Self-assembly of m-diethynylbenzene macrocycles containing exoannular chiral side chains

Advanced Functional Materials

Volumn 16, Issue 12, 2006, Pages 1549-1554

  Tobe, Yoshito ^a   Nagai, Toshiro ^a   Araki, Shunji ^a   Ichikawa, Tomoyuki ^a   Nomoto, Akihiro ^b   Sonoda, Motohiro ^a   Hirose, Keiji ^a  

^a OSAKA UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATES; ATOMIC FORCE MICROSCOPY; FILMS; ISOMERS; METHANOL; QUARTZ; SELF ASSEMBLY; SOLVENTS; SUBSTRATES;

CHLOROFORM; DIETHYNYLBENZENE; SIDE CHAINS (AROMATIC COMPOUNDS); SOLID FILMS;

AROMATIC COMPOUNDS;

EID: 33747602993     PISSN: 1616301X     EISSN: 16163028     Source Type: Journal    
DOI: 10.1002/adfm.200500306     Document Type: Article

References (56)

1. a) R. Fiesel, D. Neher, U. Scherf, Synth. Met. 1999, 102, 1457.
2. b) M. Oda, S. C. J. Meskers, H. G. Nothofer, U. Scherf, D. Neher, Synth. Met. 2000, 111-112, 575.
3. c) M. Oda, H. G. Nothofer, G. Lieser, U. Scherf, S. C. J. Meskers, D. Neher, Adv. Mater. 2000, 12, 362.
4. a) M. M. Bouman, E. E. Havinga, R. A. J. Janssen, E. W. Meijer, Mol. Cryst. Liq. Cryst. 1994, 256, 439.
5. b) M. M. Bouman, E. W. Meijer, Adv. Mater. 1995, 7, 385.
6. c) A. F. M. Kilbinger, A. P. H. J. Schenning, F. Goldoni, W. J. Feast, E. W. Meijer, J. Am. Chem. Soc. 2000, 122, 1820.
7. d). A. P. H. J. Schenning, A. F. M. Kilbinger, F. Biscarini, M. Cavallini, H. J. Cooper, P. J. Derrick, W. J. Feast, R. Lazzaroni, Ph. Leclère, L. A. McDonell, E. W. Meijer, S. C. Meskers, J. Am. Chem. Soc. 2002, 124, 1269.
8. e) D. Iarossi, A. Mucci, F. Parenti, L. Schenetti, R. Seeber, C. Zanardi, A. Forni, M. Tonelli, Chem. Eur. J. 2001, 7, 676.
9. A. F. Drake, P. Udvarhelyi, D. J. Ando, D. Bloor, J. & Obhi, S. Mann, Polymer 1989, 30, 1063.
10. E. Peeters, A. Delmotte, R. A. J. Janssen, E. W. Meijer, Adv. Mater. 1997, 9, 493.
11. a) R. Fiesel, U. Scherf, Macromol. Rapid Commun. 1998, 19, 427.
12. b) R. Fiesel, C. E. Halkyard, M. E. Rampey, L. Kloppenburg, S. L. Studer-Martinez, U. Scherf, U. H. F. Bunz, Macromol. Rapid Commun. 1999, 20, 107.
13. c) J. N. Wilson, W. Steffen, T. G. McKenzie, G. Lieser, M. Oda, D. Neher, U. H. F. Bunz, J. Am. Chem. Soc. 2002, 124, 6830.
14. S. Zahn, T. M. Swager, Angew. Chem. Int. Ed. 2002, 41, 4266.
15. a) R. B. Prince, L. Bruns, E. W. Meijer, J. S. Moore, Angew. Chem. Int. Ed. 2000, 39, 228.
16. b) R. B. Prince, J. S. Moore, L. Brunsveld, E. W. Meijer, Chem. Eur. J. 2001, 7, 4150.
17. c) L. Brunsveld, E. W. Meijer, R. B. Prince, J. S. Moore, J. Am. Chem. Soc. 2001, 123, 7978.
18. L. Brunsveld, R. B. Prince, E. W. Meijer, J. S. Moore, Org. Lett. 2000, 2, 1525.
19. a) V. Král, F. P. Schmidtchen, K. Lang, M. Berger, Org. Lett. 2002, 4, 51.
20. b) A. Fechtenkötter, N. Tchebotareva, M. Watson, K. Müllen, Tetrahedron 2001, 57, 3769.
21. c) N. Kobayashi, W. A. Nevin, Chem. Lett. 1998, 851.
22. d). M. M. Green, H. Ringsdorf, J. Wagner, R. Wüstefeld, Angew. Chem. Int. Ed. Engl. 1990, 29, 1478.
23. e) C. F. van Nostrum, A. W. Bosman, G. H. Gelinck, P. G. Schouten, J. M. Warman, A. P. M. Kentgens, M. A. C. Devillers, A. Meijerink, S. J. Picken, U. Sohling, A.-J. Schouten, R. J. M. Nolte, Chem. Eur. J. 1995, 1, 171.
24. f) M. L. Bushey, A. Hwang, P. C. W. Stephens, C. Nuckolls, Angew. Chem. Int. Ed. 2002, 41, 2828.
25. a) G. Gottarelli, E. Mezzina, G. P. Spada, F. Carsughi, G. Di Nicola, P. Mariani, A. Sabatucci, S. Bonazzi, Helv. Chim. Acta 1996, 79, 220.
26. b) A. R. A. Palmans, J. A. J. M. Vekemans, E. E. Havinga, E. W. Meijer, Angew. Chem. Int. Ed. Engl. 1997, 36, 2648.
27. c) L. Brunsveld, H. Zhang, M. Glasbeek, J. A. J. M. Vekemans, E. W. Meijer, J. Am. Chem. Soc. 2000, 122, 6175.
28. J. J. van Gorp, J. A. J. M. Vekemans, E. W. Meijer, J. Am. Chem. Soc. 2002, 124, 14 759.
