Through versus cross electron delocalization in polytriacetylene oligomers: A computational analysis

ChemPhysChem

Volumn 6, Issue 3, 2005, Pages 511-519

  Bruschi, Maurizio ^a,b   Giuffreda, Maria Grazia ^a   Lüthi, Hans Peter ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF MILANO BICOCCA   (Italy)

Author keywords

Ab initio calculations; Conjugation; Density functional calculations; Electron delocalization; Electronic structure

Indexed keywords

CALCULATIONS; CARBON; DENSITY FUNCTIONAL THEORY; ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; ELECTRONS; IONIZATION POTENTIAL; NONLINEAR OPTICS; OPTICAL PROPERTIES; REDUCTION;

AB INITIO CALCULATIONS; COMPUTATIONAL ANALYSIS; CONJUGATION; EFFECTIVE CONJUGATION LENGTH; ELECTRON DELOCALIZATION; MOLECULAR GEOMETRIES; NON-LINEAR OPTICAL PROPERTIES; THEORETICAL INVESTIGATIONS;

OLIGOMERS;

ACETYLENE DERIVATIVE; ANION; CARBON; CATION; OLIGOMER;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON; ENERGY; GEOMETRY; IONIZATION; OPTICS;

EID: 16644371116     PISSN: 14394235     EISSN: None     Source Type: Journal    
DOI: 10.1002/cphc.200400202     Document Type: Article

References (73)

