Selective tuning of the band gap of π-conjugated dithieno[3,2-6: 2′,3′-d]phospholes toward different emission colors

Chemistry - A European Journal

Volumn 13, Issue 26, 2007, Pages 7487-7500

  Dienes, Yvonne ^a   Durben, Stefan ^a,c   Kárpáti, Tamás ^b   Neumann, Toni ^a   Englert, Ulli ^a   Nyulászi, László ^b   Baumgartner, Thomas ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^c UNIVERSITY OF CALGARY   (Canada)

Author keywords

Cross coupling; Density functional calculations; Luminescence; Organic electronics

Indexed keywords

DENSITY FUNCTIONAL THEORY; ENERGY GAP; HALOGEN COMPOUNDS; LUMINESCENCE; SCAFFOLDS;

CONJUGATED SYSTEM; CROSS-COUPLING; ORGANIC ELECTRONICS;

CONJUGATED POLYMERS;

EID: 34548804972     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700399     Document Type: Article

References (90)

1. a) Conjugated Conducting Polymers, Vol. 102 (Ed.: H. Kiess), Springer, New York, 1992;
2. b) H. S. Nalwa, Handbook of conductive materials and polymers, Wiley, New York, 1997;
3. c) Handbook of Conducting Polymers (Eds.: T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds), 2nd ed., Marcel Dekker, New York 1998.
4. a) K. Müllen, G. Wegner, Electronic Materials: The Oligomer Approach, Wiley-VCH, Weinheim, 1998;
5. b) P. F. H. Schwab, J. R. Smith, J. Michl, Chem. Rev. 2005, 105, 1197;
6. c) F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491;
7. d) J. Roncali, Chem. Rev. 1997, 97, 173;
8. e) R. E. Martin, F. Diederich, Angew. Chem. 1999, 111, 1440;
9. Angew. Chem. Int. Ed. 1999, 38, 1350.
10. Handbook of Oligo- and Polythiophenes (Ed.: D. Fichou), Wiley-VCH, Weinheim, 1998.
11. Organic Light Emitting Devices (Eds.: K. Müllen, U. Scherf), Wiley-VCH, Weinheim, 2005.
12. a) A. Kraft, A. C. Grimsdale, A. B. Holmes, Angew. Chem. 1998, 110, 416;
13. Angew. Chem. Int. Ed. 1998, 37, 402;
14. b) U. Mitschke, P. Bäuerle, J. Mater. Chem. 2000, 10, 1471;
15. c) A. P. Kulkarni, C. J. Tonzola, A. Babel, S. A. Jenekhe, Chem. Mater. 2004, 16, 4556;
16. d) C.-T. Chen, Chem. Mater. 2004, 16, 4389;
17. e) B. W. D'Andrade, S. R. Forrest, Adv. Mater. 2004, 16, 1585.
18. a) C. D. Dimitrakopoulos, P. R. L. Malenfant, Adv. Mater. 2002, 14, 99;
19. b) H. E. Katz, Z. Bao, S. L. Gilat, Acc. Chem. Res. 2001, 34, 359;
20. c) J. A. Rogers, Z. Bao, H. E. Katz, A. Dodabalapur, in Thin-Film Transistors (Eds.: C. R. Kagan, P. Andry), Marcel Dekker, New York 2003, p. 377;
21. d) V. C. Sundar, J. Zaumseil, V. Podzorov, E. Menard, R. L. Willett, T. Someya, M. E. Gershenson, J. A. Rogers, Science 2004, 303, 1644;
22. e) Z. Bao, Nat. Mater. 2004, 3, 137;
23. f) N. Stutzmann, R. H. Friend, H. Sirringhaus, Science 2003, 299, 1881;
