Chiral J-aggregates of atropo-enantiomeric perylene bisimides and their self-sorting behavior

Chemistry - A European Journal

Volumn 18, Issue 23, 2012, Pages 7060-7070

  Xie, Zengqi ^a   Stepanenko, Vladimir ^a   Radacki, Krzysztof ^a   Würthner, Frank ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

chirality; helical nanowires; J aggregates; perylene bisimide; self assembly

Indexed keywords

AFM; ENANTIOPURE; HIGH IMPACT; HOMOCHIRAL; HOMOCHIRALITY; J AGGREGATES; LENGTH-TO-WIDTH RATIO; MOLECULAR STACKING; PERYLENE BISIMIDES; PHOTOLUMINESCENCE EFFICIENCY; SELF-RECOGNITION; SELF-SORTING; STEADY-STATE FLUORESCENCE;

AGGLOMERATION; ATOMIC FORCE MICROSCOPY; CHIRALITY; ENANTIOMERS; FLUORESCENCE SPECTROSCOPY; NANOWIRES; NUCLEATION; OPTICAL PROPERTIES; SELF ASSEMBLY;

AGGREGATES;

EID: 84861589641     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200089     Document Type: Article

References (96)

1. J-Aggregates, (Ed:, T. Kobayashi,), World Scientific, Singapore, 1996
2. D. Möbius, Adv. Mater. 1995, 7, 437-444
3. K. C. Hannah, B. A. Armitage, Acc. Chem. Res. 2004, 37, 845-853
4. S. Kirstein, S. Dähne, Int. J. Photoenergy 2006, 5, 3
5. F. C. Spano, Acc. Chem. Res. 2010, 43, 429-439
6. F. Würthner, T. E. Kaiser, C. R. Saha-Möller, Angew. Chem. 2011, 123, 3436-3473
7. Angew. Chem. Int. Ed. 2011, 50, 3376-3410.
8. K. E. Achyuthan, T. S. Bergstedt, L. Chen, R. M. Jones, S. Kumaraswamy, S. A. Kushon, K. D. Ley, L. Lu, D. McBranch, H. Mukundan, F. Rininsland, X. Shi, W. Xia, D. G. Whitten, J. Mater. Chem. 2005, 15, 2648-2656
9. D. G. Whitten, K. E. Achyuthan, G. P. Lopez, O. K. Kim, Pure Appl. Chem. 2006, 78, 2313-2323.
10. D. M. Eisele, H. V. Berlepsch, C. Böttcher, K. J. Stevenson, D. A. VandenBout, S. Kirstein, J. P. Rabe, J. Am. Chem. Soc. 2010, 132, 2104-2105.
11. E. Lang, A. Sorokin, M. Drechsler, Y. V. Malyukin, J. Köhler, Nano Lett. 2005, 5, 2635-2640
12. H. Lin, R. Camacho, Y. Tian, T. E. Kaiser, F. Würthner, I. G. Scheblykin, Nano Lett. 2010, 10, 620-626.
13. C. Spitz, S. Dähne, A. Ouart, H.-W. Abraham, J. Phys. Chem. B 2000, 104, 8664-8669
14. A. Chowdhury, S. Wachsmann-Hogiu, P. R. Bangal, I. Raheem, L. A. Peteanu, J. Phys. Chem. B 2001, 105, 12196-12201
15. O.-K. Kim, J. Je, G. Jernigan, L. Buckley, D. Whitten, J. Am. Chem. Soc. 2006, 128, 510-516
16. H. Görner, T. D. Slavnova, A. K. Chibisov, J. Phys. Chem. B 2010, 114, 9330-9337
17. T. D. Slavnova, H. Görner, A. K. Chibisov, J. Phys. Chem. B 2011, 115, 3379-3384.
18. O. Ohno, Y. Kaizu, H. Kobayashi, J. Chem. Phys. 1993, 99, 4128-4139
19. J. M. Ribõ, J. Crusats, F. Sagués, J. Claret, R. Rubires, Science 2001, 292, 2063-2066
20. A. S. R. Koti, N. Periasamy, Chem. Mater. 2003, 15, 369-371
21. R. Lauceri, G. F. Fasciglione, A. D'Urso, S. Marini, R. Purrello, M. Coletta, J. Am. Chem. Soc. 2008, 130, 10476-10477
22. A. Mammana, G. Pescitelli, T. Asakawa, S. Jockusch, A. G. Petrovic, R. R. Monaco, R. Purrello, N. J. Turro, K. Nakanishi, G. A. Ellestad, M. Balaz, N. Berova, Chem. Eur. J. 2009, 15, 11853-11866
23. A. D'Urso, A. Mammana, M. Balaz, A. E. Holmes, N. Berova, R. Lauceri, R. Purrello, J. Am. Chem. Soc. 2009, 131, 2046-2047
24. M. A. Castriciano, A. Roemo, G. DeLuca, V. Villari, L. M. Scolaro, N. Micali, J. Am. Chem. Soc. 2011, 133, 765-767.
25. T. S. Balaban, H. Tamiaki, A. R. Holzwarth, Top. Curr. Chem. 2005, 258, 1-38
26. V. Huber, M. Katterle, M. Lysetska, F. Würthner, Angew. Chem. 2005, 117, 3208-3212
27. Angew. Chem. Int. Ed. 2005, 44, 3147-3151
28. V. Huber, S. Sengupta, F. Würthner, Chem. Eur. J. 2008, 14, 7791-7807.
29. J.-S. Zhao, Y.-B. Ruan, R. Zhou, Y.-B. Jiang, Chem. Sci. 2011, 2, 937-944
30. F. Würthner, C. Bauer, V. Stepanenko, S. Yagai, Adv. Mater. 2008, 20, 1695-1698.
31. A. R. A. Palmans, E. W. Meijer, Angew. Chem. 2007, 119, 9106-9126
32. Angew. Chem. Int. Ed. 2007, 46, 8948-8968.
33. F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491-1546
34. D. B. Amabilino, J. Veciana, Top. Curr. Chem. 2006, 265, 253-302
35. M. R. Wasielewski, J. Org. Chem. 2006, 71, 5051-5066
36. A. Ajayaghosh, V. K. Praveen, Acc. Chem. Res. 2007, 40, 644-656
37. L. Zang, Y. Che, J. S. Moore, Acc. Chem. Res. 2008, 41, 1596-1608
38. D. González-Rodríguez, A. P. H. J. Schenning, Chem. Mater. 2011, 23, 310-325
39. F. S. Kim, G. Ren, S. A. Jenekhe, Chem. Mater. 2011, 23, 682-732
40. B. Rybtchinski, ACS Nano 2011, 5, 6791-6818.
41. J. H. KyHirschberg, L. Brunsveld, A. Ramzi, J. A. J. M. Vekemans, R. Sijbesma, E. W. Meijer, Nature 2000, 407, 167-170
42. J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, N. A. J. M. Sommerdijk, Chem. Rev. 2001, 101, 4039-4070
43. A. Ajayaghosh, P. Chithra, R. Varghese, Angew. Chem. 2007, 119, 234-237
44. Angew. Chem. Int. Ed. 2007, 46, 230-233
45. P. Chithra, R. Varghese, K. P. Divya, A. Ajayaghosh, Chem. Asian J. 2008, 3, 1365-1373
46. D. K. Smith, Chem. Soc. Rev. 2009, 38, 684-694
47. C. C. Lee, C. Grenier, E. W. Meijer, A. P. H. J. Schenning, Chem. Soc. Rev. 2009, 38, 671-683
48. Y. Hizume, K. Tashiro, R. Charvet, Y. Yamamoto, A. Saeki, S. Seki, T. Aida, J. Am. Chem. Soc. 2010, 132, 6628-6629
49. I. Danila, F. Riobé, F. Piron, J. Puigmartí-Luis, J. D. Wallis, M. Linares, H. Ågren, D. Beljonne, D. B. Amabilino, N. Avarvari, J. Am. Chem. Soc. 2011, 133, 8344-8353.
50. F. Würthner, Pure Appl. Chem. 2006, 78, 2341-2349;
51. A. C. Grimsdale, K. Müllen, Angew. Chem. 2005, 117, 5732-5772
52. Angew. Chem. Int. Ed. 2005, 44, 5592-5629.
53. P. Osswald, F. Würthner, J. Am. Chem. Soc. 2007, 129, 14319-14326.
54. P. Osswald, M. Reichert, G. Bringmann, F. Würthner, J. Org. Chem. 2007, 72, 3403-3411.
55. M. M. Safont-Sempere, G. Fernández, F. Würthner, Chem. Rev. 2011, 111, 5784-5814. For some most recent publications dedicated to self-sorting phenomena, see
56. M. Lista, J. Areephong, N. Sakai, S. Matile, J. Am. Chem. Soc. 2011, 133, 15228-15231
57. H. Maeda, K. Kinoshita, K. Naritani, Y. Bando, Chem. Commun. 2011, 47, 8241-8243
58. A. Das, S. Ghosh, Chem. Commun. 2011, 47, 8922-8924
59. K. Mahata, M. Schmittel, Beilstein J. Org. Chem. 2011, 7, 1555-1561
60. M. M. Smith, D. K. Smith, Soft Matter 2011, 7, 4856-4860
61. W. Jiang, D. Sattler, K. Rissanen, C. A. Schalley, Org. Lett. 2011, 13, 4502-4505
62. W. Jiang, Q. Wang, I. Linder, F. Klautzsch, C. A. Schalley, Chem. Eur. J. 2011, 17, 2344-2348.
63. M. M. Safont-Sempere, P. Osswald, M. Stolte, M. Grüne, M. Renz, M. Kaupp, K. Radacki, H. Braunschweig, F. Würthner, J. Am. Chem. Soc. 2011, 133, 9580-9591. For other examples of chiral self-sorting in π-aggregates, see
64. I. W. Hwang, T. Kamada, T. K. Ahn, D. M. Ko, T. Nakamura, A. Tsuda, A. Osuka, D. Kim, J. Am. Chem. Soc. 2004, 126, 16187-16198
65. T. Kamada, N. Aratani, T. Ikeda, N. Shibata, Y. Higuchi, A. Wakamiya, S. Yamaguchi, K. S. Kim, Z. S. Yoon, D. Kim, A. Osuka, J. Am. Chem. Soc. 2006, 128, 7670-7678
66. M. Mizumura, H. Shinokubo, A. Osuka, Angew. Chem. 2008, 120, 5458-5461
67. Angew. Chem. Int. Ed. 2008, 47, 5378-5381
68. T. Kaseyama, S. Furumi, X. Zhang, K. Tanaka, M. Takeuchi, Angew. Chem. 2011, 123, 3768-3771
69. Angew. Chem. Int. Ed. 2011, 50, 3684-3687.
70. Z. Xie, F. Würthner, Org. Lett. 2010, 12, 3204-3207.
71. Y. G. Zhen, W. Yue, Y. Li, W. Jiang, S. DiMotta, E. DiDonato, F. Negri, S. Ye, Z. H. Wang, Chem. Commun. 2010, 46, 6078-6080
72. H. L. Qian, F. Negri, C. R. Wang, Z. H. Wang, J. Am. Chem. Soc. 2008, 130, 17970-17976
73. H. L. Qian, Z. H. Wang, W. Yue, D. B. Zhu, J. Am. Chem. Soc. 2007, 129, 10664-10665.
74. T. E. Kaiser, H. Wang, V. Stepanenko, F. Würthner, Angew. Chem. 2007, 119, 5637-5640
75. Angew. Chem. Int. Ed. 2007, 46, 5541-5544
76. T. E. Kaiser, V. Stepanenko, F. Würthner, J. Am. Chem. Soc. 2009, 131, 6719-6732.
77. G. Sheldrick, Acta Crystallogr. 2008, A64, 112-122.
78. F. Würthner, A. Sautter, J. Schilling, J. Org. Chem. 2002, 67, 3037-3044.
79. F. C. DeSchryver, T. Vosch, M. Cotlet, M. VanderAuweraer, K. Müllen, J. Hofkens, Acc. Chem. Res. 2005, 38, 514-522.
80. P. Jonkheijm, P. vanderSchoot, A. P. H. J. Schenning, E. W. Meijer, Science 2006, 313, 80-83
81. M. M. J. Smulders, A. P. H. J. Schenning, E. W. Meijer, J. Am. Chem. Soc. 2008, 130, 606-611.
82. R. B. Martin, Chem. Rev. 1996, 96, 3043-3064.
83. C. A. Hunter, H. L. Anderson, Angew. Chem. 2009, 121, 7624-7636
84. Angew. Chem. Int. Ed. 2009, 48, 7488-7499 and references therein.
85. C. Huang, S. Barlow, S. R. Marder, J. Org. Chem. 2011, 76, 2386-2407
86. H. Langhals, Heterocycles 1995, 40, 477-500.
87. N. Harada, K. Nakanishi, Acc. Chem. Res. 1972, 5, 257-263
88. N. Berova, L. DiBari, G. Pescitelli, Chem. Soc. Rev. 2007, 36, 914-931.
89. Z. Chen, V. Stepanenko, V. Dehm, P. Prins, L. D. A. Siebbeles, J. Seibt, P. Marquetand, V. Engel, F. Würthner, Chem. Eur. J. 2007, 13, 436-449
90. Z. Chen, U. Baumeister, C. Tschierske, F. Würthner, Chem. Eur. J. 2007, 13, 450-465.
91. A. S. Davydov, Theory of Molecular Excitons, McGraw-Hill, New York, 1969
92. P. Dawson, J. Phys. Chem. Solids 1975, 36, 1401-1403.
93. Chirality at the Nanoscale, Nanoparticles, Surfaces, Materials and more, (Ed.:, D.B. Amabilino,), Wiley-VCH, Weinheim, 2009.
94. Z. Chen, M. G. Debije, T. Debaerdemaeker, P. Osswald, F. Würthner, ChemPhysChem 2004, 5, 137-140.
95. R. Gvishi, R. Reisfeld, Z. Burshtein, Chem. Phys. Lett. 1993, 213, 338-344
96. R. Sens, K. H. Drexhage, J. Lumin. 1981, 24-25, 709-712.