1,4-Bis(alkenyl)-2,5-dipiperidinobenzenes: Minimal fluorophores exhibiting highly efficient emission in the solid state

Angewandte Chemie - International Edition

Volumn 48, Issue 20, 2009, Pages 3653-3656

  Shimizu, Masaki ^a   Takeda, Youhei ^a   Higashi, Masahiro ^a   Hiyama, Tamejiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Arenes; Chromophores; Fluorescence; Luminescence; Materials science

Indexed keywords

ALKENYL; ALKENYL GROUPS; ARENES; AROMATIC COMPONENTS; BENZENE RING; EFFICIENT EMISSION; EMISSION COLOR; POLYSTYRENE THIN FILMS; UV LIGHT; VISIBLE LIGHT;

AROMATIC COMPOUNDS; BENZENE; CHROMOPHORES; LIGHT; LIGHT EMISSION; POLYSTYRENES; THIN FILMS;

FLUORESCENCE;

EID: 70349783706     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900963     Document Type: Article

References (78)

1. a) Highly Efficient OLEDs with Phosphorescent Materials (Ed.: H. Yersin), Wiley-VCH, Weinheim, 2008;
2. b) Organic Light-Emitting Devices. Synthesis Properties and Applications (Eds.: K. Mullen, U. Scherf), Wiley-VCH, Weinheim, 2006;
3. c) R. H. Friend, R. W Gymer, A. B. Holmes, J. H. Burroughes, R. N. Marks, C. Taliani, D. D. C. Bradley, D. A. Dos Santos, J. L. Bredas, M. Logdlund, W R. Salaneck, Nature 1999, 397, 121-128.
4. a) I. D. W Samuel, G. A. Turnbull, Chem. Rev. 2007, 107, 1272-1295;
5. b) I. D. W Samuel, G A. Turnbull, Mater. Today 2004, 7, 28-35;
6. c) U. Scherf, S. Riechel, U. Lemmer, R. F. Mahrt, Curr. Opin. Solid State Mater. Sci. 2001, 5, 143-154;
7. d) M. D. McGehee, A.J. Heeger, Adv. Mater. 2000, 12, 1655-1668;
8. e) G Kranzelbinder, G Leising, Rep. Prog. Phys. 2000, 63, 729-762;
9. f)N. Tessler, Adv. Mater. 1999, 11, 363-370;
10. g) V. G. Kozlov, S. R. Forrest, Curr. Opin. Solid State Mater. Sci. 1999, 4, 203-208.
11. Reviews on fluorescent sensors: a) S. W Thomas Iii, G D. Joly, T M. Swager, Chem. Rev. 2007, 107, 1339-1386;
12. b) L. Basabe-Desmonts, D. N. Reinhoudt, M. Crego-Calama, Chem. Soc. Rev. 2007, 36, 993-1017;
13. c) O. S. Wolfbeis, J. Mater. Chem. 2005, 15, 2657-2669;
14. d) J. F. Callan, A. P. de Silva, D. C. Magri, Tetrahedron 2005, 61, 8551-8588;
15. e) R. Martinez-Manez, F. Sancenon, Chem. Rev. 2003, 103, 4419-4476;
16. f) A. P. de Silva, H. Q. N. Gunaratne, T Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, T.E. Rice, Chem. Rev. 1997, 97, 1515-1566.
17. Selected examples of solid-state fluorescent sensors: g) S. Sreejith, K. P. Divya, A. Ajayaghosh, Chem. Commun. 2008, 2903 - 2905;
18. h) T J. Dale, J. Rebek, J. Am. Chem. Soc. 2006, 128, 4500-4501;
19. i) S. W Zhang, T M. Swager, J. Am. Chem. Soc. 2003, 125, 3420-3421;
20. j) J. S. Yang, T M. Swager, J. Am. Chem. Soc. 1998, 120, 11864-11873;
21. k) J. S. Yang, T M. Swager, J. Am. Chem. Soc. 1998, 120, 5321-5322.
22. a) T P. I. Saragi, T Spehr, A. Siebert, T Fuhrmann-Lieker, J. Salbeck, Chem. Rev. 2007, 107, 1011-1065;
23. b) P. L. Burn, S. C. Lo, I. D. W Samuel, Adv. Mater. 2007, 19, 1675-1688;
24. c) I. F. Perepichka, D. F. Perepichka, H. Meng, F. Wudl, Adv. Mater. 2005, 17, 2281 -2305;