24. g) G. H. Gelinck, H. E. A. Huitema, E. van Veenendaal, E. Cantatore, L. Schrijnemakers, J. B. P. H. van der Putten, T. C. T. Geuns, M. Beenhakkers, J. B. Giesbers, B.-H. Huisman, E. J. Meijer, E. M. Benito, F. J. Touwslager, A. W. Marsman, B. J. E. van Rens, D. M. de Leeuw, Nat. Mater. 2004, 3, 106;
25. h) S. R. Forrest, Nature 2004, 428, 911;
26. i) E. J. Meijer, D. M. DeLeeuw, S. Setayesh, E. van Veenendaal, B.-H. Huisman, P. W. M. Blom, J. C. Hummelen, U. Scherf, T. M. Klapwijk, Nat. Mater. 2003, 2, 678.
27. a) C. W. Tang, S. A. Van Slyke, J. Appl. Phys. 1987, 51, 913;
28. b) C. W. Tang, S. A. Van Slyke, C. H. Chen, J. Appl. Phys. 1989, 65, 3610;
29. c) J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks. K. Mackay, R. H. Friend, P. L. Burns, A. B. Holmes, Nature 1990, 347, 539;
30. d) M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest, Nature 1998, 395, 151.
31. a) T. Baumgartner, R. Réau, Chem. Rev. 2006, 106, 4681;
32. b) F. Mathey, Angew. Chem. 2003, 115. 1616;
33. Angew. Chem. Int. Ed. 2003, 42, 1578;
34. c) D. P. Gates, Top. Curr. Chem. 2005, 250, 107;
35. d) M. Hissler, P. W. Dyer, R. Réau, Top. Curr. Chem. 2005, 250, 127;
36. e) Z. Jin, B. L. Lucht, I. Organomet. Chem. 2002, 653, 167;
37. f) D. Delaere. M. T. Nguyen, L. G. Vanquickenborne, Phys. Chem. Chem. Phys. 2002, 4. 1522;
38. g) D. Delaere, M. T. Nguyen, L. G. Vanquickenborne, J. Phys. Chem. A 2003, 107, 838;
39. h) J. Ma. S. Li, Y. Jiang, Macromolecules 2002, 35, 1109.
40. J. Roncali, Chem. Rev. 1997, 97, 173.
41. a) Phosphorus: The Carbon Copy (Eds.: K. Dillon, F. Mathey, J. F. Nixon), Wiley, Chichester, 1998;
42. b) Houben Weyl, Methods of Organic Chemistry, Vol. E1 & E2: Organic Phosphorus compounds I & II (Ed.: M. Regitz), Thieme, Stuttgart, 1982;
43. c) F. Mathey, A. Sevin, Molecular Chemistry of the Transition Metals, Wiley, Chichester, 1996.
44. a) C. Hay, D. Le Vilain, V. Deborde, L. Toupet, R. Réau, Chem. Commun. 1999, 345;
45. b) C. Hay, C. Fischmeister, M. Hissler, L. Toupet, R. Réau, Angew. Chem. 2000, 112, 1882;
46. Angew. Chem. Int. Ed. 2000, 39, 1812;
47. c) C. Hay, M. Hissler, C. Fischmeister, J. Rault-Berthelot, L. Toupet, L. Nyulászi, R. Réau, Chem. Eur. J. 2001, 7, 4222;
48. d) C. Fave, M. Hissler, T. Kárpáti, J. Rault-Berthelot, V. Deborde, L. Toupet, L. Nyulászi, R. Réau, J. Am. Chem. Soc. 2004, 126, 6059.
49. a) C. Fave, T.-Y. Cho, M. Hissler, C.-W. Chen, T.-Y. Luh, C.-C. Wu, R. Réau, J. Am. Chem. Soc. 2003, 125, 9254;
50. b) H.-C. Su, O. Fadhel, C.-J. Yang, T.-Y. Cho, C. Fave, M. Hissler, C.-C. Wu, R. Réau, J. Am. Chem. Soc. 2006, 128, 983.
51. a) T. Baumgartner, T. Neumann, B. Wirges, Angew. Chem. 2004, 116, 6323;
52. Angew. Chem. Int. Ed. 2004, 43, 6197;
53. b) T. Baumgartner, W. Bergmans, T. Kárpáti, T. Neumann, M. Nieger, L. Nyulászi, Chem. Eur. J. 2005, 11, 4687.
54. a) T. Baumgartner, J. Inorg. Organomet. Polym. Mater. 2005, 15, 389;
55. b) X. Zhang, A. J. Matzger, J. Org. Chem. 2003, 68, 9813;
