Luminescent, redox-active diphenothiazine dumbbells expanded by conjugated arenes and heteroarenes

Journal of Organic Chemistry

Volumn 75, Issue 24, 2010, Pages 8591-8603

  Hauck, Martina ^a   Turdean, Raluca ^a,b   Memminger, Karin ^a,c   Schönhaber, Jan ^a   Rominger, Frank ^c   Muller T J J ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b BABE BOLYAI UNIVERSITY   (Romania)

^c UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC MOIETIES; COPLANARITY; DFT COMPUTATIONS; ELECTRON CONJUGATION; ELECTRON TRANSMISSION; ELECTRONIC COUPLING; ENERGY CONFORMERS; GOOD YIELD; HETEROARENES; REDOX-ACTIVE; REVERSIBLE OXIDATION; SUZUKI-MIYAURA COUPLING;

AROMATIC COMPOUNDS; CHEMICAL REACTIONS; ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; EXCITED STATES; LUMINESCENCE; PHOTOEXCITATION;

DENSITY FUNCTIONAL THEORY;

PHENOTHIAZINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTRON TRANSPORT; ELECTROPHORESIS; FLUORESCENCE; GEOMETRY; LUMINESCENCE; OXIDATION REDUCTION POTENTIAL; SYNTHESIS;

EID: 78650377372     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101997t     Document Type: Article

References (70)

