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  Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties.

Gillanders, F., Giordano, L., Diaz, S. A., Jovin, T. M., & Jares-Erijman, E. A. (2014). Photoswitchable fluorescent diheteroarylethenes: Substituent effects on photochromic and solvatochromic properties. Photochemical and Photobiological Sciences, 33, 603-612. doi:10.1039/C3PP50374G.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0015-3753-7 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0029-BBF1-D
Genre: Journal Article

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Gillanders, F., Author
Giordano, L.1, Author              
Diaz, S. A.1, Author              
Jovin, T. M.1, Author              
Jares-Erijman, E. A., Author
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1Emeritus Group Laboratory of Cellular Dynamics, MPI for biophysical chemistry, Max Planck Society, ou_578629              

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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.

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Language(s): eng - English
 Dates: 2014-01-072014
 Publication Status: Published in print
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 Rev. Method: Peer
 Identifiers: DOI: 10.1039/C3PP50374G
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Title: Photochemical and Photobiological Sciences
Source Genre: Journal
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Pages: - Volume / Issue: 33 Sequence Number: - Start / End Page: 603 - 612 Identifier: -