Synthesis and Recognition Behavior Studies of Indole Derivatives

• Main Authors: Yang, Jun-Chun, 楊鈞醇
• Other Authors: Lin, Mei-Ching
• Format: Others
• Language: zh-TW
• Published: 2019
• Online Access: http://ndltd.ncl.edu.tw/handle/bqbt7z

碩士 === 朝陽科技大學 === 應用化學系 === 107 === In this study, a series of chemical sensor compose with indole and benzophenone as the main structure was synthesized, also we modified the methyl and fluorine functional group on the benzene ring of benzophenone to obtain compound X, X1 and X2. Take UV-Vis spectrum and fluorescence spectrum to investigate photophysical properties of compound X, X1, and X2, also evaluate the recognition behavior of ions. In the UV-Vis spectrum, the absorption peaks of benzene rings and indole moiety were observed at 253 nm and 350 nm, however, the fluorescence was very low. When 5 mg of various metal ions and anions were added to compounds, it was found that only Cu2+ induce a new, strong emission peaks at 530 nm, 510 nm and 540 nm for compound X, X1 and X2, respectively. This phenomenon indicate that X, X1 and X2 have highly selectivity recognition behavior for Cu2+. Job's plot indict that the coordination ratio of the compound and Cu2+ were 1:1. The binding constants were more then 10-3 M-1 by titration experiment. After adding CN-, the fluorescence intensity increased slightly, which means that all the compounds were capable to recognize CN- too. X1 produces a new emission peak at 451 nm. The sensing mechanism was explored by 1H NMR and photophysical spectrum. When Cu2+ was coordinated, a new absorption peak of MLCT (Metal to ligand charge transfer) appears at 440 nm, which involved with energy release through fluorescence from the excited state. For anion recognition, CN- induce the deprotonation of indole group, and the conjugated system was affected, which is not conducive the process of PET (Photo induced electron transfer), and the probability of excited electron density was increased in indole group.