25. d) L. Akcelrud, Prog. Polym. Sci. 2003, 28, 875-962;
26. e) U. Mitschke, P. Bauerle, J. Mater. Chem. 2000, 10, 1471-1507;
27. f) D. Y. Kim, H. N. Cho, C. Y. Kim, Prog. Polym. Sci. 2000, 25, 1089-1139;
28. g) A. Kraft, A. C. Grimsdale, A. B. Holmes, Angew. Chem. 1998, 110, 416-443;
29. Angew. Chem. Int. Ed. 1998,37,402-428.
30. a) W Y Lai, R. Xia, Q. Y He, P. A. Levermore, W Huang, D. D. C. Bradley, Adv. Mater. 2009, 21, 355-360;
31. b) M. Shimizu, K. Mochida, T. Hiyama, Angew. Chem. 2008, 120, 9906-9910;
32. Angew. Chem. Int. Ed. 2008, 47, 9760-9764;
33. c)J. Huang, X. Qiao, Y Xia, X. Zhu, D. Ma, Y Cao, J. Roncali, Adv. Mater. 2008,20, 4172-4175;
34. d) M. Y Lai, C. H. Chen, W S. Huang, J. T. Lin, T. H. Ke, L. Y Chen, M. H. Tsai, C. C. Wu, Angew. Chem. 2008, 120, 591-595;
35. Angew. Chem. Int. Ed. 2008, 47, 581-585;
36. e) E. Ishow, A. Brosseau, G Clavier, K. Nakatani, P. Tauc, C. Fiorini-Debuisschert, S. Neveu, O. Sandre, A. Leaustic, Chem. Mater. 2008, 20, 6597-6599;
37. f)Y.T. Lee, C. L. Chiang, C. T. Chen, Chem. Commun. 2008, 217-219;
38. g) C. Kitamura, C. Matsumoto, N. Kawatsuki, A. Yoneda, K. Asada, T Kobayashi, H. Naito, Bull. Chem. Soc. Jpn. 2008, 81, 754-756;
39. h) Z. Chen, J. Bouffard, S. E. Kooi, T M. Swager, Macromolecules 2008, 41, 6672-6676;
40. i) A. Wakamiya, K. Mori, S. Yamaguchi, Angew. Chem. 2007, 119, 4351-4354;
41. Angew. Chem. Int. Ed. 2007, 46, 4273-4276;
42. j) J. Luo, Y Zhou, Z. Q. Niu, Q. F. Zhou, Y Ma, J. Pei, J. Am. Chem. Soc. 2007, 129, 11314-11315;
43. k) Z. Xie, H. Wang, F. Li, W Xie, L. Liu, B. Yang, L. Ye, Y Ma, Cryst. Growth Des. 2007, 7,2512-2516;
44. l) Y Li, F. Li, H. Zhang, Z. Xie, W Xie, H. Xu, B. Li, F. Shen, L. Ye, M. Hanif, D. Ma, Y Ma, Chem. Commun. 2007, 231-233;
45. m) C. H. Zhao, A. Wakamiya, Y. Inukai, S. Yamaguchi, J. Am. Chem. Soc. 2006, 128, 15934-15935;
46. n) A. Hayer, V. de Halleux, A. Kohler, A. El-Garoughy, E. W. Meijer, J. Barbera, J. Tant, J. Levin, M. Lehmann, J. Gierschner, J. Cornil, Y. H. Geerts, J. Phys. Chem. B 2006, 110, 7653-7659;
47. o) Y. Kim, J. Bouffard, S. E. Kooi, T. M. Swager, J. Am. Chem. Soc. 2005, 127, 13726-13731;
48. p) S. H. Lee, B. B. Jang, Z. H. Kafafi, J. Am. Chem. Soc. 2005, 127, 9071-9078;
49. q) K. L. Chan, M. J. McKiernan, C. R. Towns, A. B. Holmes, J. Am. Chem. Soc. 2005, 127, 7662-7663;
50. r) G Yui, S. Yin, Y Liu, J. Chen, X. Xu, X. Sun, D. Ma, X. Zhan, Q. Peng, Z. Shuai, B. Tang, D. Zhu, W. Fang, Y Luo, J. Am. Chem. Soc. 2005, 127, 6335-6346;
51. s) T. C. Chao, Y.T. Lin, C. Y Yang, T. S. Hung, H. C. Chou, C. C. Wu, K. T. Wong, Adv. Mater. 2005, 17, 992-996;
52. t) K. T. Wong, Y Y Chien, R. T. Chen, C. F. Wang, Y T. Lin, H. H. Chiang, P. Y Hsieh, C. C. Wu, C. H. Chou, Y O. Su, G H. Lee, S. M. Peng, J. Am. Chem. Soc. 2002, 124, 11576-11577;
53. u) M. Ariu, D. G Lidzey, M. Sims, A. J. Cadby, P. A. Lane, D. D. C. Bradley, J. Phys. Condens. Matter 2002, 14, 9975 -9986.
54. Pyromellitic diimides were recently reported to act as minimal cores for n-channel transistor materials with high mobility. Q. Zheng, J. Huang, A. Sarjeant, H. E. Katz, J. Am. Chem. Soc. 2008,130,14410-14411.
55. Unpublished results. Details will be reported in due course.
56. Cyanovinyl-substituted dimethoxybenzenes were reported to exhibit fluorescence in ethanol with emission maxima ranging from 500 to 580 nm; a) K. Y Chu, J. Griffiths, D. Ward, J. Chem. Res. Synop. 1981,300 - 301;
57. b) K. Y Chu, J. Griffiths, D. Ward, J. Chem. Res. Miniprint 1981, 3701-3721.
58. Z. Xie, B. Yang, L. Liu, M. Li, D. Lin, Y Ma, G Cheng, S. Liu, / Phys. Org. Chem. 2005, 18, 962-973.
59. a) T. Kobayashi, T. Eda, O. Tamura, H. Ishibashi, J. Org. Chem. 2002, 67, 3156-3159;
60. b)J. P. Wolfe, S. L. Buchwald, J. Org. Chem. 2000, 65, 1144-1157. See the Supporting Information.
61. UV irradiation of 1-5 both in cyclohexane and in the crystal with a 400 W high-pressure mercury lamp at room temperature for 1 h resulted in no change of their absorption and fluorescence spectra.
62. CCDC 719745 (3) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc. cam.ac.uk/data-request/cif.
63. The molecular structure was optimized by DFT methods at the B3LYP/6-31G(d) level with the crystal structure as the initial geometry.
64. For the preparation of 1, 2, 4, and 5, see the Supporting Information. These benzenes are also soluble in organic solvents such as CH2Cl2, CHCl3, THF, and toluene.
65. Absorption and fluorescence spectra of 1-5 in cyclohexane and fluorescence spectra in thin neat films and in polystyrene films are shown in the Supporting Information.
66. a) C. T. Chen, Chem. Mater. 2004, 16, 4389-4400;
67. b) Y H. Song, S. J. Yeh, C. T. Chen, Y Chi, C. S. Liu, J. K. Yu, Y H. Hu, P. T. Chou, S. M. Peng, G H. Lee, Adv. Funct. Mater. 2004, 14, 1221 -1226;
68. c) C. L. Chiang, M. F. Wu, D. C. Dai, Y S. Wen, J. K. Wang, C. T. Chen, Adv. Funct. Mater. 2005, 15, 231 -238;
69. d) Y L. Tung, S. W Lee, Y Chi, Y T Tao, C. H. Chien, Y M. Cheng, P. T. Chou, S. M. Peng, C. S. Liu, J. Mater. Chem. 2005, 15, 460-464;
70. e) Ref. [5i];
71. f) Ref. [5f];
72. g) A. Wakamiya, N. Sugita, S. Yamaguchi, Chem. Lett. 2008,37, 1094-1095.
73. a) J. Luo, Z. Xie, J. W Y Lam, L. Cheng, H. Chen, C. Qiu, K. Hoi Sing, X. Zhan, Y Liu, D. Zhu, T. Ben Zhong, Chem. Commun. 2001,1740-1741;
74. b) K. Itami, Y Ohashi, J. I. Yoshida, J. Org. Chem. 2005, 70, 2778-2792;
75. c) H. Tong, Y Hong, Y. Dong, M. Haussler, J. W Y Lam, Z. Li, Z. Guo, Z. Guo, B. Z. Tang, Chem. Commun. 2006, 3705-3707;
76. d) S. Kim, Q. Zheng, G S. He, D. J. Bharali, H. E. Pudavar, A. Baev, P. N. Prasad, Adv. Funct. Mater. 2006, 16, 2317-2323;
77. e) Z. Ning, Z. Chen, Q. Zhang, Y Yan, S. Qian, Y Cao, H. Tian, Adv. Funct. Mater. 2007, 17, 3799 - 3807;
78. f) Y Dong, J. W Y Lam, A. Qin, J. Sun, J. Liu, Z. Li, J. Sun, H. H. Y Sung, I. D. Williams, H. S. Kwok, B. Z. Tang, Chem. Commun. 2007, 3255-3257. Fluorescence spectra of 3 measured in a mixture of CH3CN/H2O are shown in the Supporting Information.