Self-organization of hydrogen-bonding naphthalene chromophores into J-type nanorings and H-type nanorods: Impact of regioisomerism

Angewandte Chemie - International Edition

Volumn 51, Issue 27, 2012, Pages 6643-6647

  Yagai, Shiki ^a,c   Goto, Yusaku ^a   Lin, Xu ^a   Karatsu, Takashi ^a   Kitamura, Akihide ^a   Kuzuhara, Daiki ^b   Yamada, Hiroko ^b,c   Kikkawa, Yoshihiro ^d   Saeki, Akinori ^e   Seki, Shu ^e  

^a CHIBA UNIVERSITY   (Japan)

^b NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^d NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^e OSAKA UNIVERSITY   (Japan)

Author keywords

H aggregates; J aggregates; nanorings; self assembly; supramolecular chemistry

Indexed keywords

1D NANOSTRUCTURES; EXCITONIC COUPLING; EXCITONIC INTERACTION; H-AGGREGATES; J AGGREGATES; REGIOISOMERISM; REGIOISOMERS; SELF-ASSEMBLING;

AGGREGATES; CHROMOPHORES; CRYSTALLINE MATERIALS; HYDROGEN; NANORODS; NANOSTRUCTURED MATERIALS; NAPHTHALENE; SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY;

NANORINGS;

EID: 84863223000     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201201436     Document Type: Article

References (47)

