Summary: | 碩士 === 東海大學 === 化學系 === 100 === In part one, a number of coumarin/phenanthridine-fused heterocycles were efficiently synthesized using base-mediated annulation of coumarin and N-alkylquinolinium iodide as a key step. The prepared compounds and their corresponding ring open forms exhibit lockable switching properties, that is, they are interchangeable via pH control and can also be further converted to their “pH-inert” forms by chemical oxidation and reduction.
In part two, two new pyranocoumarins were synthesized and characterized via one-pot, microwave-assisted pseudo multicomponent condensations of coumarin and 4-methylquinoline to investigate their molecular switching properties. In addition to exhibiting acidichromism, both compound were found to be light-sensitive and have a distinct change of color upon UV irradiation. The reaction can be reverted by treating the photogenerated products with imidazoline-functionalized magnetic nanoparticles, which can be swiftly recycled with an external permanent magnet.
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