Syntheses, Self-assembly and Metal Sensing of 1,4-Bistriazolyl-bridged Ureido Derivatives and Synthesis of Ureido Biscalix[4]arene

• Main Authors: Yang, Cheng-Jhang, 楊承璋
• Other Authors: Chung, Wen-Sheng
• Format: Others
• Language: zh-TW
• Published: 2018
• Online Access: http://ndltd.ncl.edu.tw/handle/dc6ug2

碩士 === 國立交通大學 === 應用化學系碩博士班 === 107 === In this thesis, we successfully design and synthesize a series of 1,4-bistriazoles bridged ureido derivative 38、39 and 40 by click reaction. We hoped that the hydrogen bonding interactions between the urea groups could enhance the gelation property. According to the results, we found compound 38a can form a gel in the alcohol with critical gelation concentration at 1.25 w/v %. We used variable-temperature 1H-NMR and infrared spectroscopy to gain insight into the mechanisms for self-assembly ability of urea-based compound. In addition, we observed the morphology of the gelator by SEM. Then, we added 20 different metal ions to the gel that we found Ag+ and Cu2+ caused the gel destruction. We also observed the change of absorbance to UV-Vis spectroscopy and proved binding ratio to 1:1.In the end, based on the infrared spectrum, the urea group and the ether glycol bridged group were involved in the metal ion binding.   Except for synthesizing 1,4-Bistriazolyl-bridged Ureido Derivatives and establishing a synthetic strategy for modifing the upper rim of the urea-based calix[4]arene 25, then changing for three different bridged groups via click reaction in order to synthesize the bis-uriedocalix[4]arene 41a that we get an unexpected compound 42a. Furthermore, comparing the result from other members of the group, we found the lower rim modified tri-propyl calix[4]arene 21 under the progress of 1,3-dipolar cycloaddition reaction to get compound 47. Then, we guess the lower rim modified tri-propyl functional group affect the progress for the reason. Therefore, the synthesis of the bis-uriedocalix[4]arene is still difficult, it will be needed different bridged groups or synthetic strategies to achieve the goal.