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New Journal of Chemistry
Page 6 of 7
DOI: 10.1039/C8NJ00455B
ARTICLE
Journal Name
15. T. Mutai, H. Tomoda, T. Ohkawa, Y. Yabe, K. Araki, Angew.
Chem. Int. Ed., 2008, 47, 9522.
16. Y. Shigemitsu, T. Mutai, H. Houjou, K. Araki, J. Phys. Chem. A,
2012, 116, 12041.
intramolecular hydrogen bonding is preferable for ESIPT, the
careful molecular design is required for obtaining an efficient
ESIPT. We herein investigated the synthesis and optical
characterizations of three 2-hydroxyphenylbenzimidazole
isomers having the methoxy group at various positions. In the
solution state, the double intramolecular hydrogen bonding
was quite effective to realize the robust ESIPT emission. The
ratio of LE/ESIPT emissions was influenced by the position of
methoxy group. These facts were carefully discussed based on
the DFT calculation. In the solid state, the different crystal
17. K. Skonieczny, A. I. Ciuciu, E. M. Nichols, V. Hugues, M.
,
Blanchard-Desce, L. Flamigni D. T. Gryko, J. Mater. Chem.,
2012, 22, 20649.
18. A. I. Ciuciu, L. Flamigni, K. Skonieczny, D. T. Gryko, Phys. Chem.
Chem. Phys., 2013, 15, 16907.
19. S. Kim, J. Seo, S. Y. Park, J. Photochem. Photobiol. A: Chem.,
2007, 191, 19.
packing structure such as the columnar π-π stacking and one
20. H.-H. G. Tsai, H.-L. S. Sun, C.-J. Tan, J. Phys. Chem. A, 2010,
114, 4065.
21. K.-Y. Chen, C.-C. Hsieh, Y.-M. Cheng, C.-H. Lai, P.-T. Chou,
Chem. Commun., 2006, 4395.
dimensional hydrogen bonding network resulted in the non-
fluorescent and fluorescent behavior, respectively. We believe
that the present findings shed light on the design of ESIPT-
22. J. Piechowska, D. T. Gryko, J. Org. Chem., 2011, 76, 10220.
23. H.-W. Tseng, T.-C. Lin, C.-L. Chen, T.-C. Lin, Y.-A. Chen, J.-Q.
Liu, C.-H. Hung, C.-M. Chao, K.-M. Liu, P.-T. Chou, Chem.
Commun., 2015, 51, 16099.
24. D. T. Gryko, J. Piechowska, M. Galezowski, J. Org. Chem.,
2010, 75, 1297.
active π-conjugated molecules.
Acknowledgements
A
part of this work was technically supported by the
25. K. Takagi, K. Ito, Y. Yamada, T. Nakashima, R. Fukuda, M.
Ehara, D. Takeuchi, Chem. Lett., 2017, 46, 1372.
26. K. Takagi, K. Ito, Y. Yamada, T. Nakashima, R. Fukuda, M.
Ehara, H. Masu, J. Org. Chem., 2017, 82, 12173.
27. During the course of our investigation, Vullev, Lee, and Gryko
and co-workers have reported how to reach intense
luminescence for compounds capable of ESIPT using a family
of 2-(2’-hydroxyphenyl)benzimidazole derivatives. See, K.
Skonieczny, J. Yoo, J. M. Larsen, E. M. Espinoza, M.
Barbasiewicz, V. I. Vullev, C.-H. Lee, D. T. Gryko, Chem. Eur. J.,
2016, 22, 7485.
Nanotechnology Platform Program (Molecule and Material
Synthesis) of the Ministry of Education Culture, Sports, Science and
Technology (MEXT), Japan. A part of this work was financially
supported by and performed under the Research Program of
"Dynamic Alliance for Open Innovation Bridging Human,
Environment and Materials" in "Network Joint Research Center for
Materials and Devices". R.F. acknowledges the financial support
from a Grant-in-Aid for Scientific Research from Japan Society for
the Promotion of Science (JSPS) (26410026). The computations
were partially performed at the Research Center for Computational
Science, Okazaki, Japan.
28. D. R. R. Moreno, G. Giorgi, C. O. Salas, R. A. Tapia, Molecules
2013, 18, 14797.
29. P. Ghosh, R. Subba, Tetrahedron Lett. 2015, 56, 2691.
30. The methoxy proton signal of 1 was unchangeably detected at
4.1 ppm in CDCl3.
Notes and references
31. J. B. Birks, Photophysics of Aromatic Molecules, Wiley, London,
1970.
1.
2.
X. Yang, X, Xu, G. Zhou, J. Mater. Chem. C, 2015, 3, 913–944.
H. N. Kim, W. X. Ren, J. S. Kim, J. Yoon, Chem. Soc. Rev., 2012,
41, 3210–3244.
3.
B. A. D. Neto, P. H. P. R. Carvalho, J. R. Correa, Acc. Chem.
Res., 2015, 48, 1560–1569.
4.
5.
V. S. Padalkar, S. Seki, Chem. Soc. Rev., 2016, 45, 169.
J. Zhao, S. Ji, Y. Chen, H. Guo, P. Yang, Phys. Chem. Chem.
Phys., 2012, 14, 8803.
6.
7.
8.
P. K. Sengupta, M. Kasha, Chem. Phys. Lett., 1979, 68, 382.
D. McMorrow, M. Kasha, J. Phys. Chem., 1984, 88, 2235.
S. Park, J. E. Kwon, S. Y. Park, Phys. Chem. Chem. Phys., 2012,
14, 8878.
9.
S. Park, O.-H. Kwon, Y.-S. Lee, D.-J. Jang, S. Y. Park, J. Phys.
Chem. A, 2007, 111, 9649.
10. S. Park, J. Seo, S. H. Kim, S. Y. Park, Adv. Funct. Mater., 2008,
18, 726.
11. S. Park, O.-H. Kwon, S. Kim, S. Park, M.-G. Choi, M. Cha, S. Y.
Park, D.-J. Jang, J. Am. Chem. Soc., 2005, 127, 10070.
12. S. Park, J. E. Kwon, S. H. Kim, J. Seo, K. Chung, S.-Y. Park, D.-J.
Jang, B. M. Medina, J. Gierschner, S. Y. Park, J. Am. Chem.
Soc., 2009, 131, 14043.
13. T. Mutai, T. Ohkawa, H. Shono, K. Araki, J. Mater. Chem. C,
2016, 4, 3599.
14. T. Mutai, H. Sawatani, T. Shida, H. Shono, K. Araki, J. Org.
Chem., 2013, 78, 2482.
6 | J. Name., 2012, 00, 1-3
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