Vibrational raman optical activity of π-conjugated helical systems: Hexahelicene and heterohelicenes

Journal of Computational Chemistry

Volumn 30, Issue 8, 2009, Pages 1261-1278

  Liégeois, Vincent ^a   Champagne, Benoît ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

Chirality; Helicenes; Raman; TDHF; Vibrational spectra; VROA

Indexed keywords

BASIS SETS; C ATOMS; CARBON SKELETON; CHIROOPTICAL PROPERTIES; CONJUGATED STRUCTURES; HELICAL CONFORMATION; HELICAL SYSTEMS; HELICENE; HELICENES; HELICITY; HETEROATOM; HETEROATOMS; HETEROHELICENES; NORMAL MODES; RAMAN; SPECIAL CLASS; SPECTRAL PATTERNS; TDHF; VIBRATIONAL MODES; VIBRATIONAL RAMAN OPTICAL ACTIVITIES; VIBRATIONAL SIGNATURE; VROA;

ATOMS; CHIRALITY; ELECTRONIC PROPERTIES; ENANTIOMERS; MOLECULAR SPECTROSCOPY; NITROGEN COMPOUNDS; OPTICAL MATERIALS; STEREOCHEMISTRY; VIBRATIONAL SPECTRA;

ORGANIC POLYMERS;

FURAN DERIVATIVE; HELICENES; POLYCYCLIC HYDROCARBON; PYRROLE DERIVATIVE; TETRATHIA(7) HELICENE; TETRATHIA(7)-HELICENE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; COMPUTER SIMULATION; RAMAN SPECTROMETRY; VIBRATION;

COMPUTER SIMULATION; FURANS; MODELS, CHEMICAL; POLYCYCLIC COMPOUNDS; PYRROLES; SPECTRUM ANALYSIS, RAMAN; VIBRATION;

EID: 66449098748     PISSN: 01928651     EISSN: 1096987X     Source Type: Journal    
DOI: 10.1002/jcc.21151     Document Type: Article

References (71)

