Synthesis and Properites of C3-symmetric Truxene-Based Derivates and Their Application in Supramolecular Chemistry

• Main Authors: Chia-Hui Hsu, 徐佳慧
• Other Authors: Ken-Tsung Wong
• Format: Others
• Language: zh-TW
• Published: 2012
• Online Access: http://ndltd.ncl.edu.tw/handle/40910775741093405794

碩士 === 國立臺灣大學 === 化學研究所 === 100 === In our previous studies, we developed an unique 3D skeleton based on truxene moiety. With incorporating various functional structures onto C5, C10, and C15 position of the truxene core, the successful synthetical strategy giving intriguing molecules through orthogonally and distinguishably modify active sites provides us an efficient way to further inspect on the diversity of its 3D derivatives. As a result, via involving the 3D truxene core, the thesis extend the applications of these various derivatives in supramolecular chemistry. Herein, we synthesized newly 3D organic gelator TDMDA which constructed by amide groups with long hydrocarbon chains. The morphology of TDMDA was found in fibrillar and globular morphology when dissolved in cyclohexane and methanol respectively and are characterized by SEM and TEM for close view. Moreover, gelator TDMDA incorporating amphipathic groups whose self-assembly display in-situ reversible transformation of aggregate morphology between fibrillar and globular upon exposure to different solvent. On the other hand, we also develope halide anion receptors TPTB and TDMTB from click chemistry. Accroding to NMR titration experiment, we found both of them have the best affinity to chloride due to the proper size of inner cavity. At last, we functionalized pyrene moiety onto the 3D architecture to achieve TPTHP and TDMTHP as C60 receptors, expecting it has good affinity with C60 via donor-acceptor and π-π interaction.