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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

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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