56. c) S. Y. Hong, J. M. Song, J. Chem. Phys. 1997, 107, 10607.
57. F. Mathey, Chem. Rev. 1988, 88, 429.
58. a) T. Baumgartner, W. Wilk, Org. Lett. 2006, 8, 503;
59. b) Y. Dienes, M. Eggenstein, T. Neumann, U. Englert, T. Baumgartner, Dalton Trans. 2006, 1424;
60. c) T. Neumann, Y. Dienes, T. Baumgartner, Org. Lett. 2006, 8, 495.
61. Z. Zhang. J. Li, B. Huang, J. Qin, Chem. Lett. 2006, 35, 958.
62. G. A. Sotzing, J. R. Reynolds, P. J. Steel, Chem. Mater. 1996, 8, 882.
63. The reaction conditions also provide 5, when the oxidized dithieno-phosphole 3(=O) is used as starting material.
64. Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004.
65. a) J. Ohshita, H. Kai, A. Takata, T. Iida, N. Ohta, K. Komaguchi, M. Shiotani, A. Adachi, K. Sakamaki, K. Okita, Organometallics 2001, 20, 4800;
66. b) G. Barbarella, L. Favaretto, G. Sotgiu, L. Antolini, G. Gigli, R. Cingolani, A. Bongini, Chem. Mater. 2001, 13, 4112;
67. c) G. Sotgiu, M. Zambianchi, G. Barabarella, F. Aruffo, F. Cipriani, A. Ventola, J. Org. Chem. 2003, 68, 1512;
68. d) K. R. Radke, K. Ogawa, S. C. Rasmussen, Org. Lett. 2005, 7, 5253.
69. E. C. Constable. Prog. Inorg. Chem. 1994, 42, 67.
70. C. Amari, S. Ianelli, C. Pelizzi, G. Pelizzi, G. Predieri, Inorg. Chim. Acta 1993, 211, 89.
71. a) M. Malagoli, J. Bredas, Chem. Phys. Lett. 2000, 327, 13;
72. b) X.-J. Liu, J.-K. Feng, A.-M. Ren. X. Zhou, H. Cheng, Chem. Phys. 2004, 507, 61.
73. a) Y. Shirota, J. Mater. Chem. 2000, 10, 1;
74. b) T. Noda, H. Ogawa, N. Noma, Y. Shirota, Adv. Mater. 1997, 9, 720;
75. c) T. Noda, H. Ogawa, N. Noma, Y. Shirota, J. Mater. Chem. 1999, 9, 2177.
76. A. Modelli, Trends Chem. Phys. (Res. Trends) 1997, 6, 57.
77. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, 2nd ed., Springer, New York, 2004.
78. We have recently reported a related polyelectrolyte based on cationic phosphorus centers, see: S. Durben, Y. Dienes, T. Baumgartner, Org. Lett. 2006, 8, 5893.
79. H. Schmidbaur, W. Graf, G. Müller, Angew. Chem. 1988, 100, 439;
80. Angew. Chem. Int. Ed. Engl. 1988, 27, 417.
81. a) Y.-A. Lee, J. E. McGarrah, R. J. Lachicotte, R. Eisenberg, J. Am. Chem. Soc. 2002, 124, 10663;
82. b) V. W. W. Yam, C.-L. Chang, C.-K. Li, K. M.-C. Wong, Coord. Chem. Rev. 2001, 216-217, 173.
83. T. L. Stott, M. O. Wolf, B. O. Patrick, Inorg. Chem. 2005, 44, 620.
84. A. D. Becke, J. Chem. Phys. 1993, 98, 5648;
85. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
86. Gaussian 03, Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian Inc., Wallingford, CT, 2004.
87. C. W. Bird, Tetrahedron 1990, 46, 5697.
88. W. Gordy, J. Chem. Phys. 1947, 15, 305.
89. P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van Eikemma Hommes, J. Am. Chem. Soc. 1996, 118, 6317.
90. R. Usón, A. Laguna, M. Laguna, Inorg. Synth. 1989, 26, 85.