Mesomorphic organization and thermochromic luminescence of dicyanodistyrylbenzene-based phasmidic molecular disks: Uniaxially aligned hexagonal columnar liquid crystals at room temperature with enhanced fluorescence emission and semiconductivity

Advanced Functional Materials

Volumn 22, Issue 1, 2012, Pages 61-69

  Yoon, Seong Jun ^a   Kim, Jong H ^a   Kim, Kil Suk ^c   Chung, Jong Won ^a   Heinrich, Benoît ^b   Mathevet, Fabrice ^d   Kim, Pyosang ^c   Donnio, Bertrand ^b   Attias, André Jean ^d   Kim, Dongho ^c   Park, Soo Young ^a  

^a Seoul National University   (South Korea)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c Yonsei University   (South Korea)

^d SORBONNE UNIVERSITÉ   (France)

Author keywords

electro optical materials; liquid crystals; structure property relationships

Indexed keywords

COLUMNAR LIQUID CRYSTALS; CRYSTALLINE PHASIS; CRYSTALLINE STATE; CYANO GROUPS; DIPOLE COUPLING; ELECTRICAL CONDUCTIVITY; EMISSION COLOR; ENHANCED EMISSION; ENHANCED FLUORESCENCE EMISSION; FLUORESCENCE EMISSION; INTERMOLECULAR INTERACTIONS; ISOTROPIC MELT; MESOMORPHIC ORGANIZATION; MICRO WIRE; MICROMOLDING IN CAPILLARIES; MOLECULAR DISK; MOLECULAR MOTIONS; MULTI DOMAINS; PHOTOPHYSICAL PROPERTIES; PLANARIZATION; ROOM TEMPERATURE; SECONDARY BONDING; SELF-ASSEMBLE; SEMICONDUCTIVITY; SHEAR ALIGNMENT; STRUCTURE PROPERTY RELATIONSHIPS; TEMPERATURE DEPENDENT; THERMO-CHROMIC; THERMOCHROMISM; TIME-RESOLVED PL MEASUREMENT; TWO-COLOR;

COLOR; CRYSTALS; ELECTRIC CONDUCTIVITY; ELECTROOPTICAL MATERIALS; EXCITED STATES; LIQUID CRYSTALS; MOLECULES;

FLUORESCENCE;

EID: 84855319446     PISSN: 1616301X     EISSN: 16163028     Source Type: Journal    
DOI: 10.1002/adfm.201101818     Document Type: Article

References (55)

1. a) E. Kim, S. B. Park, Chem. Asian. J. 2009, 4, 1646
2. b) P. M. Beaujuge, C. M. AMB, J. R. Reynolds, Acc. Chem. Res. 2010, 43, 1396.
3. a) R. Davis, N. P. Rath, S. Das, Chem. Commun. 2004, 74
4. b) T. Mutai, H. Satou, K. Araki, Nat. Mater. 2005, 4, 685
5. c) H. Zhang, Z. Zhang, K. Ye, J. Zhang, Y. Wang, Adv. Mater. 2006, 18, 2369
6. d) T. Mutai, H. Tomoda, T. Ohkawa, Y. Yabe, K. Araki, Angew. Chem. Int. Ed. 2008, 47, 9522
7. e) Y. Zhao, H. Gao, Y. Fan, T. Zhou, Z. Su, Y. Liu, Y. Wang, Adv. Mater. 2009, 21, 3165
8. f) S. S. Babu, K. K. Kartha, A. Ajayaghosh, J. Phys. Chem. Lett. 2010, 1, 3413
9. g) S. Varghese, S. Das, J. Phys. Chem. Lett. 2011, 2, 863.
10. a) M. D. Curtis, J. Cao, J. W. Kampf, J. Am. Chem. Soc. 2004, 126, 4318
11. b) H. Moon, R. Zeis, E. J. Borkent, C. Besnard, A. J. Lovinger, T. Siegrist, C. Kloc, Z. Bao, J. Am. Chem. Soc. 2004, 126, 15322
12. c) R. Li, W. Hu, Y. Liu, D. Zhu, Acc. Chem. Res. 2010, 43, 529.
13. a) F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491
14. b) B. Moulton, M. J. Zaworotko, Chem. Rev. 2001, 101, 1629
15. c) X. Zhang, X. Zhang, K. Zou, C. S. Lee, S. T. Lee, J. Am. Chem. Soc. 2007, 129, 3527.
16. S. J. Yoon, J. W. Chung, J. Gierschner, K. S. Kim, M. G. Choi, D. Kim, S. Y. Park, J. Am. Chem. Soc. 2010, 132, 13675.
17. S. J. Yoon, S. Y. Park, J. Mater. Chem. 2011, 21, 8338.
18. a) F. Camerel, L. Bonardi, G. Ulrich, L. Charbonniére, B. Donnio, C. Bourgogne, D. Guillon, P. Retailleau, R. Ziessel, Chem. Mater. 2006, 18, 5009
19. b) F. Camerel, L. Bonardi, M. Schmutz, R. Ziessel, J. Am. Chem. Soc. 2006, 128, 4548
20. c) F. Camerel, J. Barberá, J. Otsuki, T. Tokimoto, Y. Shimazaki, L. Y. Chen, S. H. Liu, M. S. Lin, C. C. Wu, R. Ziessel, Adv. Mater. 2008, 20, 3462
21. d) C. Z. Li, Y. Matsuo, E. Nakamura, J. Am. Chem. Soc. 2009, 131, 17058
22. e) S. Frein, F. Camerel, R. Ziessel, J. Barberá, R. Deschenaux, Chem. Mater. 2009, 21, 3950
23. f) D. Pucci, A. Bellusci, A. Crispini, M. Ghedini, N. Godbert, E. I. Szerb, A. M. Talarico, J. Mater. Chem. 2009, 19, 7643.
24. a) Y. Sagara, T. Kato, Angew. Chem. Int. Ed. 2008, 47, 5175
25. b) V. N. Kozhevnikov, B. Donnio, D. W. Bruce, Angew. Chem. Int. Ed. 2008, 47, 6286
26. c) Y. Sagara, S. Yamane, T. Mutai, K. Araki, T. Kato, Adv. Funct. Mater. 2009, 19, 1869
27. d) S. Yamane, Y. Sagara, T. Kato, Chem. Commun. 2009, 3597.
28. a) C. D. Simpson, J. Wu, M. D. Watson, K. Müllen, J. Mater. Chem. 2004, 14, 494
29. b) S. Sergeyev, W. Pisula, Y. H. Geerts, Chem. Soc. Rev. 2007, 36, 1902
30. c) B. R. Kaafarani, Chem. Mater. 2011, 23, 378.
31. a) M. Yoshio, T. Mukai, H. Ohno, T. Kato, J. Am. Chem. Soc. 2004, 126, 994
32. b) T. Sakurai, K. Shi, H. Sato, K. Tashiro, A. Osuka, A. Saeki, S. Seki, S. Tagawa, S. Sasaki, H. Masunaga, K. Osaka, M. Takata, T. Aida, J. Am. Chem. Soc. 2008, 130, 13812
33. c) T. Yasuda, H. Ooi, J. Morita, Y. Akama, K. Minoura, M. Funahashi, T. Shimomura, T. Kato, Adv. Funct. Mater. 2009, 19, 411
34. d) Z. An, J. Yu, B. Domercq, S. C. Jones, S. Barlow, B. Kippelen, S. R. Marder, J. Mater. Chem. 2009, 19, 6688.
35. H. T. Nguyen, C. Destrade, J. Malthete, Adv. Mater. 1997, 9, 375.
36. a) B. P. Hoag, D. L. Gin, Adv. Mater. 1998, 10, 1546
37. b) K. E. Rowe, D. W. Bruce, J. Mater. Chem. 1998, 8, 331
38. c) F. Lincker, P. Bourgun, P. Masson, P. Didier, L. Guidoni, J. Y. Bigot, J. F. Nicoud, B. Donnio, D. Guillon, Org. Lett. 2005, 7, 1505
39. d) T. Yasuda, K. Kishimoto, T. Kato, Chem. Commun. 2006, 3399
40. e) J. Seo, S. Kim, S. H. Gihm, C. R. Park, S. Y. Park, J. Mater. Chem. 2007, 17, 5052
41. f) X. Li, A. Liu, S. Xun, W. Qiao, X. Wan, Z. Y. Wang, Org. Lett. 2008, 10, 3785
42. g) K. Isoda, T. Yasuda, T. Kato, J. Mater. Chem. 2008, 18, 4522
43. h) H. H. G. Tsai, L. C. Chou, S. C. Lin, H. S. Sheu, C. K. Lai, Tetrahedron Lett. 2009, 50, 1906
44. i) P. Zhang, B. Bai, H. Wang, S. Qu, Z. Yu, X. Ran, M. Li, Liq. Cryst. 2009, 36, 7
45. j) S. Zhang, Y. Guo, L. Wang, Q. Li, K. Zheng, X. Zhan, Y. Liu, R. Liu, L. J. Wan, J. Phys. Chem. C 2009, 113, 16232.
46. Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT, 2009.
47. A. Pérez, J. L. Serrano, T. Sierra, A. Ballesteros, D. de Saá, J. Barluenga, J. Am. Chem. Soc. 2011, 133, 8110.
48. B. Donnio, B. Heinrich, Th. Gulik-Grzywicki, H. Delacroix, D. Guillon, Chem. Mater. 1997, 9, 2951.
49. a) R. O. Loutfy, B. A. Arnold, J. Phys. Chem. 1982, 86, 4205
50. b) C. E. Kung, J. K. Reed, Biochemistry 1986, 25, 6114
51. c) S. Kim, J. Seo, S. Y. Park, J. Photochem. Photobiol. A: Chem. 2007, 191, 19.
52. T. Förster, K. Kasper, Z. Elektrochem. 1955, 59, 976.
53. E. Kim, Y. Xia, G. M. Whitesides, Nature 1995, 376, 581.
54. B. K. Kuila, A. K. Nandi, Macromolecules 2004, 37, 8577.
55. J. C. de Mello, H. F. Wittmann, R. H. Friend, Adv. Mater. 1997, 9, 230.