How to build fully π-conjugated architectures with thienylene and phenylene fragments

European Journal of Organic Chemistry

Volumn , Issue 24, 2007, Pages 4019-4031

  Lois, Sandrine ^a   Florès, Jean Charles ^a   Lère Porte, Jean Pierre ^a   Serein Spirau, Françoise ^a   Moreau, Joël J E ^a   Miqueu, Karinne ^b   Sotiropoulos, Jean Marc ^b   Baylère, Patrick ^b   Tillard, Monique ^c   Belin, Claude ^c  

^a INSTITUT CHARLES GERHARDT   (France)

^b Equipe Environnement et Microbiologie   (France)

^c UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

Density functional calculations; Noncovalent interactions; Photoelectron spectroscopy; Sulfur heterocycles

Indexed keywords

EID: 34548060429     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601114     Document Type: Article

References (64)

1. J. R. Sheats, H. Antoniadis, M. Hueschen, W. Leonard, J. Miller, R. Moon, D. Roitman, A. Stocking, Science 1996, 273, 884-888.
2. a) T. A. Stockheim, R. L. Elsenbaumer, J. R. Reynolds (Eds.), Handbook of Conducting Polymers, Marcel Dekker, New York, 1998;
3. b) H. S. Nalwa (Ed.), Handbook of Organic Conductive Molecules and Polymers, vol. 1-3, John Wiley & Sons, New York, 1997.
4. R. D. Mc Cullough, P. C. Ewbank in Handbook of Conducting Polymers (Eds.: T. A. Stockheim, R. L. Elsenbaumer, J. R. Reynolds), Marcel Dekker, New York, 1998, chapter 9, pp. 225-258.
5. H. Sirringaus, P. J. Brown, R. H. Friend, M. M. Nielsen, K. Bechgaard, B. M. W. Langeveld-Voss, A. J. H. Spiering, R. A. J. Janssen, E. W. Meijer, P. Herwig, D. M. De Leeuw, Nature 1999, 401, 685-687.
6. J.-P. Lère-Porte, J. J. E. Moreau, F. Serein-Spirau, C. Torreilles, A. Righi, J.-L. Sauvajol, M. Brunet, J. Mater. Chem. 2000, 10, 927-932.
7. R. A. Silva, F. Serein-Spirau, M. Bouachrine, J.-P. Lère-Porte, J. J. E. Moreau, J. Mater. Chem. 2004, 14, 3043-3050.
8. a) S. Hotta, S. A. Lee, Synth. Met. 1999, 101, 551-552;
9. b) S. Hotta, S. A. Lee, T. Tamaki, J. Heterocycl. Chem. 2000, 37, 25-29;
10. c) S. Hotta, S. A. Lee, H. Kimura, J. Heterocycl. Chem. 2000, 37, 25-29.
11. a) M. Mushrush, A. Fachetti, M. Lefenfeld, H. E. Katz, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 9414-9423;
12. b) A. Fachetti, J. Letizia, M.-H. Yoon, M. Mushrush, H. E. Katz, T. J. Marks, Chem. Mater. 2004, 16, 4715-4727.
13. A. Pelter, I. Jenkins, D. Jones, Tetrahedron 1997, 53, 10357-10400.
14. F. Alonso, M. Yus, Tetrahedron 1991, 47, 313-316.
15. U. Wriede, M. Fernandez, K. F. West, D. Harcourt, H. W. Moore, J. Org. Chem. 1987, 52, 4485-4489.
16. T. Capecchi, C. B. de Koning, J. P. Michael, J. Chem. Soc. Perkin Trans. 1 2000, 2681-2688.
17. A.-S. Castanet, F. Colobert, P.-E. Broutin, Tetrahedron Lett. 2002, 43, 5047-5048.
18. a) M. Turbiez, P. Frère, J. Roncali, J. Org. Chem. 2003, 68, 5357-5360;
19. b) M. Turbiez, P. Frère, M. Allain, C. Videlot, J. Ackermann, J. Roncali, Chem. Eur. J. 2005, 11, 3742-3752;
20. c) I. F. Perepichka, S. Roquet, P. Leriche, J.-M. Raimundo, P. Frère, J. Roncali, Chem. Eur. J. 2006, 12, 2960-2966;
21. d) A. Dkhissi, F. Louwet, L. Groenendaal, D. Beljonne, R. Lazzaroni, J. L. Brédas, Chem. Phys. Lett. 2002, 359, 466-472.
22. F. T. Burling, B. M. Goldstein, J. Am. Chem. Soc. 1992, 114, 2313-2320.
23. Y. Nagao, T. Honjo, H. Iimori, S. Goto, S. Sano, M. Shiro, K. Yamaguchi, Y. Sei, Tetrahedron Lett. 2004, 45, 8757-8761.
24. K. M. Kim, Y.-A. Lee, O.-S. Jung, Y. S. Sohn, Bull. Korean Chem. Soc. 1996, 17, 93-95.
25. M. Pomerantz, A. S. Amarasekara, H. V. R. Dias, J. Org. Chem. 2002, 67, 6931-6937.
26. a) M. Turbiez, P. Frère, P. Blanchard, J. Roncali, Tetrahedron Lett. 2000, 41, 5521-5525;
27. b) J.-M. Raimundo, P. Blanchard, P. Frère, N. Mercier, I. Ledoux-Rak, R. Hierle, J. Roncali, Tetrahedron Lett. 2001, 42, 1507-1510.
28. J.-F. Pan, S.-J. Chua, W. Huang, Chem. Phys. Lett. 2002, 363, 18-24.
