Theoretical and Experimental: The Synthetic and Anion-Binding Properties of Tripodal Salicylaldehyde Derivatives

• Main Authors: Zhong-Jie Xu, Li-Rong Zhang
• Format: Article
• Language: English
• Published: MDPI AG 2016-05-01
• Series: Sensors
• Subjects: molecular probe; tripodal compound; theoretical investigation; colorimetric binding; nano-material
• Online Access: http://www.mdpi.com/1424-8220/16/5/733

A series of colorimetric anion probes 1–6 containing OH and NO2 groups were synthesized, and their recognition properties toward various anions were investigated by visual observation, ultraviolet–visible spectroscopy, fluorescence, 1H nuclear magnetic resonance titration spectra and theoretical investigation. Nanomaterials of three compounds 2–4 were prepared successfully. Four compounds 3–6 that contain electron-withdrawing substituents showed a high binding ability for AcO−. The host–guest complex formed through a 1:1 binding ratio, and color changes were detectable during the recognition process. Theoretical investigation analysis revealed that an intramolecular hydrogen bond existed in the structures of compounds and the roles of molecular frontier orbitals in molecular interplay. These studies suggested that this series of compounds could be used as colorimetric probes to detect of AcO−.