Tuning aggregation-induced emission properties with the number of cyano and ester groups in the same dibenzo[b,d]thiophene skeleton for effective detection of explosives

Abstract

Three aggregation-induced emission (AIE) active molecules were designed and synthesized where they have the same dibenzo[b,d]thiophene skeleton but the different number of cyano and ester groups. Aggregation-induced fluorescence experiments reveal that compounds 1–3 show a remarkable bathochromic-shift and AIE phenomenon. With the enhancement of water volume fractions, the intensity of emission band presents a step-by-step increase when fw=0–70% in compound 1, where the maximum emission wavelength is 564nm in the aggregated state and the peak area when fw=90% is 5-fold more than that when fw=0%. Furthermore, fluorescence titration results demonstate that this family of dibenzothiophene derivatives 1–3 is one of potential selective chemosensors for picric acid in aqueous phase and the obvious color change of the cellulose-based dibenzothiophene mixtures is illustrated with the addition of different explosives. In addition, theoretic computational studies on related luminogens have been carried out. To the best of our knowledge, this is the first fabrication of cellulose-based dibenzothiophene composites exhibiting AIE properties for effective detection of explosives.