J. F., Nocera, D. G., Eds.; American Chemical Society: Washington. DC, 1998; Vol.254, pp 161-176.
40. Takeda, N.; Asaoka, S.; Miller, J. R. J. Am. Chem. Soc. 2006, 128, 16073-16082.
41. Allen, A. O. Natl Stand. Ref. Data Ser. 1976, 57, 16-41.
42. Baxendale, J. H.; Beaumond, D.; Rodgers, M. A. J. Tram. Faraday Soc. 1970, 66, 1996-2003.
43. Dodelet, J. P.; Freeman, G. R. Can. J. Chem. 1975, 53, 1263-1274.
44. Asaoka, S.; Takeda, N.; Iyoda, T.; Cook, A. R.; Miller, J. R. J. Am. Chem. Soc. 2008, 130, 11912-11920.
45. De Waele, V.; Sorgues, S.; Pernot, P.; Marignier, J. L.; Monard, H.; Larbre, J. P.; Mostafavi, M. Chem. Phys. Lett. 2006, 423, 30-34.
46. Bruker SAINT; Bruker AXS Inc.: Madison, WI, 2001.
47. Bruker XPREP; Bruker AXS Inc.: Madison, WI, 2004.
48. Sheldrick G. M. SADABS; University of Göttingen: Göttingen, Germany, 2004.
49. Sheldrick G. M. SHELXTL, Version 6; Bruker AXS Inc.: Madison, WI, 2001.
50. Pariser, R.; Parr, R. G. J. Chem. Phys. 1953, 21, 466-471, 767-776.
51. Pople, J. A. Trans. Faraday Soc. 1953, 49, 1375-1385.
52. Castellan, A.; Michl, J. J. Am. Chem. Soc. 1978, 100, 6824-6827, and references therein.
53. Frisch, M. J. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
54. Eichkom, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 242, 652-660;
55. Chem. Phys. Lett. 1995, 242, 283.
56. Treutler, O.; Ahlrichs, R. J. Chem. Phys. 1995, 102, 346-354.
57. Eichkom, K.; Weigend, F.; Treutler, O.; Ahlrichs, R. Theor. Chem. Acc. 1997, 97, 119-124.
58. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
59. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
60. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
61. Christiansen, O.; Koch, H.; Jørgensen, P. Chem. Phys. Lett. 1995, 243, 409-418.
62. Hättig, C.; Weigend, F. J. Chem. Phys. 2000, 113, 5154-5161.
63. Hättig, C. J. Chem. Phys. 2003, 118, 7751-7761.
64. Weigend, F.; Häser, M.; Patzelt, H.; Ahlrichs, R. Chem. Phys. Lett. 1998, 294, 143-152.
65. Weigend, F.; Häser, M. Theor. Chem. Acc. 1997, 97, 331-340.
66. Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, C. Chem. Phys. Lett. 1989, 162, 165-169.
67. Pierloot, K.; Dumez, B.; Widmark, P.-O.; Roos, B. O. Theor. Chim. Acta 1995, 90, 87-114.
68. Karlström, G.; Lindh, R.; Malmqvist, P.-Å.; Roos, B. O.; Ryde, U.; Veryazov, V.; Widmark, P.-O.; Cossi, M.; Schimmelpfennig, B.; Neogrady, P.; Scijo, L. Comput. Mater. Sci. 2003, 28, 222-239.
69. Hättig, C.; Hald, K. Phys. Chem. Chem. Phys. 2002, 4, 2111-2118.
70. Köhn, A.; Hättig, C. J. Chem. Phys. 2003, 119, 5021-5036.
71. Hättig, C.; Köhn, A. J. Chem. Phys. 2002, 117, 6939-6951.
72. Hättig, C.; Köhn, A.; Hald, K. J. Chem. Phys. 2002, 116 (6), 5401-5410.
73. Albrecht, A. C. J. Mol. Spectrosc. 1961, 6, 84-108.
74. Radziszewski, J. G.; Michl, J. J. Am. Chem. Soc. 1986, 108, 3289-3297.
75. Thulstrup, E. W.; Michl, J. J. Am. Chem. Soc. 1982, 104, 55945604.
76. Michl, J.; Thulstrup, E. W. Acc. Chem. Res. 1987, 20, 192-199.
77. Platt, J. R. J. Chem. Phys. 1949, 17, 484-495.
78. Moffitt, W. J. Chem. Phys. 1954, 320-333, 1820-1829.
79. Michl, J. Tetrahedron 1984, 40, 3845-3934.
80. Michl, J. J. Am. Chem. Soc. 1978, 100, 6801-6811, 6812-6818, 6819-6827.
81. Havias, Z.; Michl, J. Unpublished results.
82. Nelsen, S. F.; Weaver, M. N.; Yamazaki, D.; Komatsu, K.; Rathore, R.; Bally, T. J. Phys. Chem. A 2007, 111, 1667-1676.