The Effect of Cyano Substitution on the Fluorescence Behavior of 1,2-Bis(pyridylphenyl)ethene

Asian Journal of Organic Chemistry

Volumn 3, Issue 6, 2014, Pages 686-690

  Nishio, Suguru ^a   Higashiguchi, Kenji ^a,b   Matsuda, Kenji ^a  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

1,2 bis(pyridylphenyl)ethene; Aggregate induced enhanced emission; Dyes pigments; Fluorescence; Photochemistry

Indexed keywords

EID: 84901847920     PISSN: 21935807     EISSN: 21935807     Source Type: Journal    
DOI: 10.1002/ajoc.201402024     Document Type: Article

References (43)

1. S. Rochat, T. M. Swager, ACS Appl. Mater. Interfaces 2013, 5, 4488-4502
2. F. Würthner, T. E. Kaiser, C. R. Saha-Möller, Angew. Chem. Int. Ed. 2011, 50, 3376-3410
3. Angew. Chem. 2011, 123, 3436-3473
4. H. Kobayashi, M. Ogawa, R. Alford, P. L. Choyke, Y. Urano, Chem. Rev. 2010, 110, 2620-2640.
5. J. B. Birks, Photophysics of Aromatic Molecules, Wiley, London, 1970.
6. J. Gierschner, S. Y. Park, J. Mater. Chem. C 2013, 1, 5818-5832
7. J. Gierschner, L. Lüer, B. Milián-Medina, D. Oelkrug, H.-J. Egelhaaf, J. Phys. Chem. Lett. 2013, 4, 2686-2697
8. T. Hinoue, Y. Shigenoi, M. Sugino, Y. Mizobe, I. Hisaki, M. Miyata, N. Tohnai, Chem. Eur. J. 2012, 18, 4634-4643
9. M. Shimizu, T. Hiyama, Chem. Asian J. 2010, 5, 1516-1531.
10. S. Choi, J. Bouffard, Y. Kim, Chem. Sci. 2014, 5, 751-755
11. D. Tleugabulova, Z. Zhang, J. D. Brennan, J. Phys. Chem. B 2002, 106, 13133-13138.
12. Y. Hong, J. W. Y. Lam, B. Z. Tang, Chem. Soc. Rev. 2011, 40, 5361-5388
13. J. Luo, Z. Xie, J. W. Y. Lam, L. Cheng, H. Chen, C. Qiu, H. S. Kwok, X. Zhan, Y. Liu, D. Zhu, B. Z. Tang, Chem. Commun. 2001, 1740-1741
14. G. Yu, S. Yin, Y. Liu, J. Chen, X. Xu, X. Sun, D. Ma, X. Zhen, Q. Peng, Z. Shuai, B. Z. Tang, D. Zhu, W. Fang, Y. Luo, J. Am. Chem. Soc. 2005, 127, 6335-6346
15. K. Itami, Y. Ohashi, J.-i. Yoshida, J. Org. Chem. 2005, 70, 2778-2792
16. Y. Liu, X. Tao, F. Wang, J. Shi, J. Sun, W. Yu, Y. Ren, D. Zou, M. Jiang, J. Phys. Chem. C 2007, 111, 6544-6549
17. M. Wang, D. Zhang, G. Zhang, D. Zhu, Chem. Commun. 2008, 4469-4471
18. W. Z. Yuan, P. Lu, S. Chen, J. W. Y. Lam, Z. Wang, Y. Liu, H. S. Kwok, Y. Ma, B. Z. Tang, Adv. Mater. 2010, 22, 2159-2163
19. Y. Hong, L. Meng, S. Chen, C. W. T. Leung, L.-T. Da, M. Faisal, D.-A. Silva, J. Liu, J. W. Y. Lam, X. Huang, B. Z. Tang, J. Am. Chem. Soc. 2012, 134, 1680-1689.
20. D. Ding, K. Li, B. Liu, B. Z. Tang, Acc. Chem. Res. 2013, 46, 2441-2453
21. K. Mizusawa, Y. Takaoka, I. Hamachi, J. Am. Chem. Soc. 2012, 134, 13386-13395
22. K. Mizusawa, Y. Ishida, Y. Takaoka, M. Miyagawa, S. Tsukiji, I. Hamachi, J. Am. Chem. Soc. 2010, 132, 7291-7293.
23. B.-K. An, J. Gierschner, S. Y. Park, Acc. Chem. Res. 2012, 45, 544-554
24. B.-K. An, S.-K. Kwon, S.-D. Jung, S. Y. Park, J. Am. Chem. Soc. 2002, 124, 14410-14415
25. B.-K. An, D.-S. Lee, J.-S. Lee, Y.-S. Park, H.-S. Song, S. Y. Park, J. Am. Chem. Soc. 2004, 126, 10232-10233
26. S.-J. Lim, B.-K. An, S. D. Jung, M.-A. Chung, S. Y. Park, Angew. Chem. Int. Ed. 2004, 43, 6346-6350
27. Angew. Chem. 2004, 116, 6506-6510
28. J. W. Chung, B.-K. An, S. Y. Park, Chem. Mater. 2008, 20, 6750-6755
29. J. W. Chung, Y. You, H. S. Huh, B.-K. An, S.-J. Yoon, S. H. Kim, S. W. Lee, S. Y. Park, J. Am. Chem. Soc. 2009, 131, 8163-8172
30. S. Kim, S.-J. Yoon, S. Y. Park, J. Am. Chem. Soc. 2012, 134, 12091-12097
31. J. W. Chung, S.-J. Yoon, B.-K. An, S. Y. Park, J. Phys. Chem. C 2013, 117, 11285-11291.
32. D. Oelkrug, A. Tompert, J. Gierschner, H.-J. Egelhaaf, M. Hanack, M. Hohloch, E. Steinhuber, J. Phys. Chem. B 1998, 102, 1902-1907
33. K.-H. Schweikart, M. Hohloch, E. Steinhuber, M. Hanack, L. Lüer, J. Gierschner, H.-J. Egelhaaf, D. Oelkrug, Synth. Met. 2001, 121, 1641-1642.
34. M. Piacenza, F. DellaSala, G. M. Farinola, C. Martinelli, G. Gigli, J. Phys. Chem. B 2008, 112, 2996-3004.
35. This microstalline state will be referred to as the solid state.
36. DFT calculations were performed by using the Gaussian09 package. See the Supporting Information for details.
37. 2=0.2040. CCDC 978716 contains the supplementary crystallographic data. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
38. P. A. Wood, S. J. Borwick, D. J. Watkin, W. D. S. Motherwell, F. H. Allen, Acta Crystallogr. Sect. B 2008, 64, 393-396;
39. S. Lee, A. B. Mallik, D. C. Fredrickson, Cryst. Growth Des. 2004, 4, 279-290.
40. G. R. Desiraju, T. Steiner, The Weak Hydrogen bond: In Structural Chemistry and Biology, Oxford University Press, Oxford, 1999.
41. F. C. Spano, Acc. Chem. Res. 2010, 43, 429-439
42. J. Gierschner, M. Ehni, H.-J. Egelhaaf, B. M. Medina, D. Beljonne, H. Benmansour, G. C. Bazan, J. Chem. Phys. 2005, 123, 144914.
43. We have discussed the difference in the emission rate constants of a cyanobis(biphenyl)ethene derivative between those in the aggregated state in water and in the solid state, see: T. Hirose, K. Higashiguchi, K. Matsuda, Chem. Asian J. 2011, 6, 1057-1063.