1. Martin, R. H. Angew Chem Int Ed 1974, 13, 649.
2. Autschbach, J.; Patchkovskii, S.; Ziegler, T.; van Gisbergen, S. J. A.; Baerends, E. J. J Chem Phys 2002, 117, 581.
3. Furche, F.; Ahlrichs, R.; Wacksmann, C.; Weber, E.; Sobanski, A.; Vogtle, F.; Grimme, S. J Am Chem Soc 2000, 122, 1717.
4. Autschbach, J.; Ziegler, T.; van Gisbergen, S. J. A.; Baerends, E. J. J Chem Phys 2002, 116, 6930.
5. Spassova, M.; Asselberghs, I.; Verbiest, T.; Clays, K.; Botek, E.; Champagne, B. Chem Phys Lett 2007, 439, 213.
6. Botek, E.; Champagne, B. J Chem Phys 2007, 127, 204101.
7. erbiest, T.; Elshocht, S. V.; Kauranen, M.; Hellemans, L.; Snauwaert, J.; Nuckolls, C.; Katz, T. J.; Persoons, A. Science 1998, 282, 913.
8. Verbiest, T.; Sioncke, S.; Persoons, A.; Vyklicky, L.; Katz, T. J. Angew Chem Int Ed 2002, 41, 3882.
9. Daul, C. A.; Ciofini, I.; Weber, V. Int J Quantum Chem 2003, 91, 297.
10. Botek, E.; Champagne, B.; Turki, M.; Andre, J. M. J Chem Phys 2004, 120, 2042.
11. Champagne, B.; Andre, J.-M.; Botek, E.; Licandro, E.; Maiorana, S.; Bossi, A.; Clays, K.; Persoons, A. Chem Phys Chem 2004, 5, 1438.
12. Botek, E.; Spassova, M.; Champagne, B.; Asselberghs, I.; Persoons, A.; Clays, K.; Chem Phys Lett 2005, 412, 274.
13. Botek, E.; Spassova, M.; Champagne, B.; Asselberghs, I.; Persoons, A.; Clays, K. Erratum Chem Phys Lett 2006, 417, 282.
14. Bossi, A.; Licandro, E.; Maiorana, S.; Rigamonti, C.; Righetto, E.; Stephenson, G. R.; Spassova, M.; Botek, E.; Champagne, B. J Phys Chem C 2008, 112, 7900.
15. Jansík, B.; Rizzo, A.; Agren, H.; Champagne, B. J Chem Theory Comput 2008, 4, 457.
16. Nicu, V. P.; Neugebauer, J.; Wolff, S. K.; Baerends, E. J. Theor Chem Acc 2008, 119, 245.
17. Hug, W.; Haesler, J.; Kozhushkov, S. I.; de Meijere, A. ChemPhys Chem 2007, 8, 1161.
18. Barron, L. D.; Hecht, L.; Gargaro, A. R.; Hug, W. J Raman Spectrosc 1990, 21, 375.
19. Hug, W. Handbook of Vibrational Spectroscopy; Wiley: Chichester, 2002; Vol. 1, p. 175.
20. Ruud, K.; Helgaker, T.; Bour, P. J Phys Chem A 2002, 106, 7448.
21. Bour, P.; Sychrovsky, V.; Malon, P.; Hanzlikova, J.; Baumruk, V.; Pospisek, J.; Budesinsky, M. J Phys Chem A 2002, 106, 7321.
22. Pecul, M.; Rizzo, A.; Leszczynski, J. J Phys Chem A 2002, 106, 11008.
23. Zuber, G.; Hug, W. Helv Chim Acta 2004, 87, 2208.
24. Barron, L. D.; Hecht, L.; McColl, I. M.; Blanch, E. W. Mol Phys 2004, 102, 731.
25. Zuber, G.; Goldsmith, M.-R.; Beratan, D. N.; Wipf, P. ChemPhys Chem 2005, 6, 595.
26. Reiher, M.; Liégeois, V.; Ruud, K. J Phys Chem A 2005, 109, 7567.
27. Haesler, J.; Schindelholz, I.; Riguet, E.; Bochet, C. G.; Hug, W. Nature 2007, 446, 526.
28. McColl, I. H.; Blanch, E. W.; Gill, A. C.; Rhie, A. G. O.; Ritchie, M. A.; Hecht, L.; Nielsen, K.; Barron, L. D. J Am Chem Soc 2003, 125, 10019.
29. Blanch, E. W.; Gill, A. C.; Rhie, A. G. O.; Hope, J.; Hecht, L.; Nielsen, K.; Barron, L. D. J Mol Biol 2004, 343, 467.
30. McColl, I. H.; Blanch, E. W.; Hecht, L.; Kallenbach, N. R.; Barron, L. D. J Am Chem Soc 2004, 126, 5076.
31. McColl, I. H.; Blanch, E. W.; Hecht, L.; Barron, L. D. J Am Chem Soc 2004, 126, 8181.
32. Zhu, F.; Isaacs, N. W.; Hecht, L.; Barron, L. D. J Am Chem Soc 2005, 127, 6142.
33. Zhu, F.; Isaacs, N. W.; Hecht, L.; Tranter, G. E.; Barron, L. D. Chirality 2006, 18, 103.
