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Copyright (c) 2014 Rabab Sharaf Jassas1, Samy Abdullah El-Daly1, Abdullah M. Asiri1, Salman A Khan1
This work is licensed under a Creative Commons Attribution 4.0 International License.
Excitation Energy Transfer from Rhodamine 6G to Photochromic Fulgide
Corresponding Author(s) : Rabab Sharaf Jassas1
Asian Journal of Chemistry,
Vol. 26 No. 23 (2014)
Abstract
In this work, a new fluorescence photoswitching system consisting of fulgide as a photochrome and rhodamine 6G as a fluorophor was designed and studied in methanol, dichloromethane and dioxane. The spectra of both the closed form of fulgide and rhodamine 6G were overlapped. Since the fulgide exhibited non-fluorescence, the emission spectra of blended system were attributed to rhodamine 6G only. The intensity of the fluorescence emission spectra of the rhodamine 6G was modified by the photochromism of fulgide upon irradiation with UV light at different time in methanol, dichloromethane and dioxane. The blended system exhibited quenching in fluorescence emission spectra in different solvents.
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- B.L. Feringa, Molecular Switches, New York (2001).
- H. Dürr and H. Bous-Laurent, Photochromism: Molecules and Systems, Amsterdam: Elsevier (1990).
- G.H. Brown, Photochromism; Molecules and Systems. New York: Wiley Interscience (1971).
- M. Irie, Photo-reactive Materials for Ultrahigh Density Optical Memory: MITI Research and Development Program on Basic Technologies for Future Industries (1994).
- S. Kawai, T. Nakashima, K. Atsumi, T. Sakai, M. Harigai, Y. Imamoto, H. Kamikubo, M. Kataoka and T. Kawai, Chem. Mater., 19, 3479 (2007).
- T. Tsujioka and M. Irie, J. Photochem. Photobiol. Photochem. Rev., 11, 1 (2010).
- H. Stobbe, Ber. Dtsch. Chem. Ges., 38, 3673 (1905).
- A. Santiago and R.S. Becker, J. Am. Chem. Soc., 90, 3654 (1968).
- H.G. Heller and J.R. Langan, J. Chem. Soc. Perkin Trans. II, 341 (1981).
- H.G.Heller and S.Oliver, J. Chem. Soc. Perkin Trans. I, 197 (1981).
- Y. Yokoyama and K. Takahashi, Chem. Lett., 25, 1037 (1996).
- I. Willner, S. Rubin, J. Wonner, F. Effenberger and P. Baeuerle, J. Am. Chem. Soc., 114, 3150 (1992).
- Y. Yokoyama, Chem. Rev., 100, 1717 (2000).
- M.W. Berns, T. Krasieva, C.-H. Sun, A. Dvornikov and P.M. Rentzepis, J. Photochem. Photobiol. B, 75, 51 (2004).
- G.H. Dorion and A. F. Wiebe, Photochromism: Optical and Photographic Applications, Focal Press (1970).
- A.M. Asiri, S.A. El-Daly and S.A. Khan, Spectrochim. Acta A, 95, 679 (2012).
- H. Gross, H. Dürr and W. Rettig, J. Photochem., 26, 165 (1984).
- M. Irie, K. Sakemura, M. Okinaka and K. Uchida, J. Org. Chem., 60, 8305 (1995).
- C. Weber, F. Rustemeyer and H. Dürr, Adv. Mater., 10, 1348 (1998).
- M.A.L. Sheepwash, R.H. Mitchell and C. Bohne, J. Am. Chem. Soc., 124, 4693 (2002).
- A. Fernández-Acebes and J.-M. Lehn, Chem. Eur. J., 5, 3285 (1999).
- M. Irie, T. Fukaminato, T. Sasaki, N. Tamai and T. Kawai, Nature, 420, 759 (2002).
- Y. Liang, A.S. Dvornikov and P.M. Rentzepis, Opt. Commun., 223, 61 (2003).
- A. Dvornikov, Y. Liang and P. Rentzepis, J. Mater. Chem., 15, 1072 (2005).
- J.L. Bahr, G. Kodis, L. de la Garza, S. Lin, A.L. Moore, T.A. Moore and D. Gust, J. Am. Chem. Soc., 123, 7124 (2001).
- H. Görner, Phys. Chem. Chem. Phys., 3, 416 (2001).
- M. Frigoli, C. Welch and G.H. Mehl, J. Am. Chem. Soc., 126, 15382 (2004).
- M. Jin, R. Lu, C.Y. Bao, T.H. Xu and Y.Y. Zhao, Opt. Mater. (Amst), 26, 85 (2004).
- F.M. Raymo and M. Tomasulo, J. Phys. Chem. A, 109, 7343 (2005).
- S. Pu, D. Jiang, W. Liu, G. Liu and S. Cui, J. Mater. Chem., 22, 3517 (2012).
- T. Koshido, T. Kawai and K. Yoshino, Synth. Met., 73, 257 (1995).
- H. Choi, B.-S. Ku, S.-R. Keum, S. Ook Kang and J. Ko, Tetrahedron, 61, 3719 (2005).