1. a) Electronic Properties of Conjugated Polymers III: Basic Models and Applications (Eds.: H. Kuzmani, M. Mehring, S. Roth), Springer, Berlin 1989;
2. b) J. S. Miller, Adv. Mater. 1993, 5, 671-676;
3. c) Conjugated Polymers and Related Materials. The Interconnection of Chemical and Electronic Structure (Eds.: W. R. Salaneck, I. Lundström B. Ränby), Oxford University Press, Oxford, 1993;
4. d) Handbook of Organic Conductive Molecules and Polymers, Vol. 1-4 (Ed.: H. S. Nalwa), Wiley, Chinchester, 1997;
5. e) Handbook of Conducting Polymers, 2nd ed. (Eds.: T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds), Dekker, New York 1998;
6. f) M. Liphardt, A. Goonesekera, B. E. Jones, S. Ducharme, J. M. Takacs, L. Zhang, Science 1994, 263, 367-369;
7. g) N. C. Greenham, S. C. Moratti, D. D. C. Bradley, R. H. Friend, A. B. Holmes, Nature 1993, 365, 628-630;
8. h) A. Buckley, Adv. Mater. 1992, 4, 153-158;
9. i) H. S. Nalwa, Adv. Mater. 1993, 5, 341-358;
10. j) S. Moller, C. Perlov, W. Jackson, C. Taussing, S. R. Forrest, Nature 2003, 426, 166-169;
11. k) M. Gratzel, Nature 2001, 414, 338-344.
12. a) D. L. Pearson, J. S. Schumm, J. M. Tour, Macromolecules 1994, 27, 2348-2350;
13. b) P. Seta, E. Bienvenue, Mol. Electron. Mol. Electron. Devices 1994, 3, 59-78;
14. c) L. Jones II, D. L. Pearson, J. S. Schumm, J. M. Tour, Pure Appl. Chem. 1996, 68, 145-148;
15. d) J. M. Tour, Chem. Rev. 1996, 96, 537-553;
16. e) M. D. Ward, Chem. Ind. 1996, 15, 568-573;
17. f) T. Bartik, B. Bartik, M. Brady, R. Dembinski, J. A. Gladsyz, Angew. Chem. 1996, 108, 467-469; Angew. Chem. Int. Ed. Engl. 1996, 35, 414-417;
18. f) T. Bartik, B. Bartik, M. Brady, R. Dembinski, J. A. Gladsyz, Angew. Chem. 1996, 108, 467-469; Angew. Chem. Int. Ed. Engl. 1996, 35, 414-417;
19. g) J. S. Schumm, D. L. Pearson, J. M. Tour, Angew. Chem. 1994, 106, 1445-1448, Angew. Chem. Int. Ed. Engl. 1994, 33, 1360-1363;
20. g) J. S. Schumm, D. L. Pearson, J. M. Tour, Angew. Chem. 1994, 106, 1445-1448, Angew. Chem. Int. Ed. Engl. 1994, 33, 1360-1363;
21. h) R. H. Grubbs, D. Kratz, Chem. Ber. 1993, 126, 149-157.
22. a) M. Schreiber, J. Anthony, F. Diederich, M. E. Spahr, R. Nesper, M. Hubrich, F. Bommeli, L. Degiorgi, P. Wachter, P. Kaatz, C. Bosshard, P. Günter, M. Colussi, U. W. Suter, C. Boudon, J.-P. Gisselbrecht, M. Gross, Adv. Mater. 1994, 6, 786-790;
23. b) M. Schreiber, R. R. Tykwinski, F. Diederich, R. Spreiter, U. Gubler, C. Bosshard, I. Poberaj, P. Günter, C. Boudon, J.-P. Gisselbrecht, M. Gross, U. Jonas, H. Ringsdorf, Adv. Mater. 1997, 9, 339-343;
24. c) R. E. Martin, U. Gubler, J. Cornil, M. Y. Balakina, C. Boudon, C. Bosshard, J.-P. Gisselbrecht, F. Diederich, P. Günter, M. Gross, J-L. Brédas, Chem. Eur. J. 2000, 6, 3622-3634;
25. d) U. Gubler, C. Bosshard, P. Günter, M. Y. Balakina, J. Cornil, J-L Brédas, R. E. Martin, F. Diederich, Opt. Lett. 1999, 24, 1599-1601;
26. e) R. E. Martin, T. Mäder, F. Diederich, Angew. Chem. 1999, 111, 834-838; Angew. Chem. Int. Ed. 1999, 38, 817-822;
27. e) R. E. Martin, T. Mäder, F. Diederich, Angew. Chem. 1999, 111, 834-838; Angew. Chem. Int. Ed. 1999, 38, 817-822;
28. f) R. E. Martin, F. Diederich, Angew. Chem. 1999, 111, 1440-1469; Angew. Chem. Int. Ed. 1999, 38, 1350-1377.
29. f) R. E. Martin, F. Diederich, Angew. Chem. 1999, 111, 1440-1469; Angew. Chem. Int. Ed. 1999, 38, 1350-1377.
30. a) A. M. Boldi, J. Anthony, V. Gramlich, C. B. Knobler, C. Boudon, J.-P. Gisselbrecht, M. Gross, F. Diederich, Helv. Chim. Acta 1995, 78, 779-796;
31. b) E. Burri, F. Diederich, M. B. Nielsen, Helv. Chim. Acta 2001, 84, 2169-2182;
32. c) R. R. Tykwinski, Y. Zhao, Synlett 2002, 12, 1939-1953;
