Multistimuli-responsive diaryldibenzofulvene derivatives and fluorescent detection of volatile organic vapors

Through molecule design, the aromatic fused ring groups (naphthyl and anthracyl) were introduced into 9-benzylidene-9H-fluorene to prepare the diaryldibenzofulvene derivatives with asymmetric structures, which exhibited typical aggregation induced emission (AIE) behavior. To multiple stimuli such as grinding, solvent fuming, and heating, the anthracene-based compound (9-(anthracen-9-yl(phenyl)methylene)-9H-fluorene) powders displayed high contrast fluorescence response behavior, whose emission could convert among yellow (570 nm), yellow green (560 nm), green (526 nm), and cyan (478 nm). Meanwhile, four single crystals of the anthracene-based compound were obtained from different conditions, exhibiting polymorphism phenomena. Through the XRD patterns and the data of the monocrystalline analysis, the different fluorescent emissions originated from changes in the molecular packing. Based on this, two fluorescent detection papers (A) and (B) were prepared using the anthracene-based compound in different solvents. The detection paper showed significant fluorescence quenching for THF and obvious fluorescence enhancement for aromatic solvents. Based on changes in fluorescence intensity and emission wavelength, various volatile organic vapors could be detected accurately by using both detection papers simultaneously. Therefore, this multi stimulus responsive fluorescent compound has potential applications in detection, recognition, sensing and other fields.