Triphenylene analogues with B2N2C2 cores: Synthesis, structure, redox behavior, and photophysical properties

Journal of the American Chemical Society

Volumn 128, Issue 33, 2006, Pages 10885-10896

  Jaska, Cory A ^a   Emslie, David J H ^a,b   Bosdet, Michael J D ^a   Piers, Warren E ^a   Sorensen, Ted S ^a   Parvez, Masood ^a  

^a UNIVERSITY OF CALGARY   (Canada)

^b MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC PHYSICS; CRYSTAL STRUCTURE; ELECTRON TRANSITIONS; ORGANIC SOLVENTS; REDOX REACTIONS; SYNTHESIS (CHEMICAL);

HETEROAROMATIC TRIPHENYLENE; PHOTOPHYSICAL PROPERTIES; PYRIDAZINE DERIVATIVES; REDOX BEHAVIOR;

AROMATIC HYDROCARBONS;

AROMATIC COMPOUND; BENZENE DERIVATIVE; BORON; CARBON; HYDROGEN; LEWIS ACID; NITROGEN; PYRIDAZINE DERIVATIVE; TRIPHENYLENE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHELATION; CRYSTAL STRUCTURE; ELECTRON SPIN RESONANCE; FLUORESCENCE; LIGHT; OXIDATION REDUCTION REACTION; REDUCTION; STEREOSPECIFICITY; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33747784612     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja063519p     Document Type: Article

References (85)