29. See for example: a) J. W. Rabalais, Principles of Ultraviolet Photoelectron Spectroscopy, John Wiley & Sons, New York, 1977;
30. b) U. Lottermoser, P. Rademacher, M. Mazik, K. Kowski, Eur. J. Org. Chem. 2005, 522-531:
31. c) P. Rademacher, Chem. Rev. 2003, 103, 933-976.
32. C. N. R. Rao, P. K. Basu, M. S. Hegde, Systematic Organic UV Photoelectron Spectroscopy, Marcel Dekker, New York, 1979.
33. See for example: H. Bock, B. Roth, Phosphorus Sulfur 1983, 14, 211-223.
34. a) J.-J. Yeh, Atomic Calculation of Photoionisation Cross-Sections and Asymmetry Parameters, Gordon and Breach Science Publishers, Langhorne, PE, 1993;
35. b) I. P. Csonka, G. Vass, L. Szepes, D. Szabo, I. Kapovits, J. Mol. Struct. (THEOCHEM) 1998, 455, 141-159.
36. V. I. Minkin, R. M. Minyaev, Mendeleev Commun. 2000, 5, 167-206.
37. G. D. Markham, C. W. Bock, J. Mol. Struct. (THEOCHEM) 1997, 418, 139-154.
38. M. Iwaoka, H. Komatsu, T. Katsuda, S. Tomoda, J. Am. Chem. Soc. 2004, 126, 5309-5317.
39. A. F. Cozzolino, I. Vargas-Baca, S. Mansour, A. H. Mahmoudkhani, J. Am. Chem. Soc. 2005, 127, 3184-3190.
40. J. Wolfe, R. Singer, B. Yang, S. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550-9561.
41. 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. Stratman, 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. K. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowswi, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Jonhson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh, PA, 2001 (A.11.1) or 2002 (A.11.3).
42. W. J. Hehre, L. Radom, P. v. R. Schleyer, J. A. Pople, Ab initio Molecular Orbital Theory, John Wiley & Sons, New York, 1986.
43. R. G. Parr, W. Yang, Functional Theory of Atoms and Molecules (Eds.: R. Breslow, J. B. Goodenough), Oxford University Press, New York, 1989.
44. a) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100;
45. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652:
46. c) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
47. a) M. A. De Oliveira, H. F. Dos Santos, W. B. De Almeida, Phys. Chem. Chem. Phys. 2000, 2, 3373-3380;
48. b) D. Delaere, M. T. Nguyen, L. G. Vanquickenborne, J. Phys. Chem. A 2003, 107, 838-846.
49. D. Delaere, M. T. Nguyen, L. G. Vanquickerborne, J. Phys. Chem. A 2003, 107, 838-846.
50. P. Blanchard, P. Verlhac, L. Michaux, P. Frère, J. Roncali, Chem. Eur. J. 2006, 12, 1244-1255.
51. a) A. E. Reed, L. A. Curtiss, F. Weinhold, J. Chem. Rev. 1988, 88, 899-926;
52. b) J. P. Foster, F. Weinhold, J. Am. Chem. Soc. 1980, 102, 7211-7218.
53. [39] The first estimated IP is taken to be equal to the first experimental ionisation potential.
54. R. Stowasser, R. Hoffmann, J. Am. Chem. Soc. 1999, 121, 3414-3420.
55. A. J. Arduengo III, H. Bock, H. Chen, M. Denk, D. A. Dixon, J. C. Green, W. A. Hermann, N. L. Jones, M. Wagner, R. West, J. Am. Chem. Soc. 1994, 116, 6641-6649.
56. a) H. M. Muchall, P. Rademacher, J. Mol. Struct. 1997, 435, 157-167;
57. b) H. M. Muchall, P. Rademacher, J. Mol. Struct. 1998, 471, 189-194;
58. c) H. M. Muchall, N. H. Werstiuk, B. Choudhurry, Can. J. Chem. 1998, 76, 221-227;
59. d) H. M. Muchall, N. H. Werstiuk, B. Choudhurry, J. Ma, J. Warkentin, J. P. Pezacki, Can. J. Chem. 1998, 76, 238-240.
60. a) P. F. Flükiger, "Development of the molecular graphics package MOLEKEL and its application to selected problems in organic and organometallic chemistry", Ph. D. Dissertation, University of Geneva, 1992;
61. b) MOLEKEL: An Interactive Molecular Graphics Tool: S. Portmann, H. P. Lüthi, Chimia 2000, 54, 766-770.
62. CrysAlisCCD and CrysAlisRed 169 software package. 2001, Oxford Diffraction, Ltd., Abingdon, UK.
63. G. M. Sheldrick, SHELXS-97: A Program for Crystal Structures Solution, 1997, University of Göttingen, Germany.
64. G. M. Sheldrick, SHELXL-97: A Program for Refining Crystal Structures, 1997, University of Göttingen, Germany.