Charge-transfer interactions in tris-donor-tris-acceptor hexaarylbenzene redox chromophores

Chemistry - A European Journal

Volumn 18, Issue 38, 2012, Pages 11937-11948

  Steeger, Markus ^a   Lambert, Christoph ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

boranes; charge transfer; chromophores; donor acceptor systems; symmetry

Indexed keywords

ARYL SUBSTITUENTS; BORANES; C-V MEASUREMENT; CHARGE TRANSFER INTERACTION; CHARGE TRANSFER STATE; CYCLOTRIMERIZATION; CYCLOVOLTAMMETRY; DONOR-ACCEPTOR INTERACTION; DONOR-ACCEPTOR PAIRS; DONOR-ACCEPTOR SYSTEM; DONOR-ACCEPTORS; ELECTRON DONORS; ELECTRON-ACCEPTOR; ELECTRONIC COUPLING; FLUORESCENCE LIFETIMES; FLUORESCENCE SPECTRA; FLUORIDE ANIONS; FLUORIDE ION; HYDROGEN BONDING INTERACTIONS; ION-PAIRING; MIXED VALENCE; OXIDATION PEAK; PHOTOPHYSICAL PROPERTIES; REDOX CENTERS; REDUCTION PEAK; SHIELDING EFFECT; SYMMETRY-BREAKING; TRIARYLAMINES; TRIARYLBORANES; WATER MOLECULE;

BORON; BORON COMPOUNDS; CHARGE TRANSFER; COBALT; COBALT COMPOUNDS; CRYSTAL SYMMETRY; ELECTROMAGNETIC WAVE ABSORPTION; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; HYDROGEN BONDS; IONS; ORGANIC POLYMERS; PHOTOEXCITATION; SEPARATION; SUBSTITUTION REACTIONS;

CHROMOPHORES;

EID: 84866239462     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201104020     Document Type: Article

References (103)

