Combination of an aromatic core and aromatic side chains which constitutes discotic liquid crystal and organogel supramolecular assemblies

Langmuir

Volumn 21, Issue 4, 2005, Pages 1261-1268

  Ishi I, Tsutomu ^a   Hirayama, Tomoyuki ^b   Murakami, Ko Ichi ^a   Tashiro, Hiroshi ^a   Thiemann, Thies ^a   Kubo, Kanji ^a   Mori, Akira ^a   Yamasaki, Sumio ^b   Akao, Tetsuyuki ^c   Tsuboyama, Akira ^d   Mukaide, Taihei ^d   Ueno, Kazunori ^d   Mataka, Shuntaro ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b KYUSHU SANGYO UNIVERSITY   (Japan)

^c FUKUOKA INDUSTRIAL TECHNOLOGY CENTER   (Japan)

^d CANON INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CONDENSATION; CRYSTALLINE MATERIALS; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; GELS; LIGHT EMITTING DIODES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL MICROSCOPY; SCANNING ELECTRON MICROSCOPY; SUPRAMOLECULAR CHEMISTRY; X RAY DIFFRACTION ANALYSIS;

AROMATIC CORE; COLUMNAR LIQUID CRYSTALS; DISCOTIC LIQUID CRYSTALS; ORGANOGEL SUPRAMOLECULAR ASSEMBLIES;

LIQUID CRYSTALS;

EID: 14044273502     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la047874+     Document Type: Article

References (60)

1. For reviews of discotic liquid crystals see: (a) Chandrasekhar, S. In Handbook of Liquid Crystals; Demus, D., Goodby, J., Gray, G. W., Spiess, H.-W., Vill, V., Eds.; WILEY-VCH: Weinheim, 1998; Vol. 2B, Chapter 8. (b) Guillon, D. Struct. Bonding 1999, 95, 41-82.
2. For reviews of discotic liquid crystals see: (a) Chandrasekhar, S. In Handbook of Liquid Crystals; Demus, D., Goodby, J., Gray, G. W., Spiess, H.-W., Vill, V., Eds.; WILEY-VCH: Weinheim, 1998; Vol. 2B, Chapter 8. (b) Guillon, D. Struct. Bonding 1999, 95, 41-82.
3. Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097.
4. For reviews of organogels see: (a) Tereth, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3159. (b) Esch, J. V.; Schoonbeek, F.; de Loose, M.; Veen, E. M.; Kellogg, R. M.; Feringa, B. L. Supramol. Sci. 1999, 6, 233-259. Shinkai, S.; Murata, K. J. Mater. Chem. 1998, 8, 485-495. Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237-1247. (e) Gronwald, O.; Shinkai, S. Chem. Eur. J. 2002, 7, 4328-4334.
5. For reviews of organogels see: (a) Tereth, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3159. (b) Esch, J. V.; Schoonbeek, F.; de Loose, M.; Veen, E. M.; Kellogg, R. M.; Feringa, B. L. Supramol. Sci. 1999, 6, 233-259. Shinkai, S.; Murata, K. J. Mater. Chem. 1998, 8, 485-495. Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237-1247. (e) Gronwald, O.; Shinkai, S. Chem. Eur. J. 2002, 7, 4328-4334.
6. For reviews of organogels see: (a) Tereth, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3159. (b) Esch, J. V.; Schoonbeek, F.; de Loose, M.; Veen, E. M.; Kellogg, R. M.; Feringa, B. L. Supramol. Sci. 1999, 6, 233-259. Shinkai, S.; Murata, K. J. Mater. Chem. 1998, 8, 485-495. Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237-1247. (e) Gronwald, O.; Shinkai, S. Chem. Eur. J. 2002, 7, 4328-4334.
7. For reviews of organogels see: (a) Tereth, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3159. (b) Esch, J. V.; Schoonbeek, F.; de Loose, M.; Veen, E. M.; Kellogg, R. M.; Feringa, B. L. Supramol. Sci. 1999, 6, 233-259. Shinkai, S.; Murata, K. J. Mater. Chem. 1998, 8, 485-495. Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237-1247. (e) Gronwald, O.; Shinkai, S. Chem. Eur. J. 2002, 7, 4328-4334.
8. For reviews of organogels see: (a) Tereth, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3159. (b) Esch, J. V.; Schoonbeek, F.; de Loose, M.; Veen, E. M.; Kellogg, R. M.; Feringa, B. L. Supramol. Sci. 1999, 6, 233-259. Shinkai, S.; Murata, K. J. Mater. Chem. 1998, 8, 485-495. Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237-1247. (e) Gronwald, O.; Shinkai, S. Chem. Eur. J. 2002, 7, 4328-4334.
9. (a) Christ, T.; Glüsen, B.; Greiner, A.; Kettner, A.; Sander, R.; Stümpften, V.; Tsukruk, V.; Wendorff, J. H. Adv. Mater. 1997, 9, 48-51.
10. (b) Hassheider, T.; Benning, S. A.; Kitzerow, H.-S.; Achard, M.-F.; Bock, H. Angew. Chem., Int. Ed. 2001, 39, 2060-2063.
11. van de Craats, A. M.; Stutzmann, N.; Bunk, O.; Nielsen, M. M.; Watson, M.; Müllen, K.; Chanzy, H. D.; Sirringhaus, H.; Friend, R. H. Adv. Mater. 2003, 15, 495-499.
12. (a) Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Science 2001, 293, 1119-1122.
13. (b) Ajayaghosh, A.; George, S. J.; Praveen, V. K. Angew. Chem., Int. Ed. 2003, 42, 332-335.
14. (a)Watson, M.D.; Fechtenkötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267-1300 and references therein,
15. (b) Watson, M. D.; Debije, M. G.; Warman, J. M.; Müllen, K. J. Am. Chem. Soc. 2004, 126, 766-771.
16. (c) Terasawa, N.; Monobe, H.; Kiyohara, K.; Shimizu, Y. Chem. Commun. 2003, 1678-1679.
17. (d) Kimura, M.; Saito, Y.; Ohta, K.; Hanabusa, K.; Shirai, H. Kobayashi, N. J. Am. Chem. Soc. 2002, 124, 5274-5275.
18. (e) Boden, N.; Bushby, R. J.; Headdock, G.; Lozman, O. R.; Wood, A. Liq. Cryst. 2001, 28, 139-144.
19. (f) Yatabe, T.; Harbison, M. A.; Brand, J. D.; Wagner, M.; Müllen, K.; Samori, P.; Rabe, J. P. J. Mater. Chem. 2000, 10, 1519-1525.
20. (g) Mohr, B.; Wegner, G.; Ohta, K. J. Chem. Soc. Chem. Commun. 1995, 995-996.
21. (h) Shimizu, Y.; Miya, M.; Miya, A.; Nagata, A.; Ohta, K.; Yamamoto, I.; Kusabayashi, S. Liq. Cryst. 1993, 14, 795-805.
22. (a) Ikeda, M.; Takeuchi, M.; Shinkai, S. Chem. Commun. 2003, 1354-1355.
23. (b) Shirakawa, M.; Kawano, S.; Fujita, N.; Sada, K.; Shinkai, S. J. Org. Chem. 2003, 68, 5037-5044.
24. (c) Tamaru, S.; Uchino, S.; Takeuchi, M.; Ikeda, M.; Hatano, T.; Shinkai, S. Tetrahedron Lett. 2002, 43, 3751-3735.
25. (d) Ajayaghosh, A.; George, S. J. J. Am. Chem. Soc. 2001, 123, 5148-5149.
26. (e) Engelkamp, H.; Middelbeek, S.; Nolte, R. J. M. Science 1999, 284, 785-788.
27. (f) van Nostrun, C. F.; Picken, S. J.; Schouten, A.-J.; Nolte, R. J. M. J. Am. Chem. Soc. 1995, 117, 9957-9965.
28. Barberá, J.; Rakitin, O. A.; Ros, M. B.; Torroba, T. Angew. Chem., Int. Ed. 1998, 37, 296-299 and references therein.
29. (a) Praefcke, K.; Singer, D.; Gündogan, B.; Gutbier, K.; Langer, M. Ber. Bunsen-Ges. Phys. Chem. 1993, 97, 1358-1361.
30. (b) Praefcke, K.; Singer, D.; Langer, M.; Kohne, B. Mol. Cryst. Liq. Cryst. 1992, 215, 121-126.
31. Hexaazatriphenylene-based discotic molecules with long alkyl chains: (a) Gearba, R. I.; Lehmann, M.; Levin, J.; Ivanov, D. A.; Koch, M. H. J.; Barberà, J.; Debije, M. G.; Piris, J.; Geerts, Y. H. Adv. Mater. 2003, 15, 1614-1618. (b) Ong, C. W.; Liao, S.-C.; Chang, T. H.; Hsu, H.-F. Tetrahedron Lett. 2003, 44, 1477-1480. Pieterse, K.; van Hal, P. A.; Kleppinger, R.; Vekemans, J. A. J. M.; Janssen, R. A. J.; Meijer, E. W. Chem. Mater. 2001, 13, 2675-2679. Kestemont, G.; de Halleux, V.; Lehmann, M.; Ivanov. D. A.; Watson, M.; Geerts, Y. H. Chem. Commun. 2001, 2074-2075. (e) Arikainen, E. O.; Boden, N.; Bushby, R. J.; Lozman, O. R.; Vinter, J. G.; Wood, A. Angew. Chem., Int. Ed. 2000, 39, 2333-2336.
32. Hexaazatriphenylene-based discotic molecules with long alkyl chains: (a) Gearba, R. I.; Lehmann, M.; Levin, J.; Ivanov, D. A.; Koch, M. H. J.; Barberà, J.; Debije, M. G.; Piris, J.; Geerts, Y. H. Adv. Mater. 2003, 15, 1614-1618. (b) Ong, C. W.; Liao, S.-C.; Chang, T. H.; Hsu, H.-F. Tetrahedron Lett. 2003, 44, 1477-1480. Pieterse, K.; van Hal, P. A.; Kleppinger, R.; Vekemans, J. A. J. M.; Janssen, R. A. J.; Meijer, E. W. Chem. Mater. 2001, 13, 2675-2679. Kestemont, G.; de Halleux, V.; Lehmann, M.; Ivanov. D. A.; Watson, M.; Geerts, Y. H. Chem. Commun. 2001, 2074-2075. (e) Arikainen, E. O.; Boden, N.; Bushby, R. J.; Lozman, O. R.; Vinter, J. G.; Wood, A. Angew. Chem., Int. Ed. 2000, 39, 2333-2336.
33. Hexaazatriphenylene-based discotic molecules with long alkyl chains: (a) Gearba, R. I.; Lehmann, M.; Levin, J.; Ivanov, D. A.; Koch, M. H. J.; Barberà, J.; Debije, M. G.; Piris, J.; Geerts, Y. H. Adv. Mater. 2003, 15, 1614-1618. (b) Ong, C. W.; Liao, S.-C.; Chang, T. H.; Hsu, H.-F. Tetrahedron Lett. 2003, 44, 1477-1480. Pieterse, K.; van Hal, P. A.; Kleppinger, R.; Vekemans, J. A. J. M.; Janssen, R. A. J.; Meijer, E. W. Chem. Mater. 2001, 13, 2675-2679. Kestemont, G.; de Halleux, V.; Lehmann, M.; Ivanov. D. A.; Watson, M.; Geerts, Y. H. Chem. Commun. 2001, 2074-2075. (e) Arikainen, E. O.; Boden, N.; Bushby, R. J.; Lozman, O. R.; Vinter, J. G.; Wood, A. Angew. Chem., Int. Ed. 2000, 39, 2333-2336.
34. Hexaazatriphenylene-based discotic molecules with long alkyl chains: (a) Gearba, R. I.; Lehmann, M.; Levin, J.; Ivanov, D. A.; Koch, M. H. J.; Barberà, J.; Debije, M. G.; Piris, J.; Geerts, Y. H. Adv. Mater. 2003, 15, 1614-1618. (b) Ong, C. W.; Liao, S.-C.; Chang, T. H.; Hsu, H.-F. Tetrahedron Lett. 2003, 44, 1477-1480. Pieterse, K.; van Hal, P. A.; Kleppinger, R.; Vekemans, J. A. J. M.; Janssen, R. A. J.; Meijer, E. W. Chem. Mater. 2001, 13, 2675-2679. Kestemont, G.; de Halleux, V.; Lehmann, M.; Ivanov. D. A.; Watson, M.; Geerts, Y. H. Chem. Commun. 2001, 2074-2075. (e) Arikainen, E. O.; Boden, N.; Bushby, R. J.; Lozman, O. R.; Vinter, J. G.; Wood, A. Angew. Chem., Int. Ed. 2000, 39, 2333-2336.
35. Hexaazatriphenylene-based discotic molecules with long alkyl chains: (a) Gearba, R. I.; Lehmann, M.; Levin, J.; Ivanov, D. A.; Koch, M. H. J.; Barberà, J.; Debije, M. G.; Piris, J.; Geerts, Y. H. Adv. Mater. 2003, 15, 1614-1618. (b) Ong, C. W.; Liao, S.-C.; Chang, T. H.; Hsu, H.-F. Tetrahedron Lett. 2003, 44, 1477-1480. Pieterse, K.; van Hal, P. A.; Kleppinger, R.; Vekemans, J. A. J. M.; Janssen, R. A. J.; Meijer, E. W. Chem. Mater. 2001, 13, 2675-2679. Kestemont, G.; de Halleux, V.; Lehmann, M.; Ivanov. D. A.; Watson, M.; Geerts, Y. H. Chem. Commun. 2001, 2074-2075. (e) Arikainen, E. O.; Boden, N.; Bushby, R. J.; Lozman, O. R.; Vinter, J. G.; Wood, A. Angew. Chem., Int. Ed. 2000, 39, 2333-2336.
36. (a) Mataka, S.; Eguchi, H.; Takahashi, K.; Hatta, T.; Tashiro, M. Bull. Chem. Soc. Jpn. 1989, 62, 3127-3131.
37. (b) Mataka, S.; Shimojyo, Y.; Hashimoto, I.; Tashiro, M. Liebigs Ann. 1995, 1823-1825.
38. (c) Komin, A. P.; Carmack, M. J. Heterocycl. Chem. 1975, 12, 829-833.
39. (a) Destrade, C.; Foucher, P.; Gasparoux, H.; Tinh, N. H.; Levelut, A. M.; Malthete, J. Mol. Cryst. Liq. Cryst. 1984, 106, 121-146.
40. (b) Kumar, S.; Wachtel, E. J.; Keinan, E. J. Org. Chem. 1993, 58, 3821-3827.
41. (c) Serrette, A. G.; Lai, C. K.; Swager, T. M. Chem. Mater. 1994, 6, 2252-2268.
42. (d) Terasawa, N.; Monobe, H.; Kiyohara, K.; Shimizu, Y. Chem. Lett. 2003, 32, 214-215.
43. In the calculated structures by MM method, the intramolecular nonbonded N⋯N distances (1.14-1.18 nm for small space, 1.51-1.59 nm for large space) in 3a with the biphenylene spacer are longer than those (0.76-0.80 nm for small space, 1.09-1.12 nm for large space) in 3d with the phenylene spacer, suggesting the possible entanglement at the terminal moieties. A similar trend was observed in the comparison of 3c with 3e.
44. A weak and broad halo was observed in the wide angle region. A shoulder detected ca. 24°degree would be attributed to the intracolumnar disk-disk distance of ca. 0.37 nm, which is comparable to those (0.35-0.36 nm) of alkyl-chain-containing aryl-substituted triphenylenes and hexaazatriphenylenes: see ref 11e and Boden, N.; Bushby, R. J.; Headdock, G.; Lozman, O. R.; Wood, A. Liq. Cryst. 2001, 28, 139 -144. Around room temperature, 3a indicated weak and broad reflections, suggesting the formation of an amorphous type solid. In contrast, 3c showed the multiple reflections arising from the formation of a crystalline solid at the lower temperature.
45. (a) Hashimoto, M.; Ujiie, S.; Mori, A. Adv. Mater. 2003, 15, 797-800.
46. (b) Ito, S.; Herwig, P. T.; Böhme, T.; Rabe, J. P.; Rettig, W.; Müllen, K. J. Am. Chem. Soc. 2000, 122, 7698-7706.
47. XRD diffraction pattern of the xerogel of 3a was similar to that observed in the liquid crystalline state, although the reflections (100 reflection and halo) were detected very slightly. The result seems to suggest the formation of the hexagonal packing also in the organogel phase. Probably, almost organogel fibrous structure was decomposed during the freeze-drying treatment to prepare the xerogel.
48. c, respectively, along with further peak broadening (Figure S2-b). The results suggest the slow gelation process based on the formation of the π-stacked aggregate and the subsequent self-assembling and entanglement. The lower magnetic field shift during the gel generation process is not clear at the moment. We feel that the first higher magnetic field shift is ascribe to the π-π stacking among the HAT core moieties and the subsequent lower magnetic field shift to the further self-assembling and the entanglement of the formed π-stacked aggregate.
49. Ishi-i, T.; Iguchi, R.; Snip, E.; Ikeda, M.; Shinkai, S. Langmuir 2001, 17, 5825-5833.
50. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Book: Mill Valley, CA, 1983.
51. (a) Adam, D.; Schuhmacher, P.; Simmerer, J.; Häussling, L.; Siemensmeyer, K.; Etzbach, K. H.; Ringsdorf, H.; Haarer, D. Nature 1994, 372, 141-143.
52. (b) Wu, J.; Watson, M. D.; Müllen, K. Angew. Chem., Int. Ed. 2003, 42, 5329-5333.
53. van Gorp, J. J.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2002, 124, 14759-14769.
54. Palmans, A. R. A.; Vekemans, J. A. J. M.; Havinga, E. E.; Meijer, E. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 2648-2651.
55. Recently, it was reported that dimer of hexaazatriphenylene molecules is stabilized by complementary polytopic interactions between the hexaazatriphenylene cores, between the peripheral aromatic groups, and between the aromatic groups of one molecule and the hexaazatriphenylene core of another: Lozman, O. R.; Bushby, R. J.; Vinter, J. G. Perkin 2 2001, 1446-1452. In the present system, the complementary polytopic interactions around the extended central core including the hexaazatriphenylene ring and the biphenyl groups would play an important role to form the columnar-type aggregates whereas the terminal flexible groups of diarylamino and phenoxy groups maintain a subtle balance to stabilize the specific aggregation forms of discotic liquid crystals and organogels.
56. (a) Wong, K.-T.; Chien, Y.-Y.; Lian, Y.-L.; Lin, C.-C.; Chou, M.-Y.; Leung, M.-K. J. Org. Chem. 2002, 67, 1041-1044.
57. (b) Leung, M.-K.; Chou, M.-Y.; Su, Y. O.; Chiang, C. L.; Chen, H.-L.; Yang, C. F.; Yang, C.-C.; Lin, C.-C.; Chen, H.-T. Org. Lett. 2003, 5, 839-842.
58. Koene, B. E.; Loy, D. E.; Thompson, M. E. Chem. Mater. 1998, 10, 2235-2250.
59. Gampp, H.; Haspra, D.; Spieler, W.; Zuberbühler, A. D. Helv. Chim. Acta 1984, 67, 1019-1025.
60. Kohne, B.; Praefcke, K. Liebigs Ann. Chem. 1985, 522-528.