Accurate calculated optical properties of substituted quaterphenylene nanofibers

Journal of Physical Chemistry A

Volumn 114, Issue 1, 2010, Pages 474-480

  Finnerty, Justin J ^a   Koch, Rainer ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACCURATE PREDICTION; B3LYP/6-31G; BASIS SETS; DENSITY-FUNCTIONAL METHODS; EMISSION ENERGIES; EXPERIMENTAL DATA; HF/6-31G; LINEAR SCALING; NONLOCAL; RELATED SYSTEMS; RELAXATION ENERGIES; SECOND ORDERS; SINGLE MOLECULE;

NANOFIBERS; OPTICAL CORRELATION;

OPTICAL PROPERTIES;

NANOFIBER; POLYMER; POLYPHENYLENE SULFIDE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; COMPUTER SIMULATION; OPTICS;

COMPUTER SIMULATION; MODELS, CHEMICAL; NANOFIBERS; OPTICS AND PHOTONICS; POLYMERS;

EID: 75249093486     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp906233d     Document Type: Article

References (75)

1. Carroll, R. L.; Gorman, C. B. Angew. Chem. 2002, 114, 4556-4579.
2. Carroll, R. L.; Gorman, C. B. Angew. Chem., Int. Ed. 2002, 41, 4378-4400.
3. Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem. 1998, 110, 416-443.
4. Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem., Int. Ed. 1998, 37, 402-428.
5. Forrest, S. R. Nature 2004, 428, 911-918.
6. Some recent books: Müllen, K.; Wegner, G. Electronic Materials: The Oligomer Approach; Wiley-VCH: Weinheim, 1998.
7. Fichou, D. Handbook of Oligo- and Polythiophenes; Wiley-VCH: Weinheim, 1999.
8. Nalva, H. S. Handbook of Advanced Electronic and Photonic Materials and Devices; Academic Press: San Diego, CA, 2000.
9. Müllen, K.; Scherf, U. Organic Light Emitting Devices-Synthesis, Properties and Applications; Wiley-VCH:Weinheim, 2006.
10. Klauk, H. Organic Electronics-An Industrial Perspective; Wiley VCH: Weinheim, 2006.
11. Schenning, A. P. H. J.; Meijer, E. W. Chem. Commun. 2005, 3245-3258.
12. Special issue on nanowires: Adv. Mater. 2003, 15, 341-468.
13. De Cola, L. Top. Curr. Chem. 2005, 257.
14. A recent review: Hurst, S. J.; Payne, E. K.; Qin, L.; Mirkin, C. A. Angew. Chem. 2006, 118, 2738-2759.
15. Hurst, S. J.; Payne, E. K.; Qin, L.; Mirkin, C. A. Angew. Chem., Int. Ed. 2006, 45, 2672-2692.
16. Schwab, P. F. H.; Levin, M. D.; Michl, J. Chem. Rev. 1999, 99, 1863-1933.
17. Schwab, P. F. H.; Smith, J. R.; Michl, J. Chem. Rev. 2005, 105, 1197-1279.
18. Ziegler, G. In Handbook of Organic Conductive Molecules and Polymers; Nalwa, H. S., Ed.; Wiley: New York, 1997; Vol. 3, Chapter 13.
19. Krause, B.; Dürr, A. C.; Ritley, K.; Schreiber, F.; Dosch, H.; Smilgies, D. Phys. Rev.B 2002, 66, 235404.
20. Würthner, F. Chem. Commun. 2004, 1564-1579.
21. Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891-4945.
22. James, D. K.; Tour, J. M. Top. Curr. Chem. 2005, 257, 33-62.
23. Resel, R. Thin Film Solids 2003, 433, 1-11.
24. Balzer, F.; Rubahn, H.-G. Adv. Funct. Mater. 2005, 14, 17-24.
25. Balzer, F.; Rubahn, H.-G. PhiuZ 2005, 36, 36-43.
26. Witte, G.; Woell, C. J. Mater. Res. 2004, 19, 1889-1916.
27. Hertel, D.; Müller, C. D.; Meerholz, K. ChiuZ 2005, 39, 336-347.
28. Schiek, M.; Al-Shamery, K.; Lützen, A. Synthesis 2007, 61,3-621. To get a more general overview of other synthetic methods that were applied for the synthesis of oligo-p-phenylenes, we refer to the references cited therein.
29. Schiek, M.; Lützen, A.; Koch, R.; Al-Shamery, K.; Balzer, F.; Rubahn, H.-G. Appl. Phys. Lett. 2005, 86, 153107.
30. Schiek, M.; Lützen, A.; Al-Shamery, K.; Balzer, F.; Rubahn, H. G. Surf. Sci. 2006, 600, 4030-4033.
31. Schiek, M.; Lützen, A.; Al-Shamery, K.; Balzer, F.; Rubahn, H. G. Cryst. Growth Des. 2007, 7, 229-233.
32. Banerjee, M.; Shukla, R.; Rathore, R. J. Am. Chem. Soc. 2009, 131, 1780-1786.
33. Quochi, F.; Cordella, F.; Orrì, R.; Communal, J. E.; Verzeroli, P.; Mura, A.; Bongiovanni, G.; Andreev, A.; Sitter, H.; Sariciftci, N. S. Appl. Phys. Lett. 2004, 84, 4454-4456.
34. Quochi, F.; Cordella, F.; Mura, A.; Bongiovanni, G.; Balzer, F.; Rubahn, H.-G. J. Phys. Chem. B 2005, 109, 21690-21693.
35. Quochi, F.; Cordella, F.; Mura, A.; Bongiovanni, G.; Balzer, F.; Rubahn, H.-G. Appl. Phys. Lett. 2006, 88, 041106.
36. Yanagi, H.; Morikawa, T. Appl. Phys. Lett. 1999, 75, 187-189.
