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大连理工大学化学系 精细化工国家重点实验室,辽宁 大连,116024
收稿日期:2011-03-11,
修回日期:2011-04-25,
网络出版日期:2011-09-22,
纸质出版日期:2011-09-22
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张亚男, 杨林林, 周硼, 段春迎. 磷酸二氢根离子对香豆肼化合物的高选择性荧光增强[J]. 发光学报, 2011,32(9): 962-967
ZHANG Ya-nan, YANG Lin-lin, ZHOU Peng, DUAN Chun-ying. Fluorescent Emission of Coumaric Aldehyde Molecule Enhanced by Dihydrogen Phosphate[J]. Chinese Journal of Luminescence, 2011,32(9): 962-967
设计合成了荧光探针N
N-二乙基氨基香豆素-3-肼基-2
4-二硝基苯肼(DC)。光谱滴定实验显示
H
2
PO
4
-
与DC能够以1: 1的化学计量比形成配合物。进一步的实验发现
和相同含量的DC溶液相比
该配合物溶液的相对光致荧光强度显著增强
同时伴有紫外吸收光谱红移
溶液颜色由橙黄色迅速变为紫色。其它阴离子
如 F
-
、NO
3
-
、Cl
-
、Br
-
、I
-
等对DC 溶液的相对荧光强度及紫外吸收光谱没有影响。利用DC对H
2
PO
4
-
具有灵敏选择性的特征
可把N
N-二乙基氨基香豆素-3-肼基-2
4-二硝基苯肼作为荧光探针
借助于荧光光谱和紫外-可见吸收光谱两种手段
实现对H
2
PO
4
-
离子的快速识别。
By combining 7-diethylamino-2-oxo-2H-chromene-3-carbohydrazide with 2
4-dinitrophenylhydrazine into one molecule
fluorescent probe (DC) was synthesized for dsetection of H
2
PO
4
-
in acetonitrile. Spectrophotometric titration indicated the formation of a 1:1 complex of H
2
PO
4
-
with DC. With the fluorescence spectra
the apparent red shift of UV absorption and the changes for the solution color from orange yellow to purple were observed as binding DC with H
2
PO
4
-
. The experiment showed that DC was highly selective for H
2
PO
4
-
much more than those anions such as F
-
NO
3
-
Cl
-
Br
-
and I
-
. By the exclusive selectivity of DC to H
2
PO
4
-
it was predicted that as a fluorescent probe
and by means of fluorescence and UV-Visible absorption spectrum
H
2
PO
4
-
can be rapidly identified by a enhanced fluorescence from DC.
Kang S O, Begum R A, Bowman-James K. Amide-based ligands for anion coordination [J]. Angew. Chem. Int. Ed., 2006, 45 (47):7882-7894.[2] Beer P D, Gale P A. Anion recognition and sensing: The state of the art and future perspectives [J]. Angew. Chem. Int. Ed., 2001, 40 (3):486-516.[3] Sung O K, Jose'M L, Douglas l, et al. New polyamide cryptand for anion binding [J]. J. Am. Chem. Soc., 2003, 125 (3-4):10152-10153.[4] Suksai C, Untulani T. Chromogenic anion sensors [J]. Chem. Soc. Rev., 2003, 32 (4):192-202.[5] Choi K, Hamilton A D. Selective anion binding by a macrocycle with convergent hydrogen bonding functionality [J]. J. Am. Chem. Soc., 2001, 123 (10):2456-2457.[6] Ma Yongshan, Zhang Fengxia, Zhang Youmin, et al. Synthesis and characterization of a pH fluorescence probe based on water soluble perylene diimide derit [J]. Chin. J. Lumin. (发光学报), 2011, 32 (3):251-255 (in Chinese).[7] Wu Hongmei, He Cheng, Wang Jian, et al. Hydrolysis-activated fluorophore system as a molecular sensor for selective detection of Zn2+ [J]. Chin. J. Lumin. (发光学报), 2009, 30 (3):275-283 (in English).[8] Vzquez M, Fabbrizzi L, Taglietti A, et al. A colorimetric approach to anion sensing: A selective chemosensor of fluoride ions, in which color is generated by anion-enhanced delocalization [J]. Angew. Chem. Int. Ed., 2004, 43 (15):1962-1965.[9] Fu Meiyan, Xiao Yi. The synthesis and application of a new thiocyanate sensor based on naphthalimide [J]. Chin. J. Lumin. (发光学报), 2009, 30 (4):482-486 (in Chinese).[10] Liu Baosheng, Xue Chunli, Wang Jing, et al. Studies on the interaