Water-soluble cruciforms and distyrylbenzenes

• Verfasst von: Freudenberg, Jan [VerfasserIn]
• Verfasst von: Kumpf, Jan [VerfasserIn]
• Verfasst von: Sauter, Eric [VerfasserIn]
• Verfasst von: Wörner, Svenja [VerfasserIn]
• Verfasst von: Brödner, Kerstin [VerfasserIn]
• Verfasst von: Dreuw, Andreas [VerfasserIn]
• Verfasst von: Bunz, Uwe H. F. [VerfasserIn]
• Titel: Water-soluble cruciforms and distyrylbenzenes
• Titelzusatz: synthesis, characterization, and pH-dependent amine-sensing properties
• Verf.angabe: Jan Freudenberg, Jan Kumpf, Vera Schäfer, Eric Sauter, Svenja J. Wörner, Kerstin Brödner, Andreas Dreuw, and Uwe H. F. Bunz
• Umfang: 11 S.
• Fussnoten: Gesehen am 11.12.2017
• Titel Quelle: Enthalten in: The journal of organic chemistry
• Jahr Quelle: 2013
• Band/Heft Quelle: 78(2013), 10, S. 4949-4959
• ISSN Quelle: 1520-6904
• DOI: doi:10.1021/jo400576y
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1566232643

Abstract

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.