Applying the oligomer approach to luminescent conjugated organoboranes

Journal of the American Chemical Society

Volumn 133, Issue 23, 2011, Pages 8802-8805

  Chen, Pangkuan ^a   Lalancette, Roger A ^a   Jäkle, Frieder ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLSTANNANES; BATHOCHROMIC SHIFT; EMISSION DATA; EXTENDED CONJUGATION; LUMO ENERGY LEVELS; MONODISPERSE; SQUARE WAVE VOLTAMMETRY; SYNTHETIC PROCEDURES;

LUMINESCENCE;

OLIGOMERS;

ARYLSILANE; ARYLSTANNANE; BORANE DERIVATIVE; BROMOBORANE; FLUORENEBORANE; OLIGOMER; ORGANOBORANE POLYMER; POLYMER; SILANE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; CYCLIC POTENTIOMETRY; POTENTIOMETRY; QUANTUM CHEMISTRY; SQUARE WAVE VOLTAMMETRY;

EID: 79958786301     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja201436a     Document Type: Article

References (64)

1. Brook, M. A. Silicon in organic, organometallic, and polymer chemistry; Wiley-VCH: New York, 2000
2. Baumgartner, T.; Réau, R. Chem. Rev. 2006, 106, 4681-4727
3. Matsumi, N.; Chujo, Y. Polym. J. 2008, 40, 77-89
4. Elbing, M.; Bazan, G. C. Angew. Chem., Int. Ed. 2008, 47, 834-838
5. Jäkle, F. Chem. Rev. 2010, 110, 3985-4022
6. Recent examples: Sase, S.; Cho, Y.-S.; Kawachi, A.; Wakamiya, A.; Yamaguchi, S.; Tsuji, H.; Tamao, K. Organometallics 2008, 27, 5441-5445
7. Barrière, F.; Fabre, B.; Hao, E. H.; LeJeune, Z. M.; Hwang, E.; Garno, J. C.; Nesterov, E. E.; Vicente, M. G. H. Macromolecules 2009, 42, 2981-2987
8. Simon, Y. C.; Peterson, J. J.; Mangold, C.; Carter, K. R.; Coughlin, E. B. Macromolecules 2009, 42, 512-516
9. Dash, B. P.; Satapathy, R.; Gaillard, E. R.; Maguire, J. A.; Hosmane, N. S. J. Am. Chem. Soc. 2010, 132, 6578-6587
10. Yang, J. A.; Aschemeyer, S.; Martinez, H. P.; Trogler, W. C. Chem. Commun. 2010, 46, 6804-6806
11. Interrante, L. V.; Rathore, J. S. Dalton Trans. 2010, 39, 9193-9202
12. Smith, R. C.; Protasiewicz, J. D. J. Am. Chem. Soc. 2004, 126, 2268-2269
13. Jin, Z.; Lucht, B. L. J. Am. Chem. Soc. 2005, 127, 5586-5595
14. Wright, V. A.; Patrick, B. O.; Schneider, C.; Gates, D. P. J. Am. Chem. Soc. 2006, 128, 8836-8844
15. Romero-Nieto, C.; Merino, S.; Rodríguez-López, J.; Baumgartner, T. Chem.-Eur. J. 2009, 15, 4135-4145
16. Naka, K.; Nakahashi, A.; Chujo, Y. Macromolecules 2007, 40, 1372-1376
17. Matsumi, N.; Naka, K.; Chujo, Y. J. Am. Chem. Soc. 1998, 120, 5112-5113
18. Heilmann, J. B.; Scheibitz, M.; Qin, Y.; Sundararaman, A.; Jäkle, F.; Kretz, T.; Bolte, M.; Lerner, H.-W.; Holthausen, M. C.; Wagner, M. Angew. Chem., Int. Ed. 2006, 45, 920-925
19. Zhao, C.; Wakamiya, A.; Yamaguchi, S. Macromolecules 2007, 40, 3898-3900
20. Yamaguchi, I.; Choi, B. J.; Koizumi, T. A.; Kubota, K.; Yamamoto, T. Macromolecules 2007, 40, 438-443
21. Li, H.; Sundararaman, A.; Venkatasubbaiah, K.; Jäkle, F. J. Am. Chem. Soc. 2007, 129, 5792-5793
22. Lorbach, A.; Bolte, M.; Li, H.; Lerner, H.-W.; Holthausen, M. C.; Jäkle, F.; Wagner, M. Angew. Chem., Int. Ed. 2009, 48, 4584-4588
23. Li, H.; Sundararaman, A.; Pakkirisamy, T.; Venkatasubbaiah, K.; Schödel, F.; Jäkle, F. Macromolecules 2011, 44, 95-103
24. Miyata, M.; Chujo, Y. Polym. J. 2002, 34, 967-969
25. Sundararaman, A.; Victor, M.; Varughese, R.; Jäkle, F. J. Am. Chem. Soc. 2005, 127, 13748-13749
26. Bonifácio, V. D. B.; Morgado, J.; Scherf, U. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 2878-2883
