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第 1 期                     宋   健,等:  基于咖啡酸的水合肼荧光探针的合成及应用                                   ·55·


            2.7    应用研究                                        3   结论
                 为了研究探针在实际生活中的应用,将直径为
            4 cm 的圆形滤纸放在 10  μmol/L 的探针溶液中浸泡                       以资源丰富的天然提取物咖啡酸为原料,设计
            2 min 后取出,自然风干后拍照如图 8 所示。可以看                       合成了一种基于咖啡酰基结构的新型小分子荧光探
            出,随着N 2H 4 浓度(70、100、150、300、450、600 μmol/L)       针 ED,探针 ED 可用于特异性识别 N 2 H 4 。荧光探
            的增加,负载 ED 的滤纸的荧光颜色逐渐由蓝色变为                          针具有合成简单、响应时间短(48 s)、选择性高、
            蓝绿色,该试纸可用于水样中微量 N 2H 4 的检测,为                       检测限低(0.31 μmol/L)、pH 适用范围宽(pH 3~8)
                                                                                     13
            N 2H 4 的便捷、快速检测提供了新的方法。                            等特点。通过 HNMR、 CNMR 和 HRMS 对探针
                                                                            1
                 随后,将化合物ED用于环境水样中N 2H 4 的检测,                   结构进行表征,探索探针 ED 对 N 2 H 4 的识别机理。
            结果如图 9 所示。可以看出,在 493 nm 处,3 种水样                    应用研究表明,基于探针 ED 的试纸可用于水样中
            溶液的荧光强度与 N 2H 4 浓度(15、20、25、30、35、                 N 2 H 4 的痕迹检测。咖啡酰基有机荧光探针的合成,
                                        2
            40 μmol/L)均呈线性关系,且 R 值均>0.99。如表 1                  不仅拓宽了天然提取物咖啡酸在荧光材料领域的应
            所示,3 种水样的回收率均在 95.2%~104.9%之间,回
                                                               用,而且为咖啡酸的深度加工利用提供了重要的理
            收率较高,表明化合物 ED 可用于实际水样中 N 2H 4                      论依据。
            的痕量检测。

                                                               参考文献:
                                                               [1]   XIA X T, ZENG F, ZHANG P S,  et al. An ICT-based ratiometric
                                                                   fluorescent probe for hydrazine detection and its application in living
                                                                   cells and in vivo[J]. Sensors and Actuators B: Chemical, 2016, 227:
                                                                   411-418.

            图 8   在 365 nm 紫外灯下,用不同浓度 N 2 H 4 处理探针             [2]   WANG X C, DING G, HUANG C H, et al. A novel triphenylamine-
                                                                   based bis-Schiff  bases fluorophores with  AIE activity as the
                  ED 涂层滤纸的照片
            Fig.  8    Photos of  probe ED coated filter  paper treated  with   hydrazine fluorescence turn-off probes and  cell imaging in live
                                                                   cells[J]. Talanta, 2020, 217: 121029-121040.
                   different concentrations of N 2 H 4  under 365 nm UV lamp   [3]   DING Y, ZHAO S, WANG Q,  et al. Construction of a coumarin

                                                                   based fluorescent  sensing  platform for palladium and  hydrazine
                                                                   detection[J]. Sensors and Actuators B: Chemical, 2018, 256: 1107-1113.
                                                               [4]   CHEN Z,  ZHONG X X,  WANG  B,  et al.  A highly selective
                                                                   HBT-based "turn-on" fluorescent probe for hydrazine detection and
                                                                   its application[J]. Tetrahedron Letters, 2017, 58: 2596-2601.
                                                               [5]   LIU Y, REN D, YANG X F, et al. A fluorescent probe for hydrazine
                                                                   based on a newly developed 1-indanonefused coumarin scaffold[J].
                                                                   Dyes and Pigments, 2019, 162: 112-119.
                                                               [6]   ALI F, ANILA H A, TAYE N, et al. Specific receptor for hydrazine:
                                                                   Mapping the in situ release of hydrazine in live cells and in an in
                                                                   vitro enzymatic assay[J]. Chemical Communications, 2016, 52(36):
                                                                   6166-6169.
                                                               [7]   GARROD  S, BOLLARD  M E, HOLMES  E,  et al. Integrated

                                                                   metabonomic analysis of the multiorgan effects of hydrazine toxicity
            图 9   在实际水样中探针 ED(10 μmol/L)的荧光强度随                     in the rat[J]. Chemical Research in Toxicology, 2005, 18: 115-122.
                  N 2 H 4 浓度的变化                                [8]   LUO Z, LIU  B, QIN  T,  et al. Cyclization of chalcone enables
            Fig. 9    Changes of fluorescence intensity of probe ED   ratiometric fluorescence determination of  hydrazine with a high
                   (10 μmol/L) with N 2 H 4  concentration in an actual   selectivity[J]. Sensors and Actuators B: Chemical, 2018, 263: 229-236.
                   water samples                               [9]   TENG M G, ZHOU Z X, CAO J X, et al. A water-soluble fluorescence
                                                                   sensor with high specificity for detecting hydrazine in river water
                       表 1   不同水样中 N 2 H 4 的测定                     detection and  A549 cell imaging[J]. Sensors and  Actuators B:
             Table 1    Determination of N 2 H 4  in different water samples   Chemical, 2020, 311: 127914-127921.
                                                               [10]  CUI L, JI C F, PENG Z X, et al. Unique tri-output optical probe for
                      添加 N 2H 4 浓度/   检测到 N 2H 4 浓度/
               样品                                 回收率/%            specific  and ultrasensitive  detection of hydrazine[J]. Analytical
                        (μmol/L)      (μmol/L)
                                                                   Chemistry, 2014, 86(9): 4611-4617.
              蒸馏水         15            15.34       102.3      [11]  LI L, LIANG X,  XU Y,  et al. Doxorubicin and indocyanine green
                          18            17.31        96.2          loaded hybrid bicelles for fluorescence imaging guided synergetic
                          20            19.04        95.2          chemo/photothermal therapy[J]. Bioconjugate Chemistry, 2017,
                          25            25.13       100.5          28(9): 2410-2419.
              矿泉水         15            14.84        98.9      [12]  GU L, ZHENG T, XU Z X, et al. A novel bifunctional fluorescent
                          18            18.89       104.9          and colorimetric probe for detection of mercury and fluoride ions[J].
                                                                   Spectrochimica Acta, Part A: Molecular and Biomolecular
                          20            19.93        99.7
                                                                   Spectroscopy, 2018, 207: 88-95.
                          25            25.41       101.6      [13]  LENG T, MA Y, CHEN G, et al. A novel ratiometric fluorescence and
              自来水         15            14.78        98.5          colorimetric probe with a large stokes shift for Hg  sensing[J].
                                                                                                    2+
                          18            18.21       101.2          Journal of Photochemistry and Photobiology A: Chemistry, 2018,
                          20            20.18       100.9          353: 143-149.
                          25            26.06       104.2                                      (下转第 62 页)
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