ANION-BINDING AND SENSING PROPERTIES OF NOVEL RECEPTORS BASED ON N-(INDOL-3-YLGLYOXYLYL)BENZYLAMINE

• Main Authors: Wei Wei, Yong jun Lv, Shi jun Shao, Yong Guo
• Format: Article
• Language: English
• Published: Sociedade Brasileira de Química 2015-12-01
• Series: Química Nova
• Subjects: anion recognition; indoly benzylamine; hydrogen bonds; spectroscopy
• Online Access: http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422015001001293&lng=en&tlng=en

Indole-based receptors such as biindole, carbazole, and indolocarbazole are regarded as some of the most favorable anion receptors in molecular recognition. This is because indole groups possess N–H groups as hydrogen-bonding donors. The introduction of amide groups in the indole framework can induce strong binding properties and good water solubility. In this study, we designed and synthesized a series of N-(indol-3-ylglyoxylyl)benzylamine derivatives as novel and simple anion receptors. The receptors derived by aryl and aliphatic amines can selectively recognize F– based on a color change from colorless-to-yellow in DMSO. The receptors derived by hydrazine hydrate can recognize F–, AcO–, and H2PO4– by similar color changes in DMSO and can even enable the selective recognition of F– in a DMSO–H2O binary solution by the naked eye. Spectrographic data indicate that complexes are formed between receptors and anions through multiple hydrogen-bonding interactions in dual solutions.