Abstract:
Photoswitchable fluorescent diheteroarylethenes are promising candidates for applications in super-resolution molecular localization fluorescence microscopy thanks to their high quantum yields and fatigue-resistant photoswitching characteristics. We have studied the effect of varying substituents on the photophysical properties of six sulfone derivatives of diheteroarylethenes, which display fluorescence in one (closed form) of two thermally stable photochromic states. Electron-donating substituents displace the absorption and emission spectra towards the red without substantially affecting the fluorescence quantum yields. Furthermore, ethoxybromo, a very electron-donating substituent, stabilizes the excited state of the closed isomer to the extent of almost entirely inhibiting its cycloreversion. Multi-parameter Hammett correlations indicate a relationship between the emission maxima and electron-donating character, providing a useful tool in the design of future photochromic molecules. Most of the synthesized compounds exhibit small bathochromic shifts and shorter fluorescence lifetimes with an increase in solvent polarity. However, the ethoxybromo-substituted fluorescent photochrome is unique in its strong solvatochromic behaviour, constituting a photoactivatable (photochromic), fluorescent and highly solvatochromic small organic compound. The Catalán formalism identified solvent dipolarity as the principal basis of the solvatochromism, reflecting the highly polarized nature of this molecule. © The Royal Society of Chemistry and Owner Societies.
Registro:
Documento: |
Artículo
|
Título: | Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties |
Autor: | Gillanders, F.; Giordano, L.; Díaz, S.A.; Jovin, T.M.; Jares-Erijman, E.A. |
Filiación: | Laboratory of Cellular Dynamics, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Göttingen, Germany Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires CIHIDECAR CONICET, 1428 Buenos Aires, Argentina Centro de Investigaciones en Bionanociencias (CIBON), CONICET, Godoy Cruz 2390, 1425 Capital Federal, Argentina
|
Palabras clave: | 1,4-dioxane; acetic acid derivative; acetic acid ethyl ester; dioxane; dioxane derivative; fluorescent dye; heptane; methanol; solvent; absorption; article; chemical structure; chemistry; electron; fluorescence; isomerism; photochemistry; spectrofluorometry; statistical model; synthesis; Absorption; Acetates; Dioxanes; Electrons; Fluorescence; Fluorescent Dyes; Heptanes; Isomerism; Linear Models; Methanol; Molecular Structure; Photochemical Processes; Solvents; Spectrometry, Fluorescence |
Año: | 2014
|
Volumen: | 13
|
Número: | 3
|
Página de inicio: | 603
|
Página de fin: | 612
|
DOI: |
http://dx.doi.org/10.1039/c3pp50374g |
Título revista: | Photochemical and Photobiological Sciences
|
Título revista abreviado: | Photochem. Photobiol. Sci.
|
ISSN: | 1474905X
|
CODEN: | PPSHC
|
CAS: | acetic acid ethyl ester, 141-78-6; dioxane, 123-91-1; heptane, 142-82-5, 3356-67-0; methanol, 67-56-1
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v13_n3_p603_Gillanders |
Referencias:
- Hell, S.W., (2007) Science, 316, pp. 1153-1158
- Huang, B., (2010) Curr. Opin. Chem. Biol., 14, pp. 10-14
- Müller, T., Schumann, C., Kraegeloh, A., (2012) ChemPhysChem, 13, pp. 1986-2000
- Shao, L., Kner, P., Rego, E.H., Gustafsson, M.G.L., (2011) Nat. Methods, 12, pp. 1044-1046
- York, A.G., Parekh, S.H., Dalle Nogare, D., Fischer, R.S., Temprine, K., Mione, M., Chitnis, A.B., Shroff, H., (2012) Nat. Methods, 9, pp. 749-754
- Lidke, D.S., Lidke, K.A., (2012) J. Cell Sci., 125, pp. 2571-2580
- Dertinger, T., Colyer, R., Iyer, G., Weiss, S., Enderlein, J., (2009) Proc. Natl. Acad. Sci. U. S. A., 106, pp. 22287-22292
- Müller, C.B., Enderlein, J., (2010) Phys. Rev. Lett., 104, p. 198101
- Vogelsang, J., Cordes, T., Forthmann, C., Steinhauer, C., Tinnefeld, P., (2010) Nano Lett., 10, pp. 672-679
- Owen, D.M., Williamson, D.J., Magenau, A., Gaus, K., (2012) Nat. Commun., 3, p. 1256
- Lakadamyali, M., Babcock, H., Bates, M., Zhuang, X., Lichtman, J., (2012) PloS One, 7, p. 30826
- Henriques, R., Griffiths, C., Hesper Rego, E., Mhlanga, M.M., (2011) Biopolymers, 95, pp. 322-331
- Ha, T., Tinnefeld, P., (2012) Annu. Rev. Phys. Chem., 63, pp. 595-617
- Lord, S.J., Conley, N.R., Lee, H.-L.D., Nishimura, S.Y., Pomerantz, A.K., Willets, K.A., Lu, Z., Moerner, W.E., (2009) ChemPhysChem, 10, pp. 55-65
- Bourgeois, D., Regis-Faro, A., Adam, V., (2012) Biochem. Soc. Trans., 40, pp. 531-538
- Finan, K., Flottmann, B., Heilemann, M., (2013) Methods in Molecular Biology, 950. , in, ed. A. A. Sousa and M. J. Kruhlak, Humana Press, Totowa, NJ, 131-151
- Carling, C.-J., Boyer, J.-C., Branda, N.R., (2012) Org. Biomol. Chem., 10, pp. 6159-6168
- May, F., Peter, M., Hütten, A., Prodi, L., Mattay, J., (2012) Chem.-Eur. J., 18, pp. 814-821
- Klein, T., Van De Linde, S., Sauer, M., (2012) ChemBioChem, 13, pp. 1861-1863
- Kolmakov, K., Wurm, C., Sednev, M.V., Bossi, M.L., Belov, V.N., Hell, S.W., (2012) Photochem. Photobiol. Sci., 11, pp. 522-532
- Schäfer, P., Van De Linde, S., Lehmann, J., Sauer, M., Doose, S., (2013) Anal. Chem., 85, pp. 3393-3400
- Schwering, M., Kiel, A., Kurz, A., Lymperopoulos, K., Sprödefeld, A., Krämer, R., Herten, D.-P., (2011) Angew. Chem., Int. Ed., 50, pp. 2940-2945
- Hagen, G.M., Caarls, W., Lidke, K.A., De Vries, A.H.B., Fritsch, C., Barisas, B.G., Arndt-Jovin, D.J., Jovin, T.M., (2009) Micros. Res. Tech., 72, pp. 431-440
- Giordano, L., Jovin, T.M., Irie, M., Jares-Erijman, E.A., (2002) J. Am. Chem. Soc., 124, pp. 7481-7489
- Díaz, S.A., Giordano, L., Jovin, T.M., Jares-Erijman, E.A., (2012) Nano Lett., 12, pp. 3537-3544
- Yan, Y., Marriott, M.E., Petchprayoon, C., Marriott, G., (2011) Biochem. J., 433, pp. 411-422
- Uno, K., Niikura, H., Morimoto, M., Ishibashi, Y., Miyasaka, H., Irie, M., (2011) J. Am. Chem. Soc., 133, pp. 13558-13564
- Qiu, J., Wang, L., Liu, M., Shen, Q., Tang, J., (2011) Tetrahedron Lett., 52, pp. 6489-6491
- Jeong, Y.-C., Yang, S.I., Ahn, K.-H., Kim, E., (2005) Chem. Commun., 19, pp. 2503-2505
- Liu, G., Pu, S., Wang, X., (2010) Tetrahedron, 66, pp. 8862-8871
- Pu, S., Wang, R., Liu, G., Liu, W., Cui, S., Yan, P., (2012) Dyes Pigm., 94, pp. 195-206
- Morimitsu, K., Kobatake, S., (2005) Mol. Cryst. Liq. Cryst., 431, pp. 151-154
- Pu, S., Fan, C., Miao, W., Liu, G., (2010) Dyes Pigm., 84, pp. 25-35
- Irie, M., Sakemura, K., Okinaka, M., Uchida, K., (1995) J. Org. Chem., 60, pp. 8305-8309
