Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties
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...
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paper:paper_1474905X_v13_n3_p603_Gillanders2023-06-08T16:17:40Z Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties Giordano, Luciana 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 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. Fil:Giordano, L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2014 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v13_n3_p603_Gillanders http://hdl.handle.net/20.500.12110/paper_1474905X_v13_n3_p603_Gillanders |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Giordano, Luciana Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties |
| topic_facet |
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 |
| description |
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. |
| author |
Giordano, Luciana |
| author_facet |
Giordano, Luciana |
| author_sort |
Giordano, Luciana |
| title |
Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties |
| title_short |
Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties |
| title_full |
Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties |
| title_fullStr |
Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties |
| title_full_unstemmed |
Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties |
| title_sort |
photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties |
| publishDate |
2014 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v13_n3_p603_Gillanders http://hdl.handle.net/20.500.12110/paper_1474905X_v13_n3_p603_Gillanders |
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AT giordanoluciana photoswitchablefluorescentdiheteroarylethenessubstituenteffectsonphotochromicandsolvatochromicproperties |
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