Paracyclophanes as model compounds for strongly interacting π-systems, part 3: Influence of the substitution pattern on photoabsorption properties

Journal of Physical Chemistry A

Volumn 115, Issue 15, 2011, Pages 3583-3591

  Pfister, Johannes ^a   Schon, Christof ^a   Roth, Wolfgang ^b   Kaiser, Conrad ^a   Lambert, Christoph ^a   Gruss, Katrin ^a   Braunschweig, Holger ^a   Fischer, Ingo ^a   Fink, Reinhold F ^a   Engels, Bernd ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

[2.2]PARACYCLOPHANE; ADIABATIC EXCITATION ENERGIES; AROMATIC MOLECULES; B3LYP METHOD; BREATHING MODES; COUPLED CLUSTERS; EXPERIMENTAL VALUES; FIRST EXCITED STATE; FRANCK-CONDON SIMULATIONS; FREE JETS; IN-LINE; MODEL COMPOUND; PERTURBATION METHOD; PHOTO-ABSORPTION PROPERTY; PROPAGATION METHOD; QUANTUM CHEMICAL CALCULATIONS; RESONANCE-ENHANCED MULTIPHOTON IONIZATION; SECOND ORDERS; SHIFT-AND; STRUCTURAL CHANGE; STRUCTURAL PARAMETER; SUBSTITUTION PATTERNS; TIME-DEPENDENT DENSITY; VIBRATION ENERGIES; X-RAY STRUCTURE; ZERO-POINT;

BENZENE; DENSITY FUNCTIONAL THEORY; ELECTRIC EXCITATION; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRONIC STRUCTURE; PERTURBATION TECHNIQUES; PHENOLS; PHOTOIONIZATION; QUANTUM CHEMISTRY; X RAY CRYSTALLOGRAPHY;

EXCITED STATES;

AROMATIC HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PHOTOCHEMISTRY; QUANTUM THEORY; SYNTHESIS;

HYDROCARBONS, AROMATIC; MODELS, MOLECULAR; PHOTOCHEMICAL PROCESSES; QUANTUM THEORY;

EID: 79954605861     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp200823q     Document Type: Article

References (75)