1. (a) Mullen, K.; Rabe, J. P. Ann. NY Acad. Sci. 1998, 852, 205.
2. (b) Watson, M. D.; Fechtenkotter, A.; Mullen, K. Chem. Rev. 2001, 101, 1267.
3. (c) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891.
4. (a) McKenna, M. D.; Barbera, J.; Marcos, M.; Serrano, J. L. J. Am. Chem. Soc. 2005, 127, 619.
5. (b) Ikeda, M.; Takeuchi, M.; Shinkai, S. Chem. Commun. 2003, 1354.
6. (c) Barbera, J.; Garces, A. C.; Jayaraman, N.; Omenat, A.; Serrano, J. L.; Stoddart, J. F. Adv. Mater. 2001, 13, 175.
7. (d) Paraschiv, I.; Giesbers, M.; van Lagen, B.; Grozema, F. C.; Abellon, R. D.; Siebbeles, L. D. A.; Marcelis, A. T. M.; Zuilhof, H.; Sudholter, E. J. R. Chem. Mater. 2006, 18, 968.
8. (a) Freudenmann, R.; Behnisch, B.; Hanack, M. J. Mater. Chem. 2001, 11, 1618.
9. (b) Seguy, I.; Jolinat, P.; Destruel, P.; Farenc, J.; Mamy, R.; Bock, H.; Ip, J.; Nguyen, T. P. J. Appl. Phys. 2001, 89, 5442.
10. (a) Kumar, S. Curr. Sci. 2002, 82, 256.
11. (b) Oukachmih, M.; Destruel, P.; Seguy, I.; Ablart, G.; Jolinat, P.; Archambeau, S.; Mabiala, M.; Fouet, S.; Bock, H. Sol. Energy Mater. Sol. Cells 2005, 85, 535.
12. (a) Adam, D.; Closs, F.; Frey, T.; Funhoff, D.; Haarer, D.; Ringsdorf, H.; Schuhmacher, P.; Siemensmeyer, K. Phys. Rev. Lett. 1993, 70, 457.
13. (b) Adam, D.; Schuhmacher, P.; Simmerer, J.; Haussling, L.; Siemensmeyer, K.; Etzbachi, K. H.; Ringsdorf, H.; Haarer, D. Nature 1994, 371, 141.
14. (a) Pieterse, K.; van Hal, P. A.; Kleppinger, R.; Vekemans, J. A. J. M.; Janssen, R. A. J.; Meijer, E. W. Chem. Mater. 2001, 13, 2675.
15. (b) Gearba, R. I.; Lehmann, M.; Levin, J.; Ivanov, D. A.; Koch, M. H. J.; Barbera, J.; Debije, M. G.; Piris, J.; Geerts, Y. H. Adv. Mater. 2003, 15, 1614.
16. (c) Crispin, X.; Cornil, J.; Friedlein, R.; Okudaira, K. K.; Lemaur, V.; Crispin, A.; Kestemont, G.; Lehmann, M.; Fahlman, M.; Lazzaroni, R.; Geerts, Y.; Wendin, G.; Ueno, N.; Bredas, J. L.; Salaneck, W. R. J. Am. Chem. Soc. 2004, 126, 11889.
17. (d) Chang, T. H.; Wu, B. R.; Chiang, M. Y.; Liao, S. C.; Ong, C. W.; Hsu, H. F.; Lin, S. Y. Org. Lett. 2005, 7, 4075.
18. (a) Yamaguchi, S.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2000, 122, 6335.
19. (b) Yamaguchi, S.; Shirasaka, T.; Tamao, K. Org. Lett. 2000, 2, 4129.
20. (c) Yamaguchi, S.; Shirasaka, T.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2002, 124, 8816.
21. (d) Wakamiya, A.; Ide, T.; Yamaguchi, S. J. Am. Chem. Soc. 2005, 127, 14859.
22. (a) Yamaguchi, S.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2001, 123, 11372.
23. (b) Kubo, Y.; Yamamoto, M.; Ikeda, M.; Takeuchi, M.; Shinkai, S.; Yamaguchi, S.; Tamao, K. Angew. Chem., Int. Ed. 2003, 42, 2036.
24. (a) Fu, G. C. Adv. Organomet. Chem. 2001, 47, 101.
25. (b) Herberich, G. E.; Ohst, H. Adv. Organomet. Chem. 1986, 25, 199.
26. Chissick, S. S.; Dewar, M. J. S.; Maitlis, P. M. Tetrahedron Lett. 1960, 1 (44), 8.
27. (a) Dewar, M. J. S.; Dietz, R. J. Chem. Soc. 1959, 2728.
28. A more recent paper has reinvestigated this work; see: (b) Paetzold, P.; Stanescu, C.; Stubenrauch, J. R.; Bienmuller, M.; Englert, U. Z. Anorg. Allg. Chem. 2004, 630, 2632.
29. Dewar, M. J. S.; Kubba, V. P.; Pettit, R. J. Chem. Soc. 1958, 3073.
30. (a) Van Veen, R.; Bickelhaupt, F. J. Organomet. Chem. 1971, 30, C51.
31. (b) Van Veen, R.; Bickelhaupt, F. J. Organomet. Chem. 1974, 77, 153.
32. Jutzi, P. Angew. Chem., Int. Ed. Engl. 1972, 11, 53.
33. (a) Boese, R.; Finke, N.; Henkelmann, J.; Maier, G.; Paetzold, P.; Reisenauer, H. P.; Schmid, G. Chem. Ber. 1985, 118, 1644.
34. (b) Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W.; Young, V. G., Jr. Angew. Chem., Int. Ed. Engl. 1997, 36, 2014.
35. (c) Ashe, A. J., III; Fang, X.; Kampf, J. W. Organometallics 1999, 18, 466.
36. (d) Herberich, G. E.; Cura, E.; Ni, J. Inorg. Chem. Commun. 1999, 2, 503.
37. Culling, G. C.; Dewar, M. J. S.; Marr, P. A. J. Am. Chem. Soc. 1964, 86, 1125.
38. However, these compounds were poorly characterized by present day standards, relying primarily on elemental analysis and molecular weight determinations for structural elucidation, with no further investigations into their resulting optical or electronic properties.
39. Fang, X.; Yang, H.; Kampf, J. W.; Banaszak Holl, M. M.; Ashe, A. J., III, Organometallics 2006, 25, 513.
40. (a) Hagenau, U.; Heck, J.; Hendrickx, E.; Persoons, A.; Schuld, T.; Wong, H. Inorg. Chem. 1996, 35, 7863.
41. (b) Behrens, U.; Meyer-Friedrichsen, T.; Heck, J. Z. Anorg. Allg. Chem. 2003, 629, 1421.
42. (a) Lee, B. Y.; Wang, S.; Putzer, M.; Bartholomew, G. P.; Bu, X.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 3969.
43. (b) Lee, B. Y.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 8577.
44. (a) Emslie, D. J. H.; Piers, W. E.; Parvez, M. Angew. Chem., Int. Ed. 2003, 42, 1252.
45. (b) Ghesner, I.; Piers, W. E.; Parvez, M.; McDonald, R. Organometallics 2004, 23, 3085.
46. IUPAC name: bisborino[1.2-c:2′,1′-e]pyridazino[1,2-a][1,2,3, 6]-diazadiborine.
47. (a) Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317.
48. (b) Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Chem. Rev. 2005, 105, 3842.
49. The NICS method is a measure of the abnormal proton chemical shift of aromatic molecules by the induced ring current that is due to cyclic σ or π electron delocalization, and whose values can either be negative (suggestive of diatropic ring currents and aromaticity) or positive (suggestive of paratropic ring currents and antiaromaticity). The standard method for NICS calculations is NICS(1), which is calculated at a distance of 1 Å above the plane of the ring in order to minimize the influence from the σ framework while maximizing the contributions from the π system.
50. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746.
51. Schleyer, P. v. R.; Jiao, H.; Hommes, N. J. R. v. E.; Malkin, V. G.; Malkina, O. L. J. Am. Chem. Soc. 1997, 119, 12669.
52. Siebert, W.; Full, R.; Schmidt, H.; von Seyerl, J.; Halstenberg, M.; Huttner, G. J. Organomet. Chem. 1980, 191, 15.
53. (a) Fowler, P. W.; Steiner, E. J. Phys. Chem. A 1997, 101, 1409.
54. (b) Soncini, A.; Domene, C.; Engelberts, J. J.; Fowler, P. W.; Rassat, A.; van Lenthe, J. H.; Havenith, R. W. A.; Jenneskens, L. W. Chem.-Eur. J. 2005, 11, 1257.
55. Cernusak, I.; Fowler, P. W.; Steiner, E. Mol. Phys. 2000, 98, 945.
56. A NICS(1) value of -12.50 ppm was reported recently for pyridazine: Fabian, J.; Lewars, E. Can. J. Chem. 2004, 82, 50.
57. 6 rings of 5 had NICS values similar to those of benzene (-10.33 ppm), indicating a high degree of aromaticity in these rings.
58. Collings, J. C.; Roscoe, K. P.; Thomas, R. L.; Batsonov, A. S.; Stimson, L. M.; Howard, J. A. K.; Marder, T. B. New J. Chem. 2001, 25, 1410.
59. Charbonneau, G. P.; Delugeard, Y. Acta Crystallogr. B 1977, 33, 1586.
60. Blake, A. J.; Rankin, D. W. H. Acta Crystallogr. C 1991, 47, 1933.
61. Meerholz, K.; Heinze, J. J. Am. Chem. Soc. 1989, 111, 2325.
62. Dietrich, M.; Heinze, J. J. Am. Chem. Soc. 1990, 112, 5142.
63. (a) Lemaire, O.; De Backer, M.; Devos, A.; Sauvage, F. X. Synth. Met. 2001, 123, 61.
64. (b) Jones, M. T.; Ahmed, R. H. J. Phys. Chem. 1980, 84, 2913.
65. (c) Arick, M. R.; van Broekhoven, J. A. M.; Pijpers, F. W.; de Boer, E. J. Am. Chem. Soc. 1972, 94, 7531.
66. (d) de Boer, E.; Grotens, A. M.; Smid, J. J. Am. Chem. Soc. 1970, 92, 4742.
67. Lichtblau, A.; Kaim, W.; Schulz, A.; Stahl, T. J. Chem. Soc., Perkin Trans. 2 1992, 1497.
68. Schnieders, C; Mullen, K.; Huber, W. Tetrahedron 1984, 40, 1701.
69. (a) Berlman, I. B. Handbook of Fluorescence Spectra of Aromatic Molecules; Academic Press: New York, 1971.
70. (b) Becker, R. S. Theory and Interpretation of Fluorescence and Phosphorescence; Wiley-Interscience: New York, 1969.
71. (c) Sharma, A.; Schulman, S. G. Introduction to Fluorescence Spectroscopy; Wiley-Interscience: New York, 1999.
72. (a) Schmidt, W. J. Chem. Phys. 1977, 66, 828.
73. (b) Dias, J. R. Handbook of Polycyclic Hydrocarbons Part A: Benzenoid Hydrocarbons; Elsevier: Amsterdam, 1987.
74. Forster, T. Angew. Chem., Int. Ed. Engl. 1969, 8, 333.
75. (a) Pregosin, P. S.; Kumar, P. G. A.; Fernandez, I. Chem. Rev. 2005, 105, 2977.
76. (b) Valentini, M.; Pregosin, P. S.; Ruegger, H. Organometallics 2000, 19, 2551.
77. H values for monomers of 1 and 3 as determined by X-ray were found to be 4.52 and 5.66 Å, respectively. These values are more in agreement than those calculated for the dimers, which have X-ray radii values of 6.22 and 7.45 Å, respectively.
78. Li, R.; Lim, E. C. J. Chem. Phys. 1972, 57, 605.
79. (a) Birks, J. B.; Christophorou, L. G. Nature 1962, 194, 442.
80. (b) Sasson, R.; Braitbart, O.; Weinreb, A. J. Lumin. 1988, 39, 223.
81. See, for example: (a) Inoue, M.; Ukon, M.; Watanabe, T.; Shimizu, Y.; Monobe, H. U.S. Patent 6733849, 2004.
82. (b) Okada, S.; Mizutani, H.; Tsuboyama, A.; Takiguchi, T.; Moriyama, T. U.S. Patent 6528940, 2003.
83. (c) Ishiskawa, H.; Toguchi, S.; Oda, A. U.S. Patent 6492041, 2002.
84. (d) Takiguchi, T.; Okada, S.; Tsuboyama, A.; Nakamura, S.; Moriyama, T. U.S. Patent 6491847, 2002.
85. (e) Paulus, W.; Haussling, L.; Siemensmeyer, K.; Etzbach, K. H.; Adam, D.; Simmerer, J.; Ringsdorf, H.; Schuhmacher, P.; Haarer, D.; Kumar. S. U.S. Patent 6036883, 2000.