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Water-soluble cruciforms and distyrylbenzenes: synthesis, characterization, and pH-dependent amine-sensing properties

Three water-soluble fluorescent aldehyde-substituted distyrylbenzene derivatives were prepared using Heck or Horner methodologies. Water solubility was achieved through the addition of branched oligoethylene glycol side chains; these are attached via an ether bridge to the aromatic nucleus. The alde...

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Bibliographic Details
Main Authors: Freudenberg, Jan (Author) , Kumpf, Jan (Author) , Sauter, Eric (Author) , Wörner, Svenja (Author) , Brödner, Kerstin (Author) , Dreuw, Andreas (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: April 15, 2013
In: The journal of organic chemistry
Year: 2013, Volume: 78, Issue: 10, Pages: 4949-4959
ISSN:1520-6904
DOI:10.1021/jo400576y
Online Access:Verlag, Volltext: http://dx.doi.org/10.1021/jo400576y
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Author Notes:Jan Freudenberg, Jan Kumpf, Vera Schäfer, Eric Sauter, Svenja J. Wörner, Kerstin Brödner, Andreas Dreuw, and Uwe H. F. Bunz
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Summary:Three water-soluble fluorescent aldehyde-substituted distyrylbenzene derivatives were prepared using Heck or Horner methodologies. Water solubility was achieved through the addition of branched oligoethylene glycol side chains; these are attached via an ether bridge to the aromatic nucleus. The aldehydes are almost nonfluorescent in water, but addition of primary amines turns the fluorescence on; formation of imines results. Control of the basicity of the media allows further discrimination of the analytes employed. 1,3-Diaminopropane reacts with these aldehydes. Instead of an imine, a brightly fluorescent aminal forms. Amino acids are almost always nonreactive toward these aldehydes. Exceptions are lysine and cysteine, which form an imine and a thioaminal, respectively, discreating the aldehyde unit under fluorescence turn-on in water. The detection limit and time of completion of the sensing event were evaluated. Dialdehydes 3 and 16 were comparable on both counts. The cross-shaped 16 did react approximately twice as quickly with 1,3-diaminopropane.
Item Description:Gesehen am 11.12.2017
Physical Description:Online Resource
ISSN:1520-6904
DOI:10.1021/jo400576y

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