Luminescent Liquid Crystals Derived from 9,10-Bis(Phenylethynyl)anthracene

Chemistry of Materials

Volumn 16, Issue 7, 2004, Pages 1377-1383

  Giménez, Raquel ^a   Piñol, Milagros ^a   Serrano, José Luis ^a  

^a CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENCE; LUMINESCENCE; PLASTIC FILMS;

NEMATIC COMPOUNDS;

LIQUID CRYSTALS;

9,10 BIS(PHENYLETHYNYL)ANTHRACENE; ANTHRACENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DEVICE; FILM; FLUORESCENCE; LIQUID CRYSTAL; LUMINESCENCE; MOLECULAR WEIGHT; SYNTHESIS;

EID: 1842679179     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm030582u     Document Type: Article

References (64)

1. Demus, D., Goodby, J., Gray, G. W., Spiess, H.-W., Vill, V., Eds.; Handbook of Liquid Crystals; Wiley-VCH: Weinheim, 1998; vol. 1, ch. IX, p 731.
2. Examples of rodlike intrinsically luminescent LC. (a) Subramanian, R.; Patterson, L. K.; Levanon, H. Chem. Phys. Lett. 1982, 93, 578.
3. (b) David, C.; Baeyens-Volant, D. Mol. Cryst. Liq. Cryst. 1984, 106, 45.
4. (c) Bubel, O. N.; Bezborodov, U. S.; Rachkevich, V. S. Zh. Org. Khim. 1982, 18, 1240.
5. (d) Ikeda, T.; Kuhihara, S.; Tazuke, S. J. Phys. Chem. 1990, 94, 6550.
6. (e) Chudgar, N. K.; Parekh, M. K., Madhavrao, S. S.; Sharma, H. C. Liq. Cryst. 1995, 19, 807.
7. (f) Gill, R. E.; Meetsma, A.; Hadziioannou, G. Adv. Mater. 1996, 8, 212.
8. (g) Davey, A. P.; Howard, R. G.; Blau, W. J. J. Mater. Chem. 1997, 7, 417.
9. (h) Strehmel, B.; Sarker, A. M.; Malpert, J. H.; Strehmel, V.; Seifert, H.; Neckers, D. C. J. Am. Chem. Soc. 1999, 121, 1226.
10. (i) Kim, S.; Park, S. Y. Mol. Cryst. Liq. Cryst., Sect. A 1999, 337, 405.
11. (j) Bacher, A.; Bentley, P. G.; Bradley, D. D. C.; Douglas, L. K.; Glarvey, P. A.; Grell, M.; Whitehead, K. S.; Turner, M. L. J. Mater. Chem. 1999, 9, 2985.
12. (k) Attias, A.-J.; Cavalli, C.; Bloch, B.; Guillou, N.; Noël, C. Chem. Mater. 1999, 11, 2057.
13. (l) Attias, A.-J.; Hapiot, P.; Wintgens, V.; Valat, P. Chem. Mater. 2000, 12, 461.
14. (m) Sumiyoshi, T.; Takahashi, I.; Tsuboi, Y.; Miyasaka, H.; Itaya, A.; Asahi, T.; Masuhara, H. Thin Solid Films 2000, 370, 285.
15. (n) Oriol, L.; Piñol, M.; Serrano, J. L.; Martínez, C.; Alcalá, R.; Cases, R.; Sánchez, C. Polymer 2001, 42, 2737
16. (o) Sentman, A. C.; Gin, D. L. Adv. Mater. 2001, 13 (18), 1398.
17. (p) Sato, N.; Ishii, R.; Nakashima, S.; Yonetake, K.; Kido, J. Liq. Cryst. 2001, 28, 1211.
18. (q) Schenning, A. P. H. J.; Kilbinger, A. F. M.; Biscarini, F.; Cavallini, M.; Cooper, H. J.; Derrick, P. J.; Feast, W. J.; Lazzaroni, R.; Leclere, Ph.; McDonell, L. A.; Meijer, E. W.; Meskers, S. C. J. J. Am. Chem. Soc. 2002, 124, 1269.
19. (r) Millaruelo, M.; Oriol, L.; Piñol, M.; Sáez, P. L.; Serrano, J. L. J. Photochem. Photobiol. A 2003,155, 29.
20. (s) Haristoy, D.; Tsiourvas, D. Chem. Mater. 2003, 15, 2079.
21. Examples of fluorescent phasmidic liquid crystals: (a) Hoag, B. P.; Gin, D. L. Adv. Mater. 1998, 10, 1546.
22. (b) Levitsky, I. A.; Kishikawa, K.; Eichhorn, S. M.; Swager, T. M. J. Am. Chem. Soc. 2000, 122, 2474.
23. Disklike: (a) Ecoffet, C.; Markovitsi, D.; Jallabert, C.; Strzelecka, H. ; Veber, M. Thin Solid Films 1994, 242, 83.
24. (b) Marguet, S.; Markovitsi, D.; Goldmann, D.; Janietz, D.; Praefcke, K. ; Singer, D. J. Chem. Soc., Faraday Trans. 1997, 93, 147.
25. (c) Cormier, R. A.; Gregg, B. A. Chem. Mater. 1998, 10, 1309.
26. (d) Rohr, U.; Schlichting, P.; Böhm, A.; Gross, M.; Meerholz, K.; Bräuchle, C.; Müllen, K. Angew. Chem., Int. Ed. 1998, 37, 1434.
27. (e) Ito, S.; Herwig, P. T.; Böhme, T.; Rabe, J. P.; Rettig, W.; Müllen, K. J. Am. Chem. Soc. 2000, 122, 7698.
28. (f) Benning, S.; Kitzerow, H.-S.; Bock, H.; Achard, M.-F. Liq. Cryst. 2000, 27, 901.
29. (g) Benning, S. A.; Hassheider, T.; Keuker-Bauman, S.; Bock, H.; Salla, F. D.; Frauenheim, T.; Kitzerow, H.-S. Liq. Cryst. 2001, 28, 1105.
30. (h) Attias, A.-J.; Cavalli, C.; Donnio, B.; Guillon, D.; Hapiot, P.; Malthête, J. Chem. Mater. 2002, 14, 375.
31. (a) Adam, D.; Schuhmacher, P.; Simmerer, J.; Häussling, L.; Siemensmeyer, K.; Etzbach, K. H.; Ringsdorf, H.; Haarer, D. Nature 1994, 371, 141.
32. (b) For a review see Lüssem, G.; Wendorff, J. H. Polym. Adv. Technol. 1998, 9, 443.
33. (a) Grell, M.; Bradley, D. D. C. Adv. Mater. 1999, 11, 895 and refs therein.
34. (b) Eglin, M.; Montali, A.; Palmans, A. R. A.; Tervoort, T.; Smith, P.; Weder, Ch. J. Mater. Chem. 1999, 9, 2221.
35. (c) Palmans, A. R. A.; Eglin, M.; Montali, A.; Weder, C.; Smith, P. Chem. Mater. 2000, 12, 472.
36. (a) Furst, M.; Kallman, H.; Brown, F. H. J. Chem. Phys. 1957, 26, 1321.
37. (b) Zweig, A.; Maurer, A. H.; Roberts, B. G. J. Org. Chem. 1967, 32, 1322.
38. (c) Maulding, D. R.; Roberts, B. G. J. Org. Chem. 1969, 34, 1734.
39. (d) Heller, C. A.; Henry, R. A.; McLaughlin, B. A.; Bliss, D. E. J. Chem. Eng. Data 1974, 19, 214.
40. (a) Maulding, D. R.; Zweig, A. U.S. Patent 3729426, 1973.
41. (b) Gill, S. K. Aldrichimica Acta 1983, 16, 59.
42. (c) Hanhela, P. J.; Paul, D. B. Aust. J. Chem. 1984, 37, 553.
43. (d) Nakatsuji, S.; Matsuda, K.; Uesugi, Y.; Nakashima, K.; Akiyama, S.; Fabian, W. J. Chem. Soc., Perkin Trans. 1 1992, 755.
44. (e) Li, B.; Miao, W.; Cheng, L. Dyes Pigm. 2000, 46, 81.
45. See for example: Cicerone, M. T.; Blackburn, F. R.; Ediger, M. D. J. Chem. Phys. 1995, 102, 47.
46. Ishibashi, T. Eur. Pat. Appl. EP 1072668 A2 31, 2001.
47. (a) Swager, T. M.; Gil, D. J.; Wrighton, M. S. J. Phys. Chem. 1995, 99, 4886.
48. (b) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
49. Levitus, M.; Garcia-Garibay, M. A. J. Phys. Chem. A 2000, 104, 8632.
50. Shinohara, K.-I.; Kato, F.; Minami, H.; Higuchi, H. Polymer 2001, 42, 8483.
51. (a) Sonogashira, K.; Toda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
52. (b) Takahashi, S.; Yuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
53. Nguyen, P.; Todd, S.; van den Biggelaar, D.; Taylor, N. J.; Marder, T. B.; Wittmann, F.; Friend, R. H. Synlett 1994, 299.
54. (a) Malthête, J.; Leclercq, M.; Dvolaitzky, M.; Gabard, J.; Billard, J.; Pontikis, V.; Jacques, J. Mol. Cryst. Liq. Cryst. 1973, 1973, 233.
55. (b) Pugh, C.; Percec, V. Polym. Bull. 1990, 23, 177.
56. (c) Viney, C.; Twieg, R. J.; Dannels, C. M.; Chang, M. Y. Mol. Cryst. Liq. Cryst. Lett. 1990, 7, 147.
57. (d) Nguyen, P.; Lesley, G.; Dai, C.; Taylor, N. J.; Marder, T. B.; Chu, V.; Viney, C.; Ledoux, I.; Zyss, J. In Applications of Organometallic Chemistry in the Preparation and Processing of Advanced Materials; Harrod, J. F., Laine, R. M., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1995; p 333.
58. Tanaka, M.; Hayashi, H.; Matsumoto, S.; Casino, S.; Mogi, K. Bull. Soc. Chem. Jpn. 1997, 70, 329.
59. (a) Aihara, J.; Kushibi, G.; Matsunaga, Y. Bull. Soc. Chem. Jpn. 1973, 46, 3584.
60. (b) Desiraju, G. R.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1977, 99, 4.
61. (a) Stevens, B.; Ban; M. I. Trans. Faraday Soc. 1964, 60, 1515.
62. (b) Jenekhe, S. A.; Osaheni, J. A. Science 1994, 265, 765.
63. Rosenhauer, R.; Fischer, Th.; Stumpe, J.; Giménez, R.; Piñol, M.; Serrano, J. L.; Broer, D. Proc. SPIE 2002, 4799, 121.
64. The degree of order of the films (S) has been calculated from the measured absorbance perpendicular (A) and parallel (A′) to the electric field vector of the incident light by the following equation: S = (A - A′)/(A + 2A′).