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Reversible fluorescence modulation based on photochromic diarylethene and fluorescent coumarin

Published online by Cambridge University Press:  31 January 2011

Xiaohai Sheng ,
Aidong Peng ,
Hongbing Fu ,
Jiannian Yao ,
Yuanyuan Liu  and
Yaobing Wang
Xiaohai Sheng
Affiliation:
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, People’s Republic of China; and Graduate School, Chinese Academy of Sciences, Zhongguancun, Beijing 100080, People’s Republic of China
Aidong Peng
Affiliation:
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, People’s Republic of China
Hongbing Fu
Affiliation:
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, People’s Republic of China
Jiannian Yao*
Affiliation:
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, People’s Republic of China
Yuanyuan Liu
Affiliation:
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, People’s Republic of China; and Graduate School, Chinese Academy of Sciences, Zhongguancun, Beijing 100080, People’s Republic of China
Yaobing Wang
Affiliation:
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, People’s Republic of China; and Graduate School, Chinese Academy of Sciences, Zhongguancun, Beijing 100080, People’s Republic of China
*
a)Address all correspondence to this author. e-mail: jnyao@iccas.ac.cn
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Abstract

A fluorescence switch by the photoisomerization of a photochromic compound in CH3CN and in a polymer film using a bistable photochromic (1,2-bis(2-methylbenzo[b]thiophen-3-yl) hexafluorocyclopentene) (BTF6) and a fluorescent 3-(2-benzothiazolyl)-7-(diethylamino) coumarin (coumarin6) was demonstrated. Because only the closed form of BTF6 serves as a fluorescence quencher of coumarin6, and the read (406 nm), write (254 nm), and erase (>500 nm) wavelengths are well-separated, a reversible modulation of the fluorescence of coumarin6 with high contrast and high sensitivity is expected to be realized. This system may represent an alternative to the fluorescence switches that are based on covalent systems in the potentially long-term optical data or image storage schemes utilizing luminescence intensity readout.

Keywords

FilmOrganicPhotoemission
Type
Articles
Information
Journal of Materials Research , Volume 22 , Issue 6 , June 2007 , pp. 1558 - 1563
Copyright
Copyright © Materials Research Society2007

