Grind, shine and detect: mechanochemical synthesis of AIE-active polyaromatic amide and its application as molecular receptor of monovalent anions or nucleotides

Abstract

A mechanochemical synthesis of novel polyaromatic amide consisting of 1,3,5-triphenylbenzene and 1,1′,2,2′-tetraphenylethylene skeletons has been established. The designed mechanochemical approach using readily available and low-cost equipment allowed a twofold increase in reaction yield, a 350-fold reduction in reaction time and a significant reduction in the use of harmful reactants in comparison to the solution synthesis method. The parameters of Green Chemistry were used to highlight the advantages of the developed synthesis method over the solution-based approach. The title compound was found to exhibit attractive optical properties related to the Aggregation-induced emission (AIE) behaviour. Taking the advantage of AIE-active properties of the synthesized polyaromatic amide, its application as effective and versatile molecular receptor towards detection of monovalent anions, as well as bio-relevant anions – nucleotides, has been demonstrated. The values of the binding constants were at the satisfactory level of 10⁴, the detection limit values were low and ranged from 0.2 μM to 19.9 μM.