1. T. Kondo, K. Yoshida, A. Nakagawa, T. Kawai, H. Tamura, T. Goto, Nature 1992, 358, 515-518
2. G. McDermott, S. M. Prince, A. A. Freer, A. M. Hawthornthwaite-Lawless, M. Z. Papiz, R. J. Cogdell, N. W. Isaacs, Nature 1995, 374, 517-521.
3. X. Hu, A. Damjanovic, T. Ritz, K. Schulten, Proc. Natl. Acad. Sci. USA 1998, 95, 5935-5941.
4. A. M. van Oijen, M. Ketelaars, J. Kohler, T. J. Aartsma, J. Schmidt, Science 1999, 285, 400-402.
5. G. Scheibe, Angew. Chem. 1936, 49, 563
6. E. E. Jelley, Nature 1936, 138, 1009-1010
7. J-Aggregates (Ed.:, T. Kobayashi,), World Scientific, Singapore, 1996.
8. L. Schmidt-Mende, A. Fechtenkotter, K. Müllen, E. Moons, R. H. Friend, J. D. MacKenzie, Science 2001, 293, 1119-1122
9. A. M. van de Craats, J. M. Warman, K. Müllen, Y. Geerts, J. D. Brand, Adv. Mater. 1998, 10, 36-38
10. J. Wu, W. Pisula, K. Müllen, Chem. Rev. 2007, 107, 718-747
11. F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491-1546
12. Z. Chen, A. Lohr, C. R. Saha-Moller, F. Würthner, Chem. Soc. Rev. 2009, 38, 564-584.
13. B. M. Rosen, C. J. Wilson, D. A. Wilson, M. Peterca, M. R. Imam, V. Percec, Chem. Rev. 2009, 109, 6275-6540
14. T. Nakanishi, Chem. Commun. 2010, 46, 3425-3436.
15. S. Yagai, S. Kubota, H. Saito, K. Unoike, T. Karatsu, A. Kitamura, A. Ajayaghosh, M. Kanesato, Y. Kikkawa, J. Am. Chem. Soc. 2009, 131, 5408-5410
16. S. Yagai, T. Kinoshita, Y. Kikkawa, T. Karatsu, A. Kitamura, Y. Honsho, S. Seki, Chem. Eur. J. 2009, 15, 9320-9324
17. S. Yagai, Y. Goto, T. Karatsu, A. Kitamura, Y. Kikkawa, Chem. Eur. J. 2011, 17, 13657-13660.
18. J.-K. Kim, E. Lee, Z. Huang, M. Lee, J. Am. Chem. Soc. 2006, 128, 14022-14023
19. S. Yagai, S. Mahesh, Y. Kikkawa, K. Unoike, T. Karatsu, A. Kitamura, A. Ajayaghosh, Angew. Chem. 2008, 120, 4769-4772
20. Angew. Chem. Int. Ed. 2008, 47, 4691-4694
21. S. Yagai, H. Aonuma, Y. Kikkawa, S. Kubota, T. Karatsu, A. Kitamura, S. Mahesh, A. Ajayaghosh, Chem. Eur. J. 2010, 16, 8652-8661
22. H. Shao, J. Seifert, N. C. Romano, M. Gao, J. J. Helmus, C. P. Jaroniec, D. A. Modarelli, J. R. Parquette, Angew. Chem. 2010, 122, 7854-7857
23. Angew. Chem. Int. Ed. 2010, 49, 7688-7691.
24. F. Würthner, T. E. Kaiser, C. R. Saha-Möller, Angew. Chem. 2011, 123, 3436-3473
25. Angew. Chem. Int. Ed. 2011, 50, 3376-3410
26. G. Borzsonyi, R. L. Beingessner, T. Yamazaki, J.-Y. Cho, A. J. Myles, M. Malac, R. Egerton, M. Kawasaki, K. Ishizuka, A. Kovalenko, H. Fenniri, J. Am. Chem. Soc. 2010, 132, 15136-15139.
27. U. Rösch, S. Yao, R. Wortmann, F. Würthner, Angew. Chem. 2006, 118, 7184-7188
28. Angew. Chem. Int. Ed. 2006, 45, 7026-7030.
29. M. Kasha, H. R. Rawls, M. A. El-Bayoumi, Pure Appl. Chem. 1965, 11, 371-392.
30. Y. Hong, J. W. Y. Lam, B. Z. Tang, Chem. Soc. Rev. 2011, 40, 5361-5388.
31. H. J. Butt, R. Guckenberger, J. P. Rabe, Ultramicroscopy 1992, 46, 375-393
32. P. Samorí, V. Francke, T. Mangel, K. Müllen, J. P. Rabe, Opt. Mater. 1998, 9, 390-393.
33. T. Kato, N. Mizoshita, K. Kishimoto, Angew. Chem. 2006, 118, 44-74
34. Angew. Chem. Int. Ed. 2006, 45, 38-68.
35. C. Destrade, P. Foucher, H. Gasparoux, T. Nguyen Huu, A. M. Levelut, J. Malthete, Mol. Cryst. Liq. Cryst. 1984, 106, 121-146.
36. K. Hatsusaka, K. Ohta, I. Yamamoto, H. Shirai, J. Mater. Chem. 2001, 11, 423-433.
37. G. Ungar, V. Percec, M. N. Holerca, G. Johansson, J. A. Heck, Chem. Eur. J. 2000, 6, 1258-1266.
38. S. Jin, Y. Ma, S. C. Zimmerman, S. Z. D. Cheng, Chem. Mater. 2004, 16, 2975-2977
39. S. Yagai, T. Nakajima, K. Kishikawa, S. Kohmoto, T. Karatsu, A. Kitamura, J. Am. Chem. Soc. 2005, 127, 11134-11139.
40. C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534.
41. M. Peterca, V. Percec, M. R. Imam, P. Leowanawat, K. Morimitsu, P. A. Heiney, J. Am. Chem. Soc. 2008, 130, 14840-14852.
42. V. Percec, M. Glodde, T. K. Bera, Y. Miura, I. Shiyanovskaya, K. D. Singer, V. S. K. Balagurusamy, P. A. Heiney, I. Schnell, A. Rapp, H. W. Spiess, S. D. Hudson, H. Duan, Nature 2002, 417, 384-387.
43. F. C. Grozema, L. D. A. Siebbeles, J. M. Warman, S. Seki, S. Tagawa, U. Scherf, Adv. Mater. 2002, 14, 228-231
44. A. Acharya, S. Seki, A. Saeki, Y. Koizumi, S. Tagawa, Chem. Phys. Lett. 2005, 404, 356-360
45. T. Amaya, S. Seki, T. Moriuchi, K. Nakamoto, T. Nakata, H. Sakane, A. Saeki, S. Tagawa, T. Hirao, J. Am. Chem. Soc. 2009, 131, 408-409.
46. S. Yagai, Y. Nakano, S. Seki, A. Asano, T. Okubo, T. Isoshima, T. Karatsu, A. Kitamura, Y. Kikkawa, Angew. Chem. 2010, 122, 10186-10190
47. Angew. Chem. Int. Ed. 2010, 49, 9990-9994.