Supramolecular self-assembly system based on naphthalimide boric acid ester derivative for detection of organic amine

摘要

Graphical abstractDisplay OmittedHighlights•N12andN18can emit strong blue light in solution and gel states.•This gelator in solution and gel states all can respond to different organic amine with the fluorescence emission quenching.•The study demonstrated a novel approach for developing organic amine sensors.AbstractTwo new gelators (N12andN18) containing naphthalimides group were designed and synthesized which the C-4 of naphthalimide derivative was modified by isopropoxyboronic acid ester. The two gelators could form gels in different solvents, and different structures were formed and exhibited hydrophobicity. The self-assembly processes of gelator were investigated by UV–vis, fluorescence, infrared spectroscopy, field emission scanning electron microscope (FE-SEM), X-ray diffraction, NMR spectrum and contact angle experiments in detail. The gelator in solution or gel state could emit blue light which response to some organic amine, and the fluorescence of gelator was quenched. The fluorescence of gelator could be recovered after acid was added again. Take Et3N for instance, the association constant (K) betweenN12and Et3N was calculated to be 3.75×103M−1and the gelatorN12could detect Et3N in solution with the detection limit of 4.77×10−7M. This research would expand the supramolecular self-assembly materials application in sensor field and offer a new detection method for organic amines.