含硼酸之二苯乙烯胺衍生物對醣類分子之螢光感應行為之研究; Fluorescent saccharide sensors base on boron-aminostilbene

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题名:	含硼酸之二苯乙烯胺衍生物對醣類分子之螢光感應行為之研究;Fluorescent saccharide sensors base on boron-aminostilbene
作者:	李汶慧;Wen-Hui Li
贡献者:	化學研究所
关键词:	硼酸;二苯乙烯胺;aminostilbene;ICT;scaccharide
日期:	2004-08-23
上传时间:	2009-09-22 10:12:41 (UTC+8)
出版者:	國立中央大學圖書館
摘要:	中文摘要我們利用分子內電子轉移(ICT)原理設計一系列以反式二苯乙烯胺為發光團，而硼酸為感應元的化合物1C-4C作為螢光醣類分子感應器，希望藉由其與醣類分子鍵結前後之螢光的變化來探討其對醣類分子的感應行為。在緩衝水溶液的條件下，化合物1C在加入醣類分子後，其螢光呈現下降的現象，但化合物2C-4C的螢光則呈現上升的現象。化合物2C-4C在pH = 9時對D-果醣感應最好，螢光增強的幅度為2.6~4倍。在乙腈溶液中，由於醣類分子在有機溶液中的溶解度很差，因此將感應的對象改為兒茶酚或順式-1,2-環己二醇。結果發現只有化合物3C的螢光因感應而上升，而化合物1C、2C和4C的螢光皆呈現下降乙腈溶液中與緩衝溶液中的感應行為不同，顯示溶劑對化合物1C-4C的感應行為有極大的影響。 Abstract We have designed a series of new ICT-based fluorescent saccharide sensors 1C-4C, in which the aminostilbene is the fluorophore and the boronic acid group acts as the receptor. The interactions between 1C-4C and saccharides and the resulting fluorescence changes are what we would like to investigate. In buffered aqueous solution, the fluorescence of compound 1C decreases, but it is increased for compounds 2C-4C in response to the presence of D-fructose. The maximum fluorescence enhancement for 2C-4C is 2.6-4.0 fold under the condition of pH = 9. In acetonitrile, the poor solubility of saccharides prevents us from a direct study of 1C-4C-saccharide interactions. As a result, the interactions between 1C-4C and catechol or cis-1,2,-cyclohexanediol were investigated. Such interactions have led to an enhancement of fluorescence in the case of 3C, but a reduction of fluorescence for the other three species. The difference in fluorescence response in aqueous vs acetonitrile indicates that solvents play an important role in determining the fluorescence behavior of 1C-4C and their adducts with diol molecules.
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