A Macrocycle – Molecular Clip Complex that Functions as a Quadruply Controllable Molecular Switch

• Main Authors: Pinn-Tsong Chiang, 江品璁
• Other Authors: 邱勝賢
• Format: Others
• Language: zh-TW
• Published: 2005
• Online Access: http://ndltd.ncl.edu.tw/handle/21517239176623868916

碩士 === 國立臺灣大學 === 化學研究所 === 93 === Herein, we synthesized a TTF contained molecular clip 1a. Under acidic condition, the known molecular clip 2 underwent a condensation reaction with 2-thioxo-1,3-dithiole. The resulting product 3 was then modified on the phenolic groups with triethylene glycol monomethyl ether tosylate to get molecular clip 5a. 5a was treated with Hg(OAc)2 to convert thione into ketone (6a). Then the resulting molecular clip 6a was reacted with 1,3-dithiole-2-thione in presence of P(OEt)3 to afford 1a. We found such TTF contained molecular clip that forms a macrocycle – molecular clip complex with a electronic complementary macrocycle. Four different sets of external stimuli – the K+/[2,2,2]cryptand, NH4+/Et3N, (p-PhBr)3NSbCl6/Zn pairs and heating/cooling cycles – allow the movement of this molecular switch to be controlled between its threaded and unthreaded states. The macrocycle – molecular clip complex not only considered as a quadruply controllable molecular switch but also can be operated by three of these stimuli as a three-input molecular NOR-functioning logic gate that may be monitored by UV-Vis spectroscopy.