- Takagi, Y., Kunishi, T., Katayama, T., Ishibashi, Y., Miyasaka, H., Morimoto, M., Irie, M., (2012) Photochem. Photobiol. Sci., 11, pp. 1661-1665
- Hansch, C., Leo, A., Taft, W., (1991) Chem. Rev., 91, pp. 165-195
- Hammett, L.P., (1937) Struct. React. Benzene Compounds, 59, pp. 96-103
- Neuvonen, H., Neuvonen, K., Koch, A., Kleinpeter, E., Pasanen, P., (2002) J. Org. Chem., 67, pp. 6995-7003
- Contreras, R., Andrés, J., Domingo, L.R., Castillo, R., Pérez, P., (2005) Tetrahedron, 61, pp. 417-422
- http://riodb01.ibase.aist.go.jp/sbds/, Spectral Database for Organic Compounds (National Institute of Advanced Industrial Science and Technology) (accessed November 29, 2012); Cui, X., Zhang, Y., Shi, F., Deng, Y., (2011) Chemistry, 17, pp. 1021-1028
- Guillaumont, D., Kobayashi, T., Kanda, K., Miyasaka, H., Uchida, K., Kobatake, S., Shibata, K., Irie, M., (2002) J. Phys. Chem. A, 106, pp. 7222-7227
- Asano, Y., Murakami, A., Kobayashi, T., Goldberg, A., Guillaumont, D., Yabushita, S., Irie, M., Nakamura, S., (2004) J. Am. Chem. Soc., 126, pp. 12112-12120
- Boggio-Pasqua, M., Ravaglia, M., Bearpark, M.J., Garavelli, M., Robb, M.A., (2003) J. Phys. Chem. A, 107, pp. 11139-11152
- Ishibashi, Y., Umesato, T., Kobatake, S., Irie, M., Miyasaka, H., (2012) J. Phys. Chem. C, 116, pp. 4862-4869
- Polyakova, S.M., Belov, V.N., Bossi, M.L., Hell, S.W., (2011) Eur. J. Org. Chem., pp. 3301-3312
- Reichardt, C., (1994) Chem. Rev., 94, pp. 2319-2358
- Catalán, J., (2009) J. Phys. Chem. B, 113, pp. 5951-5960
- Giordano, L., Shvadchak, V.V., Fauerbach, J.A., Jares-Erijman, E.A., Jovin, T.M., (2012) J. Phys. Chem. Lett., 3, pp. 1011-1016
- Jeong, Y.-C., Park, D.G., Lee, I.S., Yang, S.I., Ahn, K.-H., (2009) J. Mater. Chem., 19, pp. 97-103
- Fery-Forgues, S., Fayet, J.-P., Lopez, A., (1993) J. Photochem. Photobiol., A: Chem., 70, pp. 229-243
- Lakowicz, J.R., (1999) Principles of Fluorescence Spectroscopy, , Kluwer Academic/Plenum Publishers, New York, U.S.A., 2nd edn
- Kobatake, S., Terakawa, Y., Imagawa, H., (2009) Tetrahedron, 65, pp. 6104-6108
- Jeong, Y.-C., Yang, S.I., Kim, E., Ahn, K.-H., (2006) Tetrahedron, 62, pp. 5855-5861
Citas:
---------- APA ----------
Gillanders, F., Giordano, L., Díaz, S.A., Jovin, T.M. & Jares-Erijman, E.A.
(2014)
. Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties. Photochemical and Photobiological Sciences, 13(3), 603-612.
http://dx.doi.org/10.1039/c3pp50374g---------- CHICAGO ----------
Gillanders, F., Giordano, L., Díaz, S.A., Jovin, T.M., Jares-Erijman, E.A.
"Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties"
. Photochemical and Photobiological Sciences 13, no. 3
(2014) : 603-612.
http://dx.doi.org/10.1039/c3pp50374g---------- MLA ----------
Gillanders, F., Giordano, L., Díaz, S.A., Jovin, T.M., Jares-Erijman, E.A.
"Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties"
. Photochemical and Photobiological Sciences, vol. 13, no. 3, 2014, pp. 603-612.
http://dx.doi.org/10.1039/c3pp50374g---------- VANCOUVER ----------
Gillanders, F., Giordano, L., Díaz, S.A., Jovin, T.M., Jares-Erijman, E.A. Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties. Photochem. Photobiol. Sci. 2014;13(3):603-612.
http://dx.doi.org/10.1039/c3pp50374g