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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| Hauptverfasser: | , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
April 15, 2013
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| In: |
The journal of organic chemistry
Year: 2013, Jahrgang: 78, Heft: 10, Pages: 4949-4959 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/jo400576y |
| Online-Zugang: | Verlag, Volltext: http://dx.doi.org/10.1021/jo400576y
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| Verfasserangaben: | Jan Freudenberg, Jan Kumpf, Vera Schäfer, Eric Sauter, Svenja J. Wörner, Kerstin Brödner, Andreas Dreuw, and Uwe H. F. Bunz |
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| 520 | |a 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. | ||
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