A 1,3-indandione-functionalized tetraphenylethene: aggregation-induced emission, solvatochromism, mechanochromism, and potential application as a multiresponsive fluorescent probe

Abstract

A tetraphenylethene (TPE) derivative substituted with the electron-acceptor 1,3-indandione (IND) group was designed and prepared. The targeted IND-TPE reserves the intrinsic aggregation-induced emission (AIE) property of the TPE moiety. Meanwhile, owing to the decorated IND moiety, IND-TPE demonstrates intramolecular charge-transfer process and pronounced solvatochromic behavior. When the solvent is changed from apolar toluene to highly polar acetonitrile, the emission peak redshifts from 543 to 597 nm. IND-TPE solid samples show an evident mechanochromic process. Grinding of the as-prepared powder sample induces a redshift of emission from green (peak at 515 nm) to orange (peak at 570 nm). The mechanochromic process is reversible in multiple grinding-thermal annealing and grinding-solvent-fuming cycles, and the emission of the solid sample switches between orange (ground) and yellow (thermal/solvent-fuming-treated) colors. The mechanochromism is ascribed to the phase transition between amorphous and crystalline states. IND-TPE undergoes a hydrolysis reaction in basic aqueous solution, thus the red-orange emission can be quenched by OH(-) or other species that can induce the generation of sufficient OH(-). Accordingly, IND-TPE has been used to discriminatively detect arginine and lysine from other amino acids, due to their basic nature. The experimental data are satisfactory. Moreover, the hydrolyzation product of IND-TPE is weakly emissive in the resultant mixture but becomes highly blue-emissive after the illumination for a period by UV light. Thus IND-TPE can be used as a dual-responsive fluorescent probe, which may extend the application of TPE-based molecular probes in chemical and biological categories.

Keywords: UV/Vis spectroscopy; fluorescence; fluorescent probes; mechanochromism; solvatochromism.