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Detection of amines with extended distyrylbenzenes by strip assays

We herein describe the synthesis and property evaluation of three novel aldehyde-substituted pentameric phenylenevinylenes carrying branched oligo(ethylene glycol) (swallowtail, Sw) substituents. The targets were synthesized by a combination of Heck coupling and Wittig or Horner reactions of suitabl...

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Bibliographic Details
Main Authors: Kumpf, Jan (Author) , Freudenberg, Jan (Author) , Fletcher, Katharyn M. (Author) , Dreuw, Andreas (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: June 17, 2014
In: The journal of organic chemistry
Year: 2014, Volume: 79, Issue: 14, Pages: 6634-6645
ISSN:1520-6904
DOI:10.1021/jo501129d
Online Access:Verlag, Volltext: http://dx.doi.org/10.1021/jo501129d
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Author Notes:Jan Kumpf, Jan Freudenberg, Katharyn Fletcher, Andreas Dreuw, and Uwe H. F. Bunz
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Summary:We herein describe the synthesis and property evaluation of three novel aldehyde-substituted pentameric phenylenevinylenes carrying branched oligo(ethylene glycol) (swallowtail, Sw) substituents. The targets were synthesized by a combination of Heck coupling and Wittig or Horner reactions of suitable precursor modules. If the pentameric phenylenevinylene carries only two of these Sw substituents, it is no longer water-soluble. When six of the Sw substituents are attached, regardless of their position, the pentameric phenylenevinylenes are well water-soluble. The dialdehydes were investigated with respect to their amine-sensing capabilities both in water as well as in the solid state, sprayed onto thin layer chromatography (TLC) plates (alox, silica gel, reversed phase silica gel). The recognition of amine vapors using the sprayed-on phenylenevinylene dialdehydes is superb and allows the identification of different amines on regular silica TLC plates via color changes, analyzed by a statistical tool, the multivariate analysis of variance (MANOVA) protocol.
Item Description:Gesehen am 11.12.2017
Physical Description:Online Resource
ISSN:1520-6904
DOI:10.1021/jo501129d

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