- D.V. Kozlov and F.N. Castellano, J. Phys. Chem. A, 108, 10619 (2004).
- J.C. Crano and R.J. Guglielmetti, Organic Photochromic and Thermochromic Compounds - Main Photochromic Families, Springer (1999).
- E.-Z.M. Ebeid, R.M. Issa, M.M. Ghoneim and S.A. El-Daly, J. Chem. Soc., Faraday Trans. I, 82, 909 (1986).
- S.L. Murov, Handbook of Photochemistry, Marcel Dekker, INC. New York, vol. 13, p. 119 (973).
References
B.L. Feringa, Molecular Switches, New York (2001).
H. Dürr and H. Bous-Laurent, Photochromism: Molecules and Systems, Amsterdam: Elsevier (1990).
G.H. Brown, Photochromism; Molecules and Systems. New York: Wiley Interscience (1971).
M. Irie, Photo-reactive Materials for Ultrahigh Density Optical Memory: MITI Research and Development Program on Basic Technologies for Future Industries (1994).
S. Kawai, T. Nakashima, K. Atsumi, T. Sakai, M. Harigai, Y. Imamoto, H. Kamikubo, M. Kataoka and T. Kawai, Chem. Mater., 19, 3479 (2007).
T. Tsujioka and M. Irie, J. Photochem. Photobiol. Photochem. Rev., 11, 1 (2010).
H. Stobbe, Ber. Dtsch. Chem. Ges., 38, 3673 (1905).
A. Santiago and R.S. Becker, J. Am. Chem. Soc., 90, 3654 (1968).
H.G. Heller and J.R. Langan, J. Chem. Soc. Perkin Trans. II, 341 (1981).
H.G.Heller and S.Oliver, J. Chem. Soc. Perkin Trans. I, 197 (1981).
Y. Yokoyama and K. Takahashi, Chem. Lett., 25, 1037 (1996).
I. Willner, S. Rubin, J. Wonner, F. Effenberger and P. Baeuerle, J. Am. Chem. Soc., 114, 3150 (1992).
Y. Yokoyama, Chem. Rev., 100, 1717 (2000).
M.W. Berns, T. Krasieva, C.-H. Sun, A. Dvornikov and P.M. Rentzepis, J. Photochem. Photobiol. B, 75, 51 (2004).
G.H. Dorion and A. F. Wiebe, Photochromism: Optical and Photographic Applications, Focal Press (1970).
A.M. Asiri, S.A. El-Daly and S.A. Khan, Spectrochim. Acta A, 95, 679 (2012).
H. Gross, H. Dürr and W. Rettig, J. Photochem., 26, 165 (1984).
M. Irie, K. Sakemura, M. Okinaka and K. Uchida, J. Org. Chem., 60, 8305 (1995).
C. Weber, F. Rustemeyer and H. Dürr, Adv. Mater., 10, 1348 (1998).
M.A.L. Sheepwash, R.H. Mitchell and C. Bohne, J. Am. Chem. Soc., 124, 4693 (2002).
A. Fernández-Acebes and J.-M. Lehn, Chem. Eur. J., 5, 3285 (1999).
M. Irie, T. Fukaminato, T. Sasaki, N. Tamai and T. Kawai, Nature, 420, 759 (2002).
Y. Liang, A.S. Dvornikov and P.M. Rentzepis, Opt. Commun., 223, 61 (2003).
A. Dvornikov, Y. Liang and P. Rentzepis, J. Mater. Chem., 15, 1072 (2005).
J.L. Bahr, G. Kodis, L. de la Garza, S. Lin, A.L. Moore, T.A. Moore and D. Gust, J. Am. Chem. Soc., 123, 7124 (2001).
H. Görner, Phys. Chem. Chem. Phys., 3, 416 (2001).
M. Frigoli, C. Welch and G.H. Mehl, J. Am. Chem. Soc., 126, 15382 (2004).
M. Jin, R. Lu, C.Y. Bao, T.H. Xu and Y.Y. Zhao, Opt. Mater. (Amst), 26, 85 (2004).
F.M. Raymo and M. Tomasulo, J. Phys. Chem. A, 109, 7343 (2005).
S. Pu, D. Jiang, W. Liu, G. Liu and S. Cui, J. Mater. Chem., 22, 3517 (2012).
T. Koshido, T. Kawai and K. Yoshino, Synth. Met., 73, 257 (1995).
H. Choi, B.-S. Ku, S.-R. Keum, S. Ook Kang and J. Ko, Tetrahedron, 61, 3719 (2005).
D.V. Kozlov and F.N. Castellano, J. Phys. Chem. A, 108, 10619 (2004).
J.C. Crano and R.J. Guglielmetti, Organic Photochromic and Thermochromic Compounds - Main Photochromic Families, Springer (1999).
E.-Z.M. Ebeid, R.M. Issa, M.M. Ghoneim and S.A. El-Daly, J. Chem. Soc., Faraday Trans. I, 82, 909 (1986).
S.L. Murov, Handbook of Photochemistry, Marcel Dekker, INC. New York, vol. 13, p. 119 (973).