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References

REFERENCES

1Irie, M., Kobatake, S.Horichi, M.: Reversible surface morphology changes of a photochromic diarylethene single crystal by photoirradiation. Science 291, 1769 2001Google Scholar
2Yagi, K., Soong, C.F.Irie, M.: Synthesis of fluorescent diarylethenes having a 2,4,5-triphenylimidazole chromophore. J. Org. Chem. 66, 5419 2001CrossRefGoogle Scholar
3Chen, B., Wang, M., Wu, Y.Tian, H.: Reversible near-infrared fluorescence switch by novel photochromic unsymmetrical-phthalocyanine hybrids based on bisthienylethene. Chem. Commun.1060 2002CrossRefGoogle ScholarPubMed
4Yuan, W.F., Sun, L., Tang, H.H., Wen, Y.Q., Jiang, G.Y., Huang, W.H., Jiang, L., Song, Y.L., Tian, H.Zhu, D.B.: A novel thermally stable spironaphthoxazine and its application in rewritable high density optical data storage. Adv. Mater. 17, 156 2005CrossRefGoogle Scholar
5Cho, H.Kim, E.: Highly fluorescent and photochromic diarylethene oligomer bridged by p-phenylenevinylene. Macromolecules 35, 8684 2002CrossRefGoogle Scholar
6Fernandez, A.Lehn, J-M.: Optical switching and fluorescence modulation in photochromic metal complexes. Adv. Mater. 10, 1519 19983.0.CO;2-R>CrossRefGoogle Scholar
7Osuka, A., Fujikane, D., Shinmori, H., Kobatake, S.Irie, M.: Synthesis and photoisomerization of dithienylethene-bridged diporphyrins. J. Org. Chem. 66, 3913 2001Google Scholar
8Kawai, T., Kim, M-S., Sasaki, T.Irie, M.: Fluorescence switching of photochromic diarylethenes. Opt. Mater. 21, 275 2003CrossRefGoogle Scholar
9Irie, M.: Diarylethenes for memories and switches. Chem. Rev. 100, 1685 2000CrossRefGoogle ScholarPubMed
10Irie, M.: Photoreactive Materials for Ultrahigh-Density Optical Memory,(Elsevier, Amsterdam, 1994)Google Scholar
11Nakamura, S.Irie, M.: Thermally irreversible photochromic systems: A theoretical study. J. Org. Chem. 53, 6136 1988CrossRefGoogle Scholar
12Nakayama, Y., Hayashi, K.Irie, M.: Thermally irreversible photochromic systems: Reversible photocyclization of 1,2-diselenenylethene and 1,2-diindolylethene derivatives. J. Org. Chem. 55, 2592 1990CrossRefGoogle Scholar
13Hanazawa, M., Sumiya, R., Horikawa, Y.Irie, M.: Thermally irreversible photochromic system: Reversible photocyclization of 1,2-bis(2-methylbenzo[b]thiophen-3-yl)perfluorocyclocoalkene derivatives. J. Chem. Soc., Chem. Commun. 3, 206 1992Google Scholar
14Myles, A.J.Branda, N.R.: 1,2-Dithienylethene photochromes memory. Adv. Funct. Mater. 12, 167 20023.0.CO;2-M>CrossRefGoogle Scholar
15Tian, H.Yang, S.J.: Recent processes on diarylethene based photochromic switches. Chem. Soc. Rev. 33, 85 2004CrossRefGoogle Scholar
16Irie, M., Fukaminato, T., Sasaki, T., Tamai, N.Kawai, T.: A digital fluorescent molecular photoswitch. Nature 420, 759 2002CrossRefGoogle ScholarPubMed
17Norsten, T.B.Branda, N.R.: Photoregulation of fluorescence in a porphyrinic dithienylethene photochrome. J. Am. Chem. Soc. 123, 1784 2001CrossRefGoogle Scholar
18Kawai, T., Sasaki, T.Irie, M.: A photoresponsive laser dye containing photochromic dithienylethene units. Chem. Commun.711 2001CrossRefGoogle Scholar
19Jiang, G.Y., Wang, S., Yuan, W.F., Jiang, L., Song, Y.L., Tian, H.Zhu, D.B.: Highly fluorescent contrast for rewritable optical storage based on photochromic bisthienylethene-bridged naphthalimide dimer. Chem. Mater. 18(2), 235 2006CrossRefGoogle Scholar
20Fukaminato, T., Sasaki, T., Kawai, T., Tamai, N.Irie, M.: Digital photoswitching of fluorescence based on the photochromism of diarylethene derivatives at a single-molecule level. J. Am. Chem. Soc. 126, 14843 2004Google Scholar
21Lim, S.J., An, B.K., Jung, S.D., Chung, M-A.Park, S.Y.: Photoswitchable organic nanoparticles and a polymer film employing multifunctional molecules with enhanced fluorescence emission and bistable photochromism. Angew. Chem., Int. Ed. Engl. 43, 6346 2004Google Scholar
22Norsten, T.B.Branda, N.R.: Axially coordinated porphyrinic photochromes for non-destructive information processing. Adv. Mater. 13, 347 20013.0.CO;2-9>CrossRefGoogle Scholar
23Chen, Y.Xie, N.: Modulation of a fluorescent switch based on a controllable photochromic diarylethene shutter. J. Mater. Chem. 15, 3229 2005Google Scholar
24Tomasula, M., Giordani, S.Raymo, F.M.: Fluorescence modulation in polymer bilayers containing fluorescent and photochromic dopants. Adv. Funct. Mater. 15, 787 2005CrossRefGoogle Scholar
25Kozlov, D.V.Castellano, F.N.: Photochemically reversible luminescence lifetime switching in metal-organic systems. J. Phys. Chem. A. 108, 10619 2004Google Scholar
26Murase, S., Teramoto, M., Furukawa, H., Miyashita, Y.Horie, K.: Photochemically induced fluorescence control with intermolecular energy transfer from a fluorescent dye to a photochromic diarylethene in a polymer film. Macromolecules 36, 964 2003CrossRefGoogle Scholar
27Reynolds, G.A.Drexhage, K.H.: New coumarin dyes with rigidized structure for flashlamp-pumped dye lasers. Opt. Commun. 13, 222 1975CrossRefGoogle Scholar
28Jones, G. II, Jackson, W.R., Choi, C.Y., Bergmark, W.R.: Solvent effects on emission yield and lifetime for coumarin laser dyes. Requirements for a rotatory decay mechanism. J. Phys. Chem. 89(2), 294 1985Google Scholar
29Kim, S.Park, S.Y.: Photochemically gated protonation effected by intramolecular hydrogen bonding: Towards stable fluorescence imaging in polymer films. Adv. Mater. 15, 1341 2003CrossRefGoogle Scholar
30Trouts, T.D., Tyson, D.S., Phol, R., Kozlov, D.V., Waldron, A.G.Castellano, F.N.: Dinuclear metal-organic material for binary optical recording. Adv. Funct. Mater. 13, 398 2003Google Scholar
31Turro, N.J.: Modern Molecular Photochemistry(Benjamin/Cummings Publishing Co., Menlo Park, CA, 1978) p. 299Google Scholar