1. Valentini, L.; Marrocchi, A.; Seri, M.; Mengoni, F.; Meloni, F.; Taticchi, A.; Kenny, J. M. Thin Solid Films 2008, 516, 7193
2. Hopf, H. Angew. Chem., Int. Ed. 2008, 47, 9808
3. Amthor, S.; Lambert, C.; Dümmler, S.; Fischer, I.; Schelter, J. J. Phys. Chem. A 2006, 110, 5204
4. Hu, W.; Gompf, B.; Pflaum, J.; Schweitzer, D.; Dressel, M. Appl. Phys. Lett. 2004, 84, 4720
5. Goldhaber-Gordon, D.; Montemerlo, M. S.; Love, J. C.; Opiteck, G. J.; Ellenbogen, J. C. Proc. IEEE 1997, 85, 521
6. Sheats, J. R.; Barbara, P. F. Acc. Chem. Res. 1999, 32, 191
7. Nespurek, S.; Sworakowski, J. IEEE Eng. Med. Biol. 1994, 13, 45
8. Joachim, C.; Gimzewski, J. K. Chem. Phys. Lett. 1997, 265, 353
9. Birge, R. R. Am. Sci. 1994, 82, 348
10. Cradall, B. C. L. J. Nanotechnology: Research and Perspectives; MIT Press: Cambridge, 1992.
11. Fox, M. A. Acc. Chem. Res. 1999, 32, 201
12. Klauk, H. Chem. Soc. Rev. 2010, 39, 2643
13. Brooks, J. S. Chem. Soc. Rev. 2010, 39, 2667
14. Katan, C.; Terenziani, F.; Mongin, O.; Werts, M. H. V.; Porres, L.; Pons, T.; Mertz, J.; Tretiak, S.; Blanchard-Desce, M. J. Phys. Chem. A 2005, 109, 3024
15. Masumov, A.; Tretiak, S.; Hong, J. W.; Liu, B.; Bazan, G. C. J. Chem. Phys. 2005, 122, 224505
16. Neelakandan, P. P.; Ramaiah, D. Angew. Chem., Int. Ed. 2008, 47, 8407
17. Kahnt, A.; Guldi, D. M.; Escosura, A. d. l.; Martin-Diaz, M. V.; Torres, T. J. Mater. Chem. 2008, 18, 77
18. Seferos, D. S.; Trammell, S. A.; Bazan, G. C.; Kushmerick, J. G. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 8821
19. Bazan, G. C. J. Org. Chem. 2007, 72, 8615
20. Morisaki, Y.; Chujo, Y. Angew. Chem., Int. Ed. 2006, 45, 6430
21. Seferos, D. S.; Szuchmacher Blum, A.; Kushmerick, J. G.; Bazan, G. C. J. Am. Chem. Soc. 2006, 128, 11260
22. Brown, C. J.; Farthing, A. C. Nature 1949, 164, 915
23. Vögtle, F. Cyclophane Chemistry; Wiley-VCH: New York, 1993.
24. Takemura, H. Cyclophane Chemistry for the 21st Century; Research-Signpost: Trivan-Drum, 2002.
25. Hopf, R. G. Modern Cyclophane Chemistry; Wiley-VCH: Weinheim, 2004.
26. Vorontsova, N. V.; Bystrova, G. S.; Antonov, D. Y.; Vologzhanina, A. V.; Godovikov, I. A.; Il'in, M. M. Tetrahedron: Asymmetry 2010, 21, 731
27. Friedmann, C. J.; Ay, S.; Brase, S. J. Org. Chem. 2010, 75, 4612
28. Zhang, T. Z.; Dai, L. X.; Hou, X. L. Tetrahedron: Asymmetry 2007, 18, 251
29. Antonov, D. Y.; Rozenberg, V. I.; Danilova, T. I.; Starikova, Z. A.; Hopf, H. Eur. J. Org. Chem. 2008, 1038
30. Schon, C.; Roth, W.; Fischer, I.; Pfister, J.; Fink, R. F.; Engels, B. submitted 2010.
31. Schon, C.; Roth, W.; Fischer, I.; Pfister, J.; Kaiser, C.; Fink, R. F.; Engels, B. Phys. Chem. Chem. Phys. 2010, 12, 9339
32. Zimmermann, R. " REMPI-Spectroscopy of organic molecules with unusual electronic properties: Biphenylene and [2,2]-Paracyclophane "; Resonance ionization spectroscopy 1996: Eighth international symposium, 1997.
33. Grimme, S. Chem. Eur. J. 2004, 10, 3423
34. Grimme, S. J. Chem. Phys. 2003, 118, 9095
35. Hellweg, A.; Grun, S. A.; Hättig, C. Phys. Chem. Chem. Phys. 2008, 10, 4119
36. Christiansen, O.; Stanton, J. F.; Gauss, J. J. Chem. Phys. 1998, 108, 3987
37. Schemmel, D.; Schutz, M. J. Chem. Phys. 2007, 127, 174304
38. Schemmel, D.; Schutz, M. J. Chem. Phys. 2008, 129, 034301
39. Reich, H. J.; Cram, D. J. J. Am. Chem. Soc. 1969, 91, 3527
40. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112
41. Christiansen, O.; Koch, H.; Jørgensen, P. Chem. Phys. Lett. 1995, 243, 409
42. Hättig, C.; Kohn, A. J. Chem. Phys. 2002, 117, 6939
43. Hättig, C.; Weigend, F. J. Chem. Phys. 2000, 113, 5154
44. Ahlrichs, R.; Böcker, S.; Ehrig, M.; Eichkorn, K.; Elliott, S.; Haase, F.; Häser, M.; Horn, H.; Huber, C.; Huniar, U.; Kattannek, M.; Kölmel, C.; Kollwitz, M.; Ochsenfeld, C.; Öhm, H.; Schäfer, A.; Schneider, U.; Treutler, O.; von Arnim, M.; Weigend, F.; Weis, P.; Weiss, H. TURBOMOLE 5.10; version 5.10; University of Karlsruhe: Karlsruhe, Germany, 2008.
45. Schafer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829
46. Weigend, F.; Häser, M.; Patzelt, H.; Ahlrichs, R. Chem. Phys. Lett. 1998, 294, 143
47. Eichkorn, K.; Treutler, O.; Ohm, H.; Haser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 242, 652
48. Vahtras, O.; Almlof, J.; Feyereisen, M. W. Chem. Phys. Lett. 1993, 213, 514
49. Schafer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571
50. Sinha, P.; Boesch, S. E.; Gu, C. M.; Wheeler, R. A.; Wilson, A. K. J. Phys. Chem. A 2004, 108, 9213
51. Pople, J. A.; Scott, A. P.; Wong, M. W.; Radom, L. Isr. J. Chem. 1993, 33, 345
52. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502
53. Duschinsky, F. Acta Physiochim. USSR 1937, 551
54. Malagoli, M.; Coropceanu, V.; da Silva, D. A.; Bredas, J. L. J. Chem. Phys. 2004, 120, 7490
55. Ballhausen, C. J. Molecular Electronic Structures of Transition Metal Complexes; McGraw-Hill: New York, 1979.
56. Mulliken, R. S. J. Chem. Phys. 1955, 23, 1997
57. Schutte, C. J. H.; Bertie, J. E.; Bunker, P. R.; Hougen, J. T.; Mills, I. M.; Watson, J. K. G.; Winnewisser, B. P. Pure Appl. Chem. 1997, 69, 1641
58. Henseler, D.; Hohlneicher, G. J. Phys. Chem. A 1999, 103, 1160
59. Lyssenko, K. A.; Antipin, M. Y.; Antonov, D. Y. ChemPhysChem 2003, 4, 817
60. Walden, S. E.; Glatzhofer, D. T. J. Phys. Chem. A 1999, 103, 1162
61. Hope, H.; Bernstein, J.; Trueblood, K. N. Acta Crystallogr. B 1972, 28, 1733
62. Cram, D. J.; Cram, J. M. Acc. Chem. Res. 1971, 4, 204
63. Jones, P. G.; Dix, I.; Hopf, H. Acta Crystallogr. C 2007, 63, o468
64. Jones, P. G.; Hillmer, J.; Hopf, H. Acta Crystallogr. C 2002, 58, o301
65. Starikova, Z. A.; Fedyanin, I. V.; Antipin, M. Y. Russ. Chem. Bull. 2004, 53, 1779
66. Wilson, W. B.; Decius, J. C.; Cross, P. C. Molecular Vibrations: The Theory of Infrared and Raman Vibrational Spectra; Dover Publications, Inc.: Mineola, NY, 1980.
67. Lonsdale, K.; Milledge, H. J.; Rao, K. V. K. Proc. R. Soc. Longon, Ser. A 1960, A 255, 82
68. Nagel, M.; Allmann, R.; Eltamany, S. H.; Hopf, H. Chem. Ber. 1982, 115, 3203
69. Goumans, T. P.; Ehlers, A. W.; Lammertsma, K.; Wurthwein, E. U.; Grimme, S. Chemistry 2004, 10, 6468
70. Grimme, S. J. Phys. Chem. A 2005, 109, 3067
71. Yang, L.; Caprasecca, S.; Mennucci, B.; Jang, S. J. Am. Chem. Soc. 2010, 132, 16911
72. Sinnokrot, M. O.; Sherrill, C. D. J. Phys. Chem. A 2006, 110, 10656
73. Stephenson, T. A.; Radloff, P. L.; Rice, S. A. J. Chem. Phys. 1984, 81, 1060
74. Berden, G.; Meerts, W. L.; Schmitt, M.; Kleinermanns, K. J. Chem. Phys. 1996, 104, 972
75. Shen, T. L.; Jackson, J. E.; Yeh, J. H.; Nocera, D. G.; Leroi, G. E. Chem. Phys. Lett. 1992, 191, 149