27. Liu, W.; Pink, M.; Lee, D. J. Am. Chem. Soc. 2009, 131, 8703-8707
28. Li, H.; Jäkle, F. Angew. Chem., Int. Ed. 2009, 48, 2313-2316
29. Gabbaï, F. P. Angew. Chem., Int. Ed. 2003, 42, 2218-2221
30. Entwistle, C. D.; Marder, T. B. Chem. Mater. 2004, 16, 4574-4585
31. Yamaguchi, S.; Wakamiya, A. Pure Appl. Chem. 2006, 78, 1413-1424
32. Recent examples: Kobayashi, H.; Sato, N.; Ichikawa, Y.; Miyata, M.; Chujo, Y.; Matsuyama, T. Synth. Met. 2003, 135-136, 393-394
33. Hudson, Z. M.; Wang, S. Acc. Chem. Res. 2009, 42, 1584-1596
34. Mercier, L. G.; Piers, W. E.; Parvez, M. Angew. Chem., Int. Ed. 2009, 48, 6108-6111
35. Chai, J.; Wang, C.; Jia, L.; Pang, Y.; Graham, M.; Cheng, S. Z. D. Synth. Met. 2009, 159, 1443-1449
36. Reitzenstein, D.; Lambert, C. Macromolecules 2009, 42, 773-782
37. Weber, L.; Werner, V.; Fox, M. A.; Marder, T. B.; Schwedler, S.; Brockhinke, A.; Stammler, H. G.; Neumann, B. Dalton Trans. 2009, 1339-1351
38. Hoven, C. V.; Wang, H. P.; Elbing, M.; Garner, L.; Winkelhaus, D.; Bazan, G. C. Nat. Mater. 2010, 9, 249-252
39. Cataldo, S.; Fabiano, S.; Ferrante, F.; Previti, F.; Patanè, S.; Pignataro, B. Macromol. Rapid Commun. 2010, 31, 1281-1286
40. Proń, A.; Baumgarten, M.; Müllen, K. Org. Lett. 2010, 12, 4236-4239
41. Caruso, A.; Siegler, M. A.; Tovar, J. D. Angew. Chem., Int. Ed. 2010, 49, 4213-4217
42. Yamaguchi, S.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2000, 122, 6335-6336
43. Wade, C. R.; Broomsgrove, A. E. J.; Aldridge, S.; Gabbaï, F. P. Chem. Rev. 2010, 110, 3958-3984
44. Tanaka, K.; Yamanaka, S.; Ueda, K.; Takeda, S.; Yamabe, T. Synth. Met. 1987, 20, 333-345
45. Salzner, U.; Lagowski, J. B.; Pickup, P. G.; Poirier, R. A. Synth. Met. 1998, 96, 177-189
46. Cao, H.; Ma, J.; Zhang, G.; Jiang, Y. Macromolecules 2005, 38, 1123-1130
47. Nagai, A.; Murakami, T.; Nagata, Y.; Kokado, K.; Chujo, Y. Macromolecules 2009, 42, 7217-7220
48. Wegner, G.; Müllen, K., Eds. Electronic Materials: The Oligomer Approach; VCH: Weinheim, Germany, 1996.
49. Martin, R. E.; Diederich, F. Angew. Chem., Int. Ed. 1999, 38, 1350-1377
50. Geng, Y.; Trajkovska, A.; Katsis, D.; Ou, J. J.; Culligan, S. W.; Chen, S. H. J. Am. Chem. Soc. 2002, 124, 8337-8347
51. Jo, J.; Chi, C.; Höger, S.; Wegner, G.; Yoon, D. Y. Chem.-Eur. J. 2004, 10, 2681-2688
52. Dudek, S. P.; Pouderoijen, M.; Abbel, R.; Schenning, A. P. H. J.; Meijer, E. W. J. Am. Chem. Soc. 2005, 127, 11763-11768
53. Tour, J. M. Chem. Rev. 1996, 96, 537-553
54. Mishra, A.; Ma, C.-Q.; Bäuerle, P. Chem. Rev. 2009, 109, 1141-1276
55. Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 4960-4976
56. Ito, A.; Ino, H.; Tanaka, K.; Kanemoto, K.; Kato, T. J. Org. Chem. 2002, 67, 491-498
57. Keller, J. M.; Schanze, K. S. Organometallics 2009, 28, 4210-4216
58. Related studies on boronate polymers: Niu, W.; Smith, M. D.; Lavigne, J. J. J. Am. Chem. Soc. 2006, 128, 16466-16467
59. Qin, Y.; Kiburu, I.; Shah, S.; Jäkle, F. Macromolecules 2006, 39, 9041
60. For a discussion of the effects of bulky groups on these parameters, see: Li, H.; Jäkle, F. Polym. Chem. 2011, 2, 897-905
61. Schulz, A.; Kaim, W. Chem. Ber. 1989, 122, 1863-1868
62. Sundararaman, A.; Venkatasubbaiah, K.; Victor, M.; Zakharov, L. N.; Rheingold, A. L.; Jäkle, F. J. Am. Chem. Soc. 2006, 128, 16554-16565
63. Frisch, M. J. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
64. Meier, H. Angew. Chem., Int. Ed. 2005, 44, 2482-2506