29. M. M. Green, Circular Dichroism, Principles and Applications, 2nd ed. (Eds: N. Berova, K. Nakanishi, R. W. Woody), Wiley, New York 2000, pp. 491-520.
30. For reviews on shape-persistent macrocycles: a) J. S. Moore, Acc. Chem. Res. 1997, 30, 402.
31. b) D. Zhao, J. S. Moore, Chem. Commun. 2003, 807.
32. c) S. Höger, J. Polym. Sci. Part A 1999, 37, 2685.
33. d). S. Höger, Chem. Eur. J. 2004, 10, 1320.
34. e) C. Grave, A. D. Schlüter, Eur. J. Org. Chem. 2002, 3075.
35. f) S. Höger, Acetylene Chemistry (Eds: F. Diederich, P. J. Stang, R. R. Tykwinski), Wiley-VCH, Weinheim, Germany 2005, pp. 427-452.
36. For self-association of diethynylbenzene macrocycles: a) Y. Tobe, N. Utsumi, K. Kawabata, K. Naemura, Tetrahedron Lett. 1996, 37, 9325.
37. b) Y. Tobe, N. Utsumi, A. Nagano, K. Naemura, Angew. Chem. Int. Ed. 1998, 37, 1285.
38. c) Y. Tobe, A. Nagano, K. Kawabata, M. Sonoda, K. Naemura, Org. Lett. 2000, 2, 3265.
39. Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Adachi, S. Araki, M. Sonoda, K. Hirose, K. Naemura, J. Am. Chem. Soc. 2002, 124, 5350.
40. Self-association behavior of phenylacetylene macrocycles has also been studied in detail by Moore and co-workers: a) J. Zhang, J. S. Moore, J. Am. Chem. Soc. 1992, 114, 9701.
41. b) A. S. Shetty, J. Zhang, J. S. Moore, J. Am. Chem. Soc. 1996, 118, 1019.
42. c) S. Lahiri, J. L. Thompson, J. S. Moore, J. Am. Chem. Soc. 2000, 122, 11 315.
43. a) K. Nakamura, H. Okubo, M. Yamaguchi, Org. Lett. 2001, 3, 1097.
44. b) Y. Saiki, K. Nakamura, Y. Nigorikawa, M. Yamaguchi, Angew. Chem. Int. Ed. 2003, 42, 5190.
45. c) Y. Saiki, H. Sugiura, K. Nakamura, M. Yamaguchi, T. Hoshi, J. Anzai, J. Am. Chem. Soc. 2003, 125, 9268.
46. The preparation of chiral alcohols (S)-4 and (R)-4 was reported in the Supporting Information of a previous publication [6a]. We prepared them by essentially the same route but with different procedures.
47. Though we also attempted to observe chiral solvent-induced CD of achiral 1 in chiral polar solvents such as (S)-butanol/chloroform (9:1), (S)-2,3-propanediol/chloroform (5:5), (R)-1-chlorc-1,2-propanediol, and (R)-ethyl lactate/chloroform (9:1), which may interact with the polar side chain of 1, no induced CD was observed.
48. The CD spectra did not change by rotating the quartz plate by 90° with respect to the light path, thus excluding the possibility of linear dichroism.
49. The same solvent-dependent CD signals were observed when an untreated slide glass, instead of a quartz glass, was used.
50. Attempted X-ray diffraction measurement was not successful presumably because the solid films were too thin or the degree of ordered structures was low. Collection of the solid on the quartz substrates by scraping the films with a spatula caused coloration of the solid.
51. 1HNMR spectrum. Since the NMR spectrum did not exhibit a methanol signal, the possibility of its participation in the aggregate formation can be excluded.
52. For examples of hierarchically ordered aggregates of achiral porphyrin derivatives on the surfaces: a) L. Latterini, R. Blossey, J. Hofkens, P. Vanoppen, F. C. De Schryver, A. E. Rowan, R. J. M. Nolte, Langmuir 1999, 15, 3582.
53. b) M. C. Lensen, K. Takazawa, J. A. A. Elemans, C. R. L. P. N. Jeukens, P. C. M. Christianen, J. C. Maan, A. E. Rowan, R. J. M. Nolte, Chem. Eur. J. 2004, 10, 831.
54. c) D. Monti, M. Venanzi, M. Russo, G. Bussetti, C. Goletti, M. Montalti, N. Zaccheroni, L. Prodi, R. Rella, M. G. Manera, G. Mancini, C. Di Natale, R. Paolesse, New J. Chem. 2004, 28, 1123.
55. a) T. Sato, Y. Sato, Y. Umeyama, A. Teramoto, Y. Nagamura, J. Wagner, D. Weng, Y. Okamoto, K. Hatada, M. M. Green, Macromolecules 1993, 26, 4551.
56. b) G. Gottarelli, G. P. Spada, Circular Dichroism, Principles and Applications, 2nd ed. (Eds: N. Berova, K. Nakanishi, R. W. Woody), Wiley, New York 2000, pp. 547-561.