33. d) Y. Zhao, R. McDonald, R. R. Tykwinski, Chem. Commun. 2000, 1, 77-78;
34. e) Y. Zhao, K. Campbell, R. R. Tykwinski, J. Org. Chem. 2002, 67, 2805-2812.
35. M. Bruschi, M. G. Giuffreda, H. P. Lüthi, Chem. Eur. J. 2002, 8, 4216-4227.
36. M. G. Giuffreda, M. Bruschi, H. P. Lüthi, Chem. Eur. J. 2004, 10, 5671-5680.
37. a) A. J. Heeger, S. Kivelson, J. R. Schrieffer, W.-P. Su, Rev. Mod. Phys. 1988, 60, 781-850;
38. b) M. Kertesz, Adv. Quantum Chem. 1982, 15, 161-214.
39. R. Peierls in Quantum Theory of Solids, Oxford University Press, Oxford, 1954.
40. A. A. Ovchinnikov, I. I. Ukrainskii, G. F. Kvenstel, Usp. Fiz. Nauk. 1972, 108, 81-90.
41. C. H. Choi, M. Kertesz, A. Karpfen, J. Chem. Phys. 1997, 107, 6712-6721.
42. C. H. Choi, M. Kertesz, J. Chem. Phys. 1998, 108, 6681-6688.
43. S. Suhai, Phys. Rev. B 1995, 51, 16553-16557.
44. The geometrical parameters of the PTA and iso-PTA oligomers up to the nonamer are given as Supporting Information.
45. The single-double and single-triple BLAs for PTA of infinite chain length are extrapolated using the function a/[1 + b*exp(-c/N)] as reported in ref. [19a].
46. 26) and we calculated the BLAs (unpublished results).
47. correl is independent of the alternation parameter ΔR. The two energy gaps were taken from the B3LYP/6-31G(d,p)//B3LYP/6-31G(d,p) and BLYP/6-31G(d,p)//BLYP/6-31G(d,p) levels of theory (see also refs. [10] and [11]).
48. The geometrical parameters of the PTA and iso-PTA anions and cations up to the nonamer are given as Supporting Information.
49. M. Klokkenburg, M. Lutz, A. L. Spek, J. H. van der Maas, C. A. van Walree, Chem. Eur. J. 2003, 9, 3544-3554.
50. a) A. D. Bacon, M. C. Zerner, Theor. Chim. Acta 1979, 53, 21-54;
51. b) M. C. Zerner in Metal-Ligand Interactions, Kluwer Academic Publishers, Dordrecht, The Netherlands, 1996, p. 493;
52. c) M. C. Zerner, G. H. Loew, R. F. Kirchner; U. T. Mueller-Westerhoff, J. Am. Chem. Soc. 1980, 102, 589-599;
53. d) J. C. Culberson, P. Knappe, N. Rösch, M. C. Zerner, Theor. Chim. Acta 1987, 71, 21-39;
54. e) J. Ridley, M. C. Zerner, Theor. Chim. Acta 1973, 32, 111-131;
55. f) J. Ridley, M. C. Zerner, Theor. Chim. Acta 1976, 42, 223-236;
56. g) W. P. Anderson, T. Cundari, R. S. Drago, M. C. Zerner, Inorg. Chem. 1990, 29, 1-3;
57. h) W. P. Anderson, T. Cundari, M. C. Zerner, Int. J. Quantum Chem. 1991, 39, 31-45.
58. max values calculated at the ZINDO level are overestimated by about 30 nm, whereas at the BHandHLYP level they are underestimated by about 20 nm.
59. W. J. Hehre, R. Ditchfield, J. A. Pople, J. Chem. Phys. 1972, 56, 2257-2261.
60. a) A. D. Becke, J. Chem. Phys. 1992, 96, 2155-2160;
61. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652;
62. c) P. J. Stevens, F. J. Devlin, C. F. Chablowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.
63. a) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3104;
64. b) A. D. Becke, J. Chem. Phys. 1993, 98, 1372-1377.
65. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
66. J. C. Rienstra-Kiracofe, G. S. Tschumper, H. F. Schaefer, Chem. Rev. 2002, 102, 231-282.
67. a) R. E. Stratmann, G. E. Scuseria, M. J. Frisch, J. Chem. Phys. 1998, 109, 8218-8224;
68. b) R. Bauernschmitt, R. Ahlrichs, Chem. Phys. Lett. 1996, 256, 454-464;
69. c) M. E. Casida, C. Jamorski, K. C. Casida, D. R. Salahub, J. Chem. Phys. 1998, 108, 4439-4449.
70. H. A. Kurtz, J. J. P. Steward K. M. Dieter, J. Comput. Chem. 1990, 11, 82-87.
71. M. J. S. Dewar, W. Thiel, J. Am. Chem. Soc. 1977, 99, 4899-4907.
72. Gaussian 98 (Revision A.7), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.
73. MOPAC2000, J. J. Stewart, Fujitsu Limited, Tokyo, Japan, 1999.