34. Kapitan, J.; Baumruk, V.; Bour, P. J Am Chem Soc 2006, 128, 2438.
35. Barron, L.; Zhu, F.; Hecht, L. Vib Spectrosc 2006, 42, 15.
36. Barron, L. D.; Zhu, F.; Hecht, L.; Tranter, G. E.; Isaacs, N. W. J Mol Struct 2007, 834-836, 7.
37. Hobro, A. J.; Rouhi, M.; Blanch, E. W.; Conn, G. L. Nucleic Acid Res 2007,35, 1169.
38. Jalkanen, K. J.; Gale, J. D.; Jalkanen, G. J.; McIntosh, D. F.; El-Azhary, A. A.; Jensen, G. M. Theor Chem Acc 2008, 119, 211.
39. Liegeois, V.; Quinet, O.; Champagne, B. J Chem Phys 2005, 122, 214304.
40. Liegeois, V.; Quinet, O.; Champagne, B. Int J Quantum Chem 2006, 106, 3097.
41. Lamparska, E.; Liegeois, V.; Quinet, O.; Champagne, B. Chem Phys Chem 2006, 7, 2366.
42. Herrmann, C.; Ruud, K.; Reiher, M. Chem Phys Chem 2006, 7, 2189.
43. Herrmann, C.; Ruud, K.; Reiher, M. Chem Phys 2008, 343, 200.
44. Snyder, R. G. J Chem Phys 1967, 47, 1316.
45. Kirtman, B.; Champagne, B.; Andre, J. J Chem Phys 1996, 104, 4125.
46. Liégeois, V.; Ruud, K.; Champagne, B.J Chem Phys 2007,127,204105.
47. Maiorana, S.; Papagni, A.; Licandro, E.; Annunziata, R.; Paravidino, P.; Perdicchia, D.; Giannini, C.; Bencini, M.; Clays, K.; Persoons, A. Tetrahedron 2003, 59, 6481.
48. Baldoli, C.; Bossi, A.; Giannini, C.; Licandro, E.; Maiorana, S.; Perdicchia, D. Synlett p. 1137 (2005).
49. Licandro, E.; Rigamonti, C.; Tocozzelli, M. T.; Monteforte, M.; Baldoli, C.; Giannini, C.; Maiorana, S. Synthesis 2006, 21, 3670.
50. Bossi, A.; Maiorana, S.; Baldoli, C.; Graiff, C.; Tiripicchio, A.; Licandro, E. Eur J Org Chem 2007, 27, 4499.
51. Barron, L. D.; Buckingham, A. D. Mol Phys 1971, 20, 1111.
52. Barron, L. D.; Molecular Light Scattering and Optical Activity; Cambridge University Press: Cambridge, 2004.
53. Buckingham, A. D. Adv Chem Phys 1967, 12, 107.
54. Hug, W. et al. VOAView, a graphical package to interpret vibrational spectra.
55. Fedorovsky, M. Pyvib2, a program for analyzing vibrational motion and vibrational spectra, 2007. Available at: http://pyvib2.sourceforge.net.
56. Fedorovsky, M. Comput Lett 2006, 2, 233.
57. Hug, W. Comput Lett 2006, 2, 251.
58. Hug, W.; Fedorovksy, M. Theor Chem Acc 2008, 119, 113.
59. Komornicki, A.; Fitzgerald, G. J Chem Phys 1993, 98, 1398.
60. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J Chem Phys 1972, 56, 2257.
61. Scott, A. P.; Radom, L. J Phys Chem 1996, 100, 16502.
62. Irikura, K. K.; Johnson, R. D., III; Kacker, R. N. J Phys Chem A 2005, 109, 8430.
63. Zuber, G.; Hug, W. J Phys Chem A 2004, 108, 2108.
64. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J Am Chem Soc 1980, 102, 939.
65. DALTON, a molecular electronic structure program, Release 2.0, 2005. Available at: http://www.kjemi.uio.no/software/dalton/dalton.html.
66. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al- Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision b. 04; Gaussian, Inc.: Wallingford, CT, 2004.
67. London, F. J Phys Radium 1937, 8, 397.
68. Ditchfield, R. J Am Chem Soc 1971, 93, 5287.
69. Liégeois, V.; Champagne, B.; Lazzeretti, P. J Chem Phys 2008, 128, 244107.
70. Epstein, S. T. The Variation Method in Quantum Chemistry; Academic Press: New York, 1974.
71. Luber, S.; Herrmann, C.; Reiher, M. J Phys Chem B 2008, 112, 2218.