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http://dx.doi.org/10.5012/bkcs.2012.33.11.3740

Synthesis and Characterizations of Bis-Spiropyran Derivatives  

Lee, Sungmin (Department of Chemistry, Research Institute for Natural Sciences, and Institute of Nano Science and Technology)
Ji, Seungwook (Department of Chemistry, Research Institute for Natural Sciences, and Institute of Nano Science and Technology)
Kang, Youngjong (Department of Chemistry, Research Institute for Natural Sciences, and Institute of Nano Science and Technology)
Publication Information
Bulletin of the Korean Chemical Society / v.33, no.11, 2012 , pp. 3740-3744 More about this Journal
Abstract
We synthesized three different derivatives of bis-spiropyran using simple organic reactions with high yields. BSP1, a derivative of bis-spiropyran having a connection at the position 6' and BSP2, a derivative of bis-spiropyran having a connection at the position 5 and BSP3, a derivative of bis-spiropyran containing a dithienylethene group between two spiropyran moieties were synthesized. The optical properties of BSPs were characterized. UV-Vis spectra showed that BSPs exhibit reversible photo-isomerization and the efficiency of photo-isomerization is highly dependent on the position of nitro group. BSPs having nitro group at para position of hydroxy group showed the higher efficiency of photo-isomerization that the one having nitro group at ortho position. The optical microscope images obtained under ultraviolet or visible light exposure demonstrated that the formation of nanorods can be reversibly controlled by optical signal.
Keywords
Oligo-spiropyran; Photochromic; Photo-induced aggregation; Nanorods;
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1 Uznanski, P. Langmuir 2003, 19, 1919.   DOI   ScienceOn
2 Fukushima, K.; Vandenbos, A. J.; Fujiwara, T. Chem. Mater. 2007, 19, 644.   DOI   ScienceOn
3 Shao, N.; Jin, J.; Wang, H.; Zheng, J.; Yang, R.; Chan, W.; Abliz, Z. J. Am. Chem. Soc. 2009, 132, 725.
4 Liu, H. B.; Wang, M.; Wang, Y.; Wang, L.; Sun, L. C. Synth. Commun. 2010, 40, 1074.   DOI   ScienceOn
5 Klotz, E. J. F.; Claridge, T. D. W.; Anderson, H. L. J. Am. Chem. Soc. 2006, 128, 15374.   DOI   ScienceOn
6 Osuka, A.; Fujikane, D.; Shinmori, H.; Kobatake, S.; Irie, M. J. Org. Chem. 2001, 66, 3913.   DOI   ScienceOn
7 Lee, P. H.; Seomoon, D.; Lee, K. Org. Lett. 2005, 7, 343.   DOI   ScienceOn
8 Lee, K.; Lee, P. H. Tetrahedron Lett. 2008, 49, 4302.   DOI   ScienceOn
9 Keum, S. R.; Hur, M. S.; Kazmaier, P. M.; Buncel, E. Can. J. Chem. 1991, 69, 1940.   DOI
10 Keum, S. R.; Lee, J. H.; Seok, M. K.; Yoon, C. M. Bull. Korean Chem. Soc. 1994, 15, 275.
11 Keum, S. R.; Lee, J. H.; Seok, M. K. Dyes Pigm. 1994, 25, 21.   DOI   ScienceOn
12 Keum, S. R.; Lim, S. S.; Min, B. H.; Kazmaier, P. M.; Buncel, E. Dyes Pigm. 1996, 30, 225.   DOI   ScienceOn
13 Keum, S. R.; Choi, Y. K.; Kim, S. H.; Yoon, C. M. Dyes Pigm. 1999, 41, 41.   DOI   ScienceOn
14 Cho, Y. J.; Rho, K. Y.; Kim, S. H.; Keum, S. R.; Yoon, C. M. Dyes Pigm. 1999, 44, 19.   DOI   ScienceOn
15 Keum, S. R.; Choi, Y. K.; Lee, M. J.; Kim, S. H. Dyes Pigm. 2001, 50, 171.   DOI   ScienceOn
16 Suzuki, T.; Kawata, Y.; Kahata, S.; Kato, T. Chem. Commun. 2003, 2004.
17 Suzuki, T.; Kato, T.; Shinozaki, H. Chem. Commun. 2004, 2036.
18 Zhu, M. Q.; Zhu, L.; Han, J. J.; Wu, W.; Hurst, J. K.; Li, A. D. Q. J. Am. Chem. Soc. 2006, 128, 4303.   DOI   ScienceOn
19 Fries, K. H.; Driskell, J. D.; Samanta, S.; Locklin, J. Anal. Chem. 2010, 82, 3306.   DOI   ScienceOn
20 Fries, K.; Samanta, S.; Orski, S.; Locklin, J. Chem. Commun. 2008, 6288.
21 Suzuki, T.; Hirahara, Y.; Bunya, K.; Shinozaki, H. J. Mater. Chem. 2010, 20, 2773.   DOI   ScienceOn
22 Brown, G. H. Photochromism; Wiley Interscience: New York, 1971.
23 Durr, H.; Bouas-Laurent, H. Photochromism: Molecules and Systems; Elsevier Science: Amsterdam, 2003
24 Berkovic, G.; Krongauz, V.; Weiss, V. Chem. Rev. 2000, 100, 1741.   DOI   ScienceOn
25 Davis, D. A.; Hamilton, A.; Yang, J.; Cremar, L. D.; Van Gough, D.; Potisek, S. L.; Ong, M. T.; Braun, P. V.; Martínez, T. J.; White, S. R. Nature 2009, 459, 68.   DOI   ScienceOn
26 Evans, R. A.; Hanley, T. L.; Skidmore, M. A.; Davis, T. P.; Such, G. K.; Yee, L. H.; Ball, G. E.; Lewis, D. A. Nat. Mater. 2005, 4, 249.   DOI   ScienceOn
27 Tork, A.; Boudreault, F.; Roberge, M.; Ritcey, A. M.; Lessard, R. A.; Galstian, T. V. Appl. Opt. 2001, 40, 1180.   DOI
28 Such, G.; Evans, R. A.; Yee, L. H.; Davis, T. P. J. Macromol. Sci., Polym. Rev. 2003, 43, 547.   DOI   ScienceOn
29 Menju, A.; Hayashi, K.; Irie, M. Macromolecules 1981, 14, 755.   DOI
30 Konak, C.; Rathi, R. C.; Kopecková, P.; Kopecek, J. Macromolecules 1997, 30, 5553.   DOI   ScienceOn