1. For a monograph, see: Functional Organic Materials-Synthesis, Strategies, and Applications, Müller, T. J. J. and Bunz, U. H. F., Eds.; Wiley-VCH: Weinheim, 2007.
2. Oka, H. J. Mater. Chem. 2008, 18, 1927-1934
3. Okamato, T.; Kuratsu, M.; Kozaki, M.; Hirotsu, K.; Ichimura, A.; Matsushita, T.; Okada, K. Org. Lett. 2004, 6, 3493-3496
4. Sun, D.; Rosokha, S. V.; Kochi, J. K. J. Am. Chem. Soc. 2004, 126, 1388-1401
5. Kochi, J. K.; Rathore, R.; Le Maguères, P. J. Org. Chem. 2000, 65, 6826-6836
6. Nishinaga, T.; Inoue, R.; Matsuura, A.; Komatsu, K. Org. Lett. 2002, 4, 1435-1438
7. Pan, D.; Philips, D. L. J. Phys. Chem. A 1999, 103, 4737-4743
8. Müller, T. J. J. Tetrahedron Lett. 1999, 40, 6563-6566
9. Krämer, C. S.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2000, 2, 3723-3726
10. Barkschat, C. S.; Guckenberger, R.; Müller, T. J. J. Z. Naturforsch. 2009, 64b, 707-718
11. Franz, A. W.; Stoycheva, S.; Himmelhaus, M.; Müller, T. J. J. Beilstein J. Org. Chem. 2010, 6; published July 2, 2010; DOI: 10.3762/bjoc.6.72.
12. Barkschat, C. S.; Stoycheva, S.; Himmelhaus, M.; Müller, T. J. J. Chem. Mater. 2010, 22, 52-63
13. Lambert, C.; Kriegisch, V. Langmuir 2006, 22, 8807-8812
14. Uchida, T.; Ito, M.; Kozawa, K. Bull. Chem. Soc. Jpn. 1983, 56, 577-582
15. Müller, T. J. J.; Franz, A. W.; Barkschat (née Krämer), C. S.; Sailer, M.; Meerholz, K.; Müller, D.; Colsmann, A.; Lemmer, U. Macromol. Symp. 2010, 287, 1-7
16. McDowell, J. J. H. Acta Crystallogr., Sect. B: Found. Crystallogr. 1976, B32, 5-10
17. Krämer, C. S.; Müller, T. J. J. Eur. J. Org. Chem. 2003, 3534-3548
18. Sailer, M.; Nonnenmacher, M.; Oeser, T.; Müller, T. J. J. Eur. J. Org. Chem. 2006, 423-435
19. Franz, A. W.; F. Rominger, F.; Müller, T. J. J. J. Org. Chem. 2008, 73, 1795-1802
20. Sailer, M.; Franz, A. W.; Müller, T. J. J. Chem.-Eur. J. 2008, 14, 2602-2614
21. Franz, A. W.; Popa, L. N.; Müller, T. J. J. Tetrahedron Lett. 2008, 49, 3300-3303
22. Franz, A. W.; Popa, L. N.; Rominger, F.; Müller, T. J. J. Org. Biomol. Chem. 2009, 7, 469-475
23. Krämer, C. S.; Zeitler, K.; Müller, T. J. J. Tetrahedron Lett. 2001, 42, 8619-8624
24. Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. 1995, 34, 1348-1350
25. Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609-3612
26. For reviews, see: Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; pp 1051 - 1096.
27. Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131-209
28. For an excellent overview of modern aromatic carbon-nitrogen cross-coupling reactions, see: Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; De Meijere, A.; Diederich, F., Eds.; Wiley-VCH: New York, 2004; pp 699 - 760 and references therein.
29. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483
30. Suzuki, A. In Metal Catalyzed Cross Coupling Reactions; Stang, P. J.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 1998; pp 49 - 97.
31. Stanforth, S. P. Tetrahedron 1998, 54, 263-303
32. Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168
33. Franz, A. W.; Müller, T. J. J. Synthesis 2008, 1121-1125
34. Muschelknautz, C.; Sailer, M.; Müller, T. J. J. Synlett 2008, 845-848
35. Sailer, M.; Rominger, F.; Müller, T. J. J. J. Organomet. Chem. 2006, 691, 299-308
36. Sailer, M.; Gropeanu, R.-A.; Müller, T. J. J. J. Org. Chem. 2003, 68, 7509-7512
37. Krämer, C. S.; Zimmermann, T. J.; Sailer, M.; Müller, T. J. J. Synthesis 2002, 1163-1170
38. Schlichting, P.; Rohr, U.; Müllen, K. Liebigs Ann./Recueil 1997, 395-407
39. Yang, C.; Jacob, J.; Müllen, K. Macromolecules 2006, 39, 5696-5704
40. Zhu, Y.; Rabindranath, A. R.; Beyerlein, T.; Tieke, B. Macromolecules 2007, 6981-6989
41. Schareina, T.; Zapf, A.; Beller, M. Chem. Commun. 2004, 1388-1389
42. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 795807 (2n). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. (Fax: + 44-1223/336-033. E-mail: deposit@ccdc.cam.ac.uk) .
43. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
44. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377
45. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
46. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724-728
47. Frisch, M. J. et al. Gaussian 03, Revision B.03; Gaussian, Inc.: Wallingford, CT, 2004.
48. Calculated for the 3,10-bridged isomer.
49. Woitellier, S.; Launay, J. P.; Joachim, C. Chem. Phys. 1989, 131, 481-488
50. Clarke, D.; Gilbert, B. C.; Hanson, P.; Kirk, C. M. J. Chem. Soc., Perkin Trans. 2 1978, 1103-1110
51. Du, H.; Fuh, R. A.; Li, J.; Corkan, A.; Lindsey, J. S. Photochem. Photobiol. 1998, 68, 141-142
52. Magdesieva, T. V.; Kukhareva, I. I.; Shaposhnikova, E. N.; Artamkina, G. A.; Beletskaya, I. P.; Butin, K. P. J. Organomet. Chem. 1996, 526, 51-58
53. Fukuzumi, S.; Ohkubo, K.; Imahori, H.; Guldi, D. M. Chem.-Eur. J. 2003, 9, 1585-1593
54. Donkers, R. L.; Maran, F.; Wayner, D. D. M.; Workentin, M. S. J. Am. Chem. Soc. 1999, 121, 7239-7248
55. Dietrich, M.; Heinze, J. J. Am. Chem. Soc. 1990, 112, 5142-5145
56. Fichou, D.; Nunzi, J.-M.; Charra, F.; Pfeffer, N. Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A 1994, 255, 73-84
57. Inoue, S.; Jigami, T.; Nozoe, H.; Otsubo, T.; Ogura, F. Tetrahedron Lett. 1994, 35, 8009-8012
58. Ortiz, R. P.; Casado, J.; Hernández, V.; Navarrete, J. T. L.; Letizia, J. A.; Ratner, M. A.; Facchetti, A.; Marks, T. J. Chem.-Eur. J. 2009, 15, 5023-5039
59. Yang, L.; Feng, J.-K.; Ren, A.-M. J. Org. Chem. 2005, 70, 5987-5996
60. Valeur, B. Molecular Fluorescence; Wiley-VCH: Weinheim, 2002.
61. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 3 rd ed.; Springer: New York, 2006.
62. Li, H.; Dupre, P.; Kong, W. Chem. Phys. Lett. 1997, 273, 272-278
63. Organikum, 21 st ed.; Becker, H. G. O.; Beckert, R.; Domschke, G.; Fanghänel, E.; Habicher, W. D.; Metz, P.; Pavel, D.; Schwetlick, K. Wiley-VCH: Weinheim, New York, Chichester, Brisbane, Singapore, Toronto, 2001.
64. Miller, L. L.; Yu, Y. J. Org. Chem. 1995, 60, 6813-6819
65. Sonnenschein, M.; Amirav, A.; Jortner, J. J. Phys. Chem. 1984, 88, 4218-4222
66. Nad, S.; Pal, H. J. Phys. Chem. A 2001, 105, 1097-1106
67. Melhuish, H. J. Phys. Chem. 1961, 65, 229-235
68. Jones, G., II; Rahman, M. A. J. Phys. Chem. 1994, 98, 13028-13037
69. Hamai, S.; Hirayama, F. J. Phys. Chem. 1983, 87, 83-89
70. Zanello, P. In Ferrocenes; Togni, A.; Hayashi, T., Eds.; VCH: Weinheim, New York, Basel, Cambridge, Tokyo, 1995; pp 317 - 430.