Sensitive Fluorescence Detection of Phthalates by Suppressing the Intramolecular Motion of Nitrophenyl Groups in Porous Crystalline Ribbons

Abstract

A novel, highly sensitive fluorescence sensor for phthalates is developed by introducing nitrophenyl groups to a trifluorene molecule that can form porous crystalline ribbons. On the basis of single-crystalline analysis and theoretical calculations, we demonstrate that phthalate molecules can diffuse into the caves of crystalline ribbons and effectively suppress the rotation of nitrophenyl groups via noncovalent interactions to enhance the emission. Because of this novel response mechanism, fluorescence detection of phthalates with high sensitivity (the limit of detection of widely used di(2-ethylhexyl) phthalate (DEHP) is 0.03 ppb) and rapid reversible turn-on responses is achieved. Sensitive detection of phthalates released from commercial polyvinyl chloride (PVC) products further illustrate the utility of such a sensor in in situ and real-world applications.