37. Balzer, F.; Bordo, V. G.; Simonsen, A. C.; Rubahn, H.-G. Appl. Phys. Lett. 2003, 82, 10-13.
38. Balzer, F.; Bordo, V. G.; Simonsen, A. C.; Rubahn, H.-G. Phys. Rev.B 2003, 67, 115408.
39. Koch, R.; Finnerty, J. J.; Bruhn, T. J. Phys. Org. Chem. 2008, 21, 954-962.
40. Brewer, J.; Schiek, M.; Wallmann, I.; Rubahn, H.-G. Opt. Commun. 2008, 281, 3892-3896.
41. Adamo, C.; Scuseria, G. E.; Barone, V. J. Chem. Phys. 1999, 111, 2889-2899.
42. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664-675.
43. Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811-4815.
44. Schwabe, T.; Grimme, S. Phys. Chem. Chem. Phys. 2006, 8, 4398-4401.
45. Handy, N. C.; Cohen, A. J. Mol. Phys. 2001, 99, 403-412.
46. Ridley, J. E.; Zerner, M. C. Theor. Chim. Acta 1973, 32, 111-134.
47. Zerner, M. C. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH Publishing: New York, 1991; Vol2, 313-366.
48. 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 Rev. C2; Gaussian, Inc.: Pittsburgh, PA, 2004.
49. Wallmann, I.; Schiek, M.; Koch, R.; Lützen, A. Synthesis 2008, 2446-2450.
50. Vögtle, F.; Kadei, K. Chem. Ber. 1991, 124, 903-907.
51. Keegstra, M. A.; De Feyter, S.; De Schryver, F. C.; Müllen, K. Angew. Chem. 1996, 108, 830-833.
52. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
53. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev.B 1988, 37, 785-789.
54. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724-728.
55. Casida, M. E. In Recent Advances in Density Functional Methods, Part 1; Chong, D. P., Ed.; World Scientific: Singapore, 1995; Vol. 1.
56. ORCA - An ab initio, DFT and semiempirical SCF-MO package - Version 2.7-00, Neese, F.; University of Bonn, 2009.
57. INDO/S data calculated with both programs generally match, with the following exceptions: Gaussian does not contain parameters for halogen atoms and the data for nitro group containing molecules differ by about 30 nm with Orca data being red shifted. In the latter case, the Gaussian numbers are used because they agree better with data calculated with other programs.
58. Foresman, J. B.; Head-Gordon, M.; Pople, J. A.; Frisch, M. J. J. Phys. Chem. 1992, 96, 135.
59. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
60. Francl, M. M.; Pietro, W. L.; Hehre, W. L.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654-3665.
61. INDO/S is parametrized to fit experimental solution data so the use of an additional solvent field is not necessary.
62. Saitoh, H.; Saito, K.; Yamamura, Y.; Matsuymam, H.; Kiuchi, K.; Ikemato, I. Solid State Commun. 1994, 91, 89-92.
63. Baudour, J. L. Acta Crystallogr., Sect. B 1991, B47, 935-949.
64. Baudour, J. L.; Delugeard, Y.; Rivet, P. Acta Crystallogr., Sect. B 1978, B34, 625-628.
65. Baudour, J. L.; Cailleau, H.; Yelon, W. B. Acta Crystallogr., Sect. B 1977, B33, 1773-1780.
66. Delugeard, Y.; Desuche, J.; Baudour, J. L. Acta Crystallogr., Sect. B 1976, B32, 702-705.
67. For a full discussion of β conventions used in experimental and theoretical studies see: Willetts, A.; Rice, J. E.; Burland, D. M.; Shelton, D. P. J. Chem. Phys. 1992, 97, 7590-7599.
68. For a detailed study on the media effect see: Cammi, R.; Mennucci, B.; Tomasi, J. J. Am. Chem. Soc. 1998, 120, 8834-8847.
69. Jacquemin, D.; Assfeld, X.; Perpete, E. A. J. Mol. Struct. (THEOCHEM) 2004, 710, 13-17.
70. Draper, N. R.; Smith, H. Applied Regression Analysis, 2nd ed.; Wiley: New York, 1981; pp 97-98 and 141-151.
71. Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Phys. Chem. A 2002, 106, 10596-10605.
72. Guillaume, M.; Champagne, B.; Zutterman, F. J. Phys. Chem. A 2006, 110, 13007-13013.
73. The fact of a solely statistical phenomenon of lowering SSDs can be concluded from the values of the fitting parameters which do not reflect the correlation between experimental and calculated data: intercepts of 400 are chemically not meaningful, also a slope of 0.2 is nowhere near any chemical relevance.
74. Schiek, M. Ph.D. thesis, Uni Oldenburg, 2007.
75. Zhao, C.; Sakuda, E.; Wakamiya, A.; Yamaguchi, S. Chem. Eur. J. 2009, 15, 10603-10612 (http://dx.doi.org/10.1002/chem.200900864).