Triptycene scaffolds: Synthesis and properties of triptycene-derived Schiff base compounds for the selective and sensitive detection of CN− and Cu2+. Issue 20 (18th May 2017)

• Record Type: Journal Article
• Authors: Emandi, Ganapathi; Browne, Michelle P.; Lyons, Michael E.; Prior, Caroline; Senge, Mathias O.
• Is Part Of: Tetrahedron. Volume 73:Issue 20(2017)
• Page Start: 2956
• Page End: 2965
• Publication Date: 2017-05-18
• Subjects: Triptycene -- Schiff base -- Sensor -- Cyanide -- Copper ions; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.04.005
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A series of triptycene-derived Schiff bases were synthesized by condensation between amino triptycenes with an appropriate aldehyde and were isolated in good to excellent (85–90%) yields. Amongst these, a triptycene-hydroxybenzaldehyde Schiff base compound proved to be a selective sensor for cyanide. It exhibited a "turn-on" fluorescence response at 490 nm to CN − facilitated by the nucleophilic addition of CN − to the aldehyde group, accompanied by a visible color change from orange to yellow. Likewise, a triptycene salicylaldehyde adduct was shown to be highly sensitive towards the detection of the CN − ion with a detection limit of 0.9 μM. On the other hand a triptycene-BODIPY Schiff base compound could be used for the detection of Cu 2+ ions over other competing, biologically relevant metal ions in acetonitrile. Photophysical studies revealed a 1:1 binding model for the triptycene-BODIPY compound. Graphical abstract: