Synthesis, Photoelectrochemical and Aggregation Properties of Two New 8-hydroxyquinoline Derivatives

Two new 8-hydroxyquinoline (8-HQ) derivatives, namely 5-((4-chlorobenzene) diazene) -8-hydroxyquinoline (N-HQ) and 5-((4-chlorobenzene) methylene amino) -8-hydroxyquinoline (C-HQ), were designed and synthesized. Their structures were characterized by 1H NMR, 13C NMR, FT-IR and HR-MS. Their physical and photoelectrochemical properties were studied by absorption, emission, electrochemistry and thermog ravimetry. In addition, the gaussian program was used to calculate the geometric configurations of the two derivatives. Since N-HQ has an approximate planar configuration, it is packed in a highly ordered molecule packing in the solid state. However, there is a transverse offset between adjacent C-HQ molecules. The results show that the subtle difference of molecular structure can have a great influence on the properties of 8-HQ derivatives. This study also explored the application potential of C-HQ in fluorine ion fluorescence detection.