一种“裸眼”可视化检测溶液的pH值及细胞中铁离子的BODIPY类探针
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摘要
以吡啶-2-甲酸(4-甲酰基苯酚)酯代替对羟基苯甲醛,将对羟基苯基引入到BODIPY染料的3-位,以高产率得到一个BODIPY类探针2。探针2易溶解到各种有机溶剂中,在甲醇溶液中的最大吸收和发射波长分别为570和585 nm,荧光量子产率达到0.9。当溶液的pH值从酸性过渡到碱性时,对羟基苯乙烯基团会慢慢失去质子,其溶液最大吸收波长发生红移,荧光发生淬灭,而且溶液颜色也发生明显的变化。因此,探针2可作为一种"裸眼"可视化的pH探针。此外,探针2对Fe~(3+)也有明显的响应,在溶液中加入Fe~(3+),探针2分子结构中乙烯基团发生断裂,其溶液最大吸收波长和最大发射峰均发生蓝移。因此,探针2也可以作为Fe~(3+)的比率型探针。同时探针2毒性较低、渗透性好、对Fe~(3+)选择性高,可以应用到细胞中检测Fe~(3+)的含量。
A fluorescence probe 2 containing 4-hydroxystyryl at the 3-position on the boron fluoride dipyrromethene(BODIPY) fluorophore was successfully synthesized in high yield using the 4-formylphenyl picolinate as the starting material instead of 4-hydroxybenzaldehyde. Probe 2 exhibits excellent optical performance, including good solubility, high extinction coefficient and high fluorescence quantum yield(Ф =0.90 in CH_3OH). The absorption and emission bands of probe 2 are centered at 570 and 585 nm in CH_3OH, respectively. When the pH value of the solution changes from acidity to basicity, both positive fluorescence response and visual color change make naked-eye detection of pH value possible due to the deprotonation of hydroxyl group. With the addition of Fe~(3+)ions into the solution, visual color changes and blue shift of the absorption and fluorescence peak were detected as well. Hence, the probe 2 could also be used as a ratiometric fluorescent probe for selectively monitoring Fe~(3+)ion in solution and in living cells.
A fluorescence probe 2 containing 4-hydroxystyryl at the 3-position on the boron fluoride dipyrromethene(BODIPY) fluorophore was successfully synthesized in high yield using the 4-formylphenyl picolinate as the starting material instead of 4-hydroxybenzaldehyde. Probe 2 exhibits excellent optical performance, including good solubility, high extinction coefficient and high fluorescence quantum yield(Ф =0.90 in CH_3OH). The absorption and emission bands of probe 2 are centered at 570 and 585 nm in CH_3OH, respectively. When the pH value of the solution changes from acidity to basicity, both positive fluorescence response and visual color change make naked-eye detection of pH value possible due to the deprotonation of hydroxyl group. With the addition of Fe~(3+)ions into the solution, visual color changes and blue shift of the absorption and fluorescence peak were detected as well. Hence, the probe 2 could also be used as a ratiometric fluorescent probe for selectively monitoring Fe~(3+)ion in solution and in living cells.
引文
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