Water-soluble fluorescent boronic acid compounds for saccharide sensing: substituent effects on their fluorescence properties.
Water-soluble fluorescent boronic acid compounds for saccharide sensing: substituent effects on their fluorescence properties.
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DOI：
10.1002/chem.200500982
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发表时间：
2006-02
期刊：
影响因子：
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通讯作者：
Yanling Zhang;Xingming Gao;K. Hardcastle;B. Wang
中科院分区：
文献类型：
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作者：
Yanling Zhang;Xingming Gao;K. Hardcastle;B. Wang
合成了四种新的萘基硼酸化合物（1-4）。在pH为7.4的磷酸盐缓冲液中研究了不同碳水化合物对其荧光性质的影响。萘环上苯胺基的不同取代导致这四种化合物的荧光性质有显著差异。化合物1在加入糖后表现出比例荧光变化。化合物2和3不显示比例荧光变化，但显示非常大的荧光强度变化（荧光强度增加约70倍）。加入糖后，除了可量化的荧光性质变化外，1-3的荧光颜色变化也是肉眼可见的。然而，苯胺氮原子的酰胺化显著降低了化合物4的荧光强度。一种硼酸的晶体结构为这些化合物的荧光特性提供了一些重要的结构特征。
Four new naphthalene-based boronic acid compounds (1-4) were synthesized. The effect of various carbohydrates on their fluorescence properties has been studied in aqueous phosphate buffer at pH 7.4. Different substitutions on the aniline group of the naphthalene ring resulted in significant differences in fluorescence properties for these four compounds. Compound 1 shows ratiometric fluorescence changes upon addition of a sugar. Compounds 2 and 3 do not show ratiometric fluorescence changes but show very large fluorescence intensity changes (about 70-fold fluorescence intensity increase). In addition to the quantifiable fluorescence property changes upon sugar addition, the fluorescence color changes of 1-3 are also visible to the naked eye. However, amidation of the aniline nitrogen atom significantly diminishes the fluorescence intensity of compound 4. The crystal structure of one boronic acid provided some insight into the structural features that are important for the fluorescence properties of these compounds.