Spiropyran Based Recognitions of Amines: UV-Vis Spectra and Mechanisms

As one of the important photochromic molecules, spiropyran (SP) compounds are widely used as detectors and fluorescence probes in the environment and bio-imaging field. Although great achievements have been attained for various sophisticated spiropyrans in metal ion sensing, less success is achieved in sensing organic molecules due to the weak interaction between the spiropyran and the target of the organic molecule. In this study, a spiropyran derivative containing a hydroxyl group (SPOH) was employed for the recognition of four kinds of amines via ultraviolet-visible (UV-Vis) spectra. The aliphatic primary amines, aromatic primary amines, aliphatic secondary and tertiary amines, aromatic secondary and tertiary amines were successfully distinguished according to the shapes and trends of their UV-Vis absorption spectra. The chemical reaction between aliphatic, aromatic primary amines and SPOH as well as alkalinity are two vital interaction mechanisms for the recognition process which are testified by Fourier Transform Infrared (FTIR) and Nuclear Magnetic Resonance (NMR). Although SP is generally water-insoluble, it is easy to achieve soluble by fixing SPOH inside micelle or vesicle and thus the results in this study is meaningful for amine recognition utility in environments and biological systems.