Phenolic −OH-Induced Fluorescence and Chemoselectivity in a Triptycene-Based trans-Azo Oligomer for Sensing Applications

Abstract

A novel triptycene-based trans-azo fluorescent oligomer exhibiting phenolic groups has been designed. The presence of phenolic −OH in conjugation with the azo group rendered the oligomer fluorescence active by keto–enol tautomerism, which was evidenced by quenching the fluorescence intensity of TP1 in 1 M aq. NaOH. A green synthetic protocol was employed to synthesize this oligomer as a dark-brown solid, and it was characterized by using diverse analytical tools such as FTIR, ¹³C-CPMAS NMR, GPC, FESEM, EDS, TGA, and PXRD techniques. FESEM and PXRD confirmed its existence as amorphous nanoclusters. The oligomer displayed efficient chemosensing properties toward the detection of picric acid with the LOD value of 391 nM. The specific recognition of PA in the presence of other explosives and the results of real water sample analysis further indicated the high efficacy of the TP1 as a chemosensor.