1. C. Lambert, Angew. Chem. 2005, 117, 7503-7505
2. Angew. Chem. Int. Ed. 2005, 44, 7337-7339.
3. P. A. Liddell, G. Kodis, L. dea Laa Garza, A. L. Moore, T. A. Moore, D. Gust, J. Phys. Chem. B 2004, 108, 10256-10265
4. H. S. Cho, H. Rhee, J. K. Song, C.-K. Min, M. Takase, N. Aratani, S. Cho, A. Osuka, T. Joo, D. Kim, J. Am. Chem. Soc. 2003, 125, 5849-5860.
5. G. Kodis, Y. Terazono, P. A. Liddell, J. Andreasson, V. Garg, M. Hambourger, T. A. Moore, A. L. Moore, D. Gust, J. Am. Chem. Soc. 2006, 128, 1818-1827.
6. X. Hu, K. Schulten, Phys. Today 1997, 50, 28-34.
7. A. E. Keirstead, J. W. Bridgewater, Y. Terazono, G. Kodis, S. Straight, P. A. Liddell, A. L. Moore, T. A. Moore, D. Gust, J. Am. Chem. Soc. 2010, 132, 6588-6595.
8. D. Rausch, C. Lambert, Org. Lett. 2006, 8, 5037-5040.
9. D. Sun, S. V. Rosokha, J. K. Kochi, Angew. Chem. 2005, 117, 5263-5266
10. Angew. Chem. Int. Ed. 2005, 44, 5133-5136
11. V. J. Chebny, R. Shukla, R. Rathore, J. Phys. Chem. A 2006, 110, 13003-13006
12. C. Lambert, G. Nöll, Chem. Eur. J. 2002, 8, 3467-3477
13. S. V. Rosokha, I. S. Neretin, D. Sun, J. K. Kochi, J. Am. Chem. Soc. 2006, 128, 9394-9407
14. V. J. Chebny, D. Dhar, S. V. Lindeman, R. Rathore, Org. Lett. 2006, 8, 5041-5044
15. B. Traber, J. J. Wolff, F. Rominger, T. Oeser, R. Gleiter, M. Goebel, R. Wortmann, Chem. Eur. J. 2004, 10, 1227-1238
16. R. Rathore, C. L. Burns, S. A. Abdelwahed, Org. Lett. 2004, 6, 1689-1692
17. R. Rathore, C. L. Burns, M. I. Deselnicu, Org. Lett. 2001, 3, 2887-2890.
18. L. Jiménez-García, A. Kaltbeitzel, V. Enkelmann, J. S. Gutmann, M. Klapper, K. Müllen, Adv. Funct. Mater. 2011, 21, 2216-2224.
19. L. Zhi, K. Mullen, J. Mater. Chem. 2008, 18, 1472-1484.
20. R. Stahl, C. Lambert, C. Kaiser, R. Wortmann, R. Jakober, Chem. Eur. J. 2006, 12, 2358-2370.
21. S. Amthor, B. Noller, C. Lambert, Chem. Phys. 2005, 316, 141-152.
22. C. Lambert, G. Nöll, J. Schelter, Nat. Mater. 2002, 1, 69-73
23. C. Lambert, G. Nöll, J. Chem. Soc. Perkin Trans. 2 2002, 2039-2043
24. A. Heckmann, S. Amthor, C. Lambert, Chem. Commun. 2006, 2959-2961
25. K. Y. Law, Chem. Rev. 1993, 93, 449-486
26. S. Jungermann, N. Riegel, D. Müller, K. Meerholz, O. Nuyken, Macromolecules 2006, 39, 8911-8919
27. O. Nuyken, S. Jungermann, V. Wiederhirn, E. Bacher, K. Meerholz, Monatsh. Chem. 2006, 137, 811-824
28. H. Zhao, C. Tanjutco, S. Thayumanavan, Tetrahedron Lett. 2001, 42, 4421-4424
29. Y. Shirota, H. Kageyama, Chem. Rev. 2007, 107, 953-1010
30. Z. Ning, H. Tian, Chem. Commun. 2009, 5483-5495
31. M. Thelakkat, Macromol. Mater. Eng. 2002, 287, 442-461.
32. G. Zhou, C.-L. Ho, W.-Y. Wong, Q. Wang, D. Ma, L. Wang, Z. Lin, T. B. Marder, A. Beeby, Adv. Funct. Mater. 2008, 18, 499-511
33. T. Noda, Y. Shirota, J. Lumin. 2000, 87-89, 1168-1170
34. T. Noda, Y. Shirota, J. Am. Chem. Soc. 1998, 120, 9714-9715
35. H. Doi, M. Kinoshita, K. Okumoto, Y. Shirota, Chem. Mater. 2003, 15, 1080-1089
36. S. Yamaguchi, A. Wakamiya, Pure Appl. Chem. 2006, 78, 1413-1424.
37. C. H. Zhao, E. Sakuda, A. Wakamiya, S. Yamaguchi, Chem. Eur. J. 2009, 15, 10603-10612
38. Z. M. Hudson, S. N. Wang, Acc. Chem. Res. 2009, 42, 1584-1596
39. S. Yamaguchi, T. Shirasaka, K. Tamao, Org. Lett. 2000, 2, 4129-4132
40. D.-R. Bai, X.-Y. Liu, S. Wang, Chem. Eur. J. 2007, 13, 5713-5723
41. D. Reitzenstein, C. Lambert, Macromolecules 2009, 42, 773-782
42. Z. Yuan, J. C. Collings, N. J. Taylor, T. B. Marder, C. Jardin, J.-F. Halet, J. Solid State Chem. 2000, 154, 5-12
43. W.-L. Jia, D. Song, S. Wang, J. Org. Chem. 2003, 68, 701-705
44. Z.-Q. Liu, Q. Fang, D. Wang, D.-X. Cao, G. Xue, W.-T. Yu, H. Lei, Chem. Eur. J. 2003, 9, 5074-5084
45. Y. Sun, S. N. Wang, Inorg. Chem. 2010, 49, 4394-4404
46. S. B. Zhao, P. Wucher, Z. M. Hudson, T. M. McCormick, X. Y. Liu, S. N. Wang, X. D. Feng, Z. H. Lu, Organometallics 2008, 27, 6446-6456
47. F. Jäkle, Chem. Rev. 2010, 110, 3985-4022
48. J. B. Heilmann, M. Scheibitz, Y. Qin, A. Sundararaman, F. Jäkle, T. Kretz, M. Bolte, H.-W. Lerner, M. C. Holthausen, M. Wagner, Angew. Chem. 2006, 118, 934-939
49. Angew. Chem. Int. Ed. 2006, 45, 920-925.
50. Z. Yuan, N. J. Taylor, T. B. Marder, I. D. Williams, S. K. Kurtz, L. T. Cheng, J. Chem. Soc. Chem. Commun. 1990, 1489-1492
51. Z. Yuan, N. J. Taylor, Y. Sun, T. B. Marder, I. D. Williams, L.-T. Cheng, J. Organomet. Chem. 1993, 449, 27-37
52. Z. Yuan, C. D. Entwistle, J. C. Collings, D. Albesa-Jove, A. S. Batsanov, J. A. K. Howard, N. J. Taylor, H. M. Kaiser, D. E. Kaufmann, S.-Y. Poon, W.-Y. Wong, C. Jardin, S. Fathallah, A. Boucekkine, J.-F. Halet, T. B. Marder, Chem. Eur. J. 2006, 12, 2758-2771
53. M. Lequan, R. M. Lequan, K. C. Ching, J. Mater. Chem. 1991, 1, 997-999
54. Z. Yuan, N. J. Taylor, R. Ramachandran, T. B. Marder, Appl. Organomet. Chem. 1996, 10, 305-316
55. C. D. Entwistle, T. B. Marder, Chem. Mater. 2004, 16, 4574-4585
56. M. Lequan, R. M. Lequan, K. C. Ching, M. Barzoukas, A. Fort, H. Lahoucine, G. Bravic, D. Chasseau, J. Gaultier, J. Mater. Chem. 1992, 2, 719-725
57. M. Charlot, L. Porres, C. D. Entwistle, A. Beeby, T. B. Marder, M. Blanchard-Desce, Phys. Chem. Chem. Phys. 2005, 7, 600-606
58. Y. Liu, X. Xu, F. K. Zheng, Y. Cui, Angew. Chem. 2008, 120, 4614-4617
59. Angew. Chem. Int. Ed. 2008, 47, 4538-4541
60. J. C. Collings, S. Y. Poon, C. Lea Droumaguet, M. Charlot, C. Katan, L. O. Palsson, A. Beeby, J. A. Mosely, H. M. Kaiser, D. Kaufmann, W. Y. Wong, M. Blanchard-Desce, T. B. Marder, Chem. Eur. J. 2009, 15, 198-208
61. C. D. Entwistle, J. C. Collings, A. Steffen, L.-O. Palsson, A. Beeby, D. Albesa-Jove, J. M. Burke, A. S. Batsanov, J. A. K. Howard, J. A. Mosely, S.-Y. Poon, W.-Y. Wong, F. Ibersiene, S. Fathallah, A. Boucekkine, J.-F. Halet, T. B. Marder, J. Mater. Chem. 2009, 19, 7532-7544.
62. A. Pron', M. Baumgarten, K. Müllen, Org. Lett. 2010, 12, 4236-4239
63. C. R. Wade, A. E. J. Broomsgrove, S. Aldridge, F. P. Gabbai, Chem. Rev. 2010, 110, 3958-3984
64. A. Pron', G. Zhou, H. Norouzi-Arasi, M. Baumgarten, K. Müllen, Org. Lett. 2009, 11, 3550-3553
65. G. Zhou, M. Baumgarten, K. Müllen, J. Am. Chem. Soc. 2008, 130, 12477-12484
66. H. C. Schmidt, L. G. Reuter, J. Hamacek, O. S. Wenger, J. Org. Chem. 2011, 76, 9081-9085.
67. T. W. Hudnall, F. P. Gabbai, J. Am. Chem. Soc. 2007, 129, 11978-11986
68. C. W. Chiu, F. P. Gabbai, Dalton Trans. 2008, 814-817
69. T. Agou, M. Sekine, J. Kobayashi, T. Kawashima, J. Organomet. Chem. 2009, 694, 3833-3836
70. J. O. Huh, Y. Do, M. H. Lee, Organometallics 2008, 27, 1022-1025
71. C. R. Wade, F. P. Gabbai, Inorg. Chem. 2010, 49, 714-720.
72. U. Megerle, F. Selmaier, C. Lambert, E. Riedle, S. Lochbrunner, Phys. Chem. Chem. Phys. 2008, 10, 6245-6251
73. U. Megerle, C. Lambert, E. Riedle, S. Lochbrunner, Springer Ser. Chem. Phys. 2009, 92, 316-318.
74. C. D. Entwistle, T. B. Marder, Angew. Chem. 2002, 114, 3051-3056
75. Angew. Chem. Int. Ed. 2002, 41, 2927-2931
76. J. C. Doty, B. Babb, P. J. Grisdale, M. Glogowski, J. L. R. Williams, J. Organomet. Chem. 1972, 38, 229-236
77. W. Kaim, A. Schulz, Angew. Chem. 1984, 96, 611-612
78. Angew. Chem. Int. Ed. Engl. 1984, 23, 615-616.
79. A. Heckmann, C. Lambert, Angew. Chem. 2012, 124, 334-404.
80. C. Ester, A. Maderna, H. Pritzkow, W. Siebert, Eur. J. Inorg. Chem. 2000, 2000, 1177-1184.
81. N. E. Schore, Chem. Rev. 1988, 88, 1081-1119.
82. A. Steffen, R. M. Ward, W. D. Jones, T. B. Marder, Coord. Chem. Rev. 2010, 254, 1950-1976.
83. H. Kiesele, Anal. Chem. 1981, 53, 1952-1954.
84. A. Heckmann, C. Lambert, J. Am. Chem. Soc. 2007, 129, 5515-5527
85. A. Schulz, W. Kaim, Chem. Ber. 1989, 122, 1863-1868.
86. F. Barrière, W. E. Geiger, J. Am. Chem. Soc. 2006, 128, 3980-3989.
87. J. C. Curtis, J. A. Roberts, R. L. Blackbourn, Y. H. Dong, M. Massum, C. S. Johnson, J. T. Hupp, Inorg. Chem. 1991, 30, 3856-3860.
88. M. S. Yuan, Z. Q. Liu, Q. Fang, J. Org. Chem. 2007, 72, 7915-7922.
89. S. J. Strickler, R. A. Berg, J. Chem. Phys. 1962, 37, 814-822.
90. J. Fiedler, S. Zalis, A. Klein, F. M. Hornung, W. Kaim, Inorg. Chem. 1996, 35, 3039-3043.
91. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Kluwer Academic/Plenum, New York, 1999
92. R. D. Hall, B. Valeur, G. Weber, Chem. Phys. Lett. 1985, 116, 202-205.
93. W. Verbouwe, M. Vana dera Auweraer, F. C. Dea Schryver, J. J. Piet, J. M. Warman, J. Am. Chem. Soc. 1998, 120, 1319-1324
94. A. A. Demidov, D. L. Andrews, Photochem. Photobiol. 1996, 63, 39-52.
95. H. Sohn, S. Letant, M. J. Sailor, W. C. Trogler, J. Am. Chem. Soc. 2000, 122, 5399-5400
96. S. W. Zhang, T. M. Swager, J. Am. Chem. Soc. 2003, 125, 3420-3421.
97. Y. L. Rao, H. Amarne, S. B. Zhao, T. M. McCormick, S. Martic, Y. Sun, R. Y. Wang, S. N. Wang, J. Am. Chem. Soc. 2008, 130, 12898-12900.
98. R. J. LeSuer, C. Buttolph, W. E. Geiger, Anal. Chem. 2004, 76, 6395-6401.
99. S. Santi, L. Orian, C. Durante, E. Z. Bencze, A. Bisello, A. Donoli, A. Ceccon, F. Benetollo, L. Crociani, Chem. Eur. J. 2007, 13, 7933-7947.
100. W. H. Melhuish, J. Phys. Chem. 1961, 65, 229-235.
101. P. Gans, A. Sabatini, A. Vacca, Talanta 1996, 43, 1739-1753.
102. R. C. Dorfman, Y. Lin, M. D. Fayer, J. Phys. Chem. 1989, 93, 6388-6396.
103. K. A. Connors, Binding Constants, Wiley, New York, 1987, p. 78.