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  Highly solvatochromic 7-aryl-3-hydroxychromones.

Giordano, L., Shvadchak, V. V., Fauerbach, J. A., Jares-Erijman, E. A., & Jovin, T. M. (2012). Highly solvatochromic 7-aryl-3-hydroxychromones. Journal of Physical Chemistry Letters, 3, 1011-1016. doi:10.1021/jz3002019.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-000F-83B6-5 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0027-C64B-0
Genre: Journal Article

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1443687.pdf (Publisher version), 347KB
 
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 Creators:
Giordano, L.1, Author              
Shvadchak, V. V.1, Author              
Fauerbach, J. A., Author
Jares-Erijman, E. A., Author
Jovin, T. M.1, Author              
Affiliations:
1Emeritus Group Laboratory of Cellular Dynamics, MPI for biophysical chemistry, Max Planck Society, ou_578629              

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 Abstract: Introduction of the dialkylaminophenyl group in position 7 of 3 ‑ hydroxychromone changes the orientation of the excited-state dipole moment and leads to superior solvatochromic properties (>170 nm emission shift in aprotic media). The excited-state intramolecular proton-transfer (ESIPT) reaction of 7-aryl-3-hydrox- ychromones is almost completely inhibited in most solvents. Methylation of the 3-OH abolishes ESIPT completely and also leads to improved photostability. The probes exhibit a ∼ 100-fold increase in fluorescence intensity and large Stokes shifts upon binding to membranes, reflecting differences in membrane phase and charge by a >40 nm spread in the emission band position.

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Language(s): eng - English
 Dates: 2012-03-202012
 Publication Status: Published in print
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 Rev. Method: Peer
 Identifiers: DOI: 10.1021/jz3002019
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Title: Journal of Physical Chemistry Letters
Source Genre: Journal
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Pages: - Volume / Issue: 3 Sequence Number: - Start / End Page: 1011 - 1016 Identifier: -