Electron delocalization in linearly π-conjugated systems: A concept for quantitative analysis

Chemistry - A European Journal

Volumn 10, Issue 22, 2004, Pages 5671-5680

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

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF MILANO BICOCCA   (Italy)

Author keywords

Conjugation; Delocalization energy; Density functional calculations; Donor acceptor systems; Local properties

Indexed keywords

COMPUTATIONAL METHODS; MOLECULES; ORGANIC CHEMICALS; SUBSTITUTION REACTIONS;

CONJUGATION PATHS; DELOCALIZATION ENERGIES; INTERACTION ENERGIES; NATURAL BOND ORBITALS (NBO);

ELECTRONS;

ANALYTIC METHOD; ARTICLE; CHROMATOPHORE; CONJUGATION; DENSITY FUNCTIONAL THEORY; DERIVATIZATION; ELECTRON TRANSPORT; LINEAR SYSTEM; MOLECULAR INTERACTION; NONLINEAR SYSTEM; QUANTITATIVE ANALYSIS; QUANTITATIVE ASSAY;

EID: 9244243607     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400313     Document Type: Article

References (55)

1. U. H. F. Bunz, Chem. Rev. 2000, 700, 1605-1644.
2. a) Modern Acetylene Chemistry (Eds.: P. J. Stang, F. Diederich), VCH, Weinheim 1995;
3. b) Carbon Rich Compounds II, Vol. 201 (Ed.: A. de Meijere), Springer, Berlin 1999.
4. a) R. H. Grubbs, D. Kratz, Chem. Ber. 1993, 126, 149-157;
5. b) D. L. Pearson, J. S. Schumm, J. M. Tour, Macromolecules 1994, 27, 2348-2350;
6. c) P. Seta, E. Bienvenue, Mol. Electron. Mol. Electron. Devices 1994, 3, 59-78;
7. d) J. S. Schumm, D. L. Pearson, J. M. Tour, Angew. Chem. 1994, 106, 1445-1448; Angew. Chem. Int. Ed. Engl. 1994, 33, 1360-1363;
8. d) J. S. Schumm, D. L. Pearson, J. M. Tour, Angew. Chem. 1994, 106, 1445-1448; Angew. Chem. Int. Ed. Engl. 1994, 33, 1360-1363;
9. e) J. M. Tour, Chem. Rev. 1996, 96, 537-553;
10. f) M. D. Ward, Chem. Ind. 1996, 75, 568-573;
11. g) T. Bartik, B. Bartik, M. Brady, R. Dembinski, J. A. Gladsyz, Angew. Chem. 1996, 108, 467-469; Angew. Chem. Int. Ed. 1996, 35, 414-417;
12. g) T. Bartik, B. Bartik, M. Brady, R. Dembinski, J. A. Gladsyz, Angew. Chem. 1996, 108, 467-469; Angew. Chem. Int. Ed. 1996, 35, 414-417;
13. h) L. Jones II, D. L. Pearson, J. S. Schumm, J. M. Tour, Pure Appl. Chem. 1996, 68, 145-148.
14. a) Handbook of Conducting Polymers, Vols, 1, 2 (Ed.: T. A. Skotheim). Dekker, New York 1986;
15. b) Electronic Properties of Conjugated Polymers III: Basic Models and Applications (Eds.: H. Kuzmani, M. Mehring, S. Roth), Springer, Berlin 1989;
16. c) A. Buckley, Adv. Mater. 1992, 4, 153-158;
17. d) J. S. Miller, Adv. Mater. 1993, 5, 671-676;
18. e) 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;
19. f) N. C. Greenham, S. C. Moratti, D. D. C. Bradley, R. H. Friend, A. B. Holmes, Nature 1993, 565, 628-630;
20. g) M. Liphardt, A. Goonesekera, B. E. Jones, S. Ducharme, J. M. Takacs, L. Zhang, Science 1994, 265, 367-369;
21. h) H. S. Nalwa, Adv. Mater. 1993, 5, 341-358;
22. i) M. Brøndsted Nielsen, F. Diederich, Chem. Rec. 2002, 2, 189-198.
23. M. Bruschi, M. G. Giuffreda, H. P. Lüthi, Chem. Eur. J. 2002, 8, 4216-4227.
24. 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;
25. b) J. Anthony, A. M. Boldi, Y. Rubin, M. Hobi, V. Gramlich, C. B. Knobler, P. Seiler, F. Diederich, Helv. Chim. Acta 1995, 78, 13-45;
26. c) 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.
27. a) T. Ito, H. Shirakawa, S. Ikeda, Polym. J. 1971, 2, 231;
28. b) T. Ito, H. Shirakawa, S. Ikeda, J. Polym. Sci. Polym. Chem. Ed. 1974, 12, 11-20.
29. a) G. Wegner, Z. Naturforsch. Teil B 1969, 24, 824;
30. b) Polydiacetylenes (Ed.: H. J. Cantow), Springer, Berlin, 1984, and references therein;
31. c) Martinus Nijhoff in Polydiacetylenes, (Eds.: D. Blood, R. R. Chance), Kluwer, Dordrecht, 1985, and references therein;
32. d) D. J. Sandman, Trends Polym. Sci. 1994, 2, 44-55:
33. e) S. Okada, H. Matsuda, H. Nakanishi in Polymeric Materials Encyclopedia (Ed.: J. C. Salomone), CRC, Boca Ranton, FL, 1996, p. 8393, and references therein.
34. R. R. Tykwinski, Y. M. Zhao, Synlett. 2002, 12, 1939-1953.
35. R. R. Tykwinski, A. Hilger, F. Diederich, H. P. Lüthi, P. Seiler, V. Gramlich, J. P. Gisselbrecht, C. Boudon, M. Gross, Helv. Chim. Acta 2000, 55, 1484-1508.
36. a) Y. Rubin, C. B. Knobler, F. Diederich, Angew. Chem. 1991, 103, 708; Angew. Chem. Int. Ed. 1991, 30, 698-700;
37. a) Y. Rubin, C. B. Knobler, F. Diederich, Angew. Chem. 1991, 103, 708; Angew. Chem. Int. Ed. 1991, 30, 698-700;
38. b) R. R. Tykwinski, M. Schreiber, V. Gramlich, P. Seiler, F. Diederich, Adv. Mater. 1996, 8, 226;
39. c) C. Bosshard, R. Spreiter, P. Günter, R. R. Tykwinski, M. Schreiber, F. Diederich, Adv. Mater. 1996, 8, 231;
40. d) R. R. Tykwinski, M. Schreiber, R. Pérez Carlon, F. Diederich, V. Gramlich, Helv. Chim. Acta 1996, 79, 2249;
41. e) R. Spreiter, C. Bosshard, G. Knöpfle, P. Günter, R. R. Tykwinski, M. Schreiber, F. Diederich, J. Phys. Chem. B 1998, 102, 29-32.
42. A. Hilger, J.-P. Gisselbrecht, R. R. Tykwinski, C. Boudon, M. Schreiber, R. E. Martin, H. P. Lüthi, M. Gross, F. Diederich, J. Am. Chem. Soc. 1997, 119, 2069-2078.
43. a) T. K. Brunck, F. Weinhold, J. Am. Chem. Soc. 1979, 101, 1700-1709;
44. b) J. P. Foster, F. Weinhold, J. Am. Chem. Soc. 1980, 102, 7211-7218;
45. c) A. E. Reed, R. B. Weinstock, F. Weinhold, J. Chem. Phys. 1985, 83, 735-746;
46. d) A. E. Reed, F. Weinhold, J. Chem. Phys. 1985, 55, 1736-1740;
47. e) A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926;
48. f) F. Weinhold, J. E. Carpenter, The Structure of Small Molecules and Ions, Plenum, 1988, p. 227.
49. C. Dehu, F. Meyers, J. L. Brédas, J. Am. Chem. Soc. 1993, 115, 6198-6206.
50. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
51. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
52. W. J. Hehre, R. Dietchfield, J. A. Pople, J. Chem. Phys. 1972, 56, 2257-2261.
53. T. H. Dunning, Jr., J. Chem. Phys. 1989, 90, 1007-1023.
54. Gaussian 8 (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.
55. NBO 5.0, E. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C. M. Morales, F. Weinhold, Theoretical Chemistry Institute, University of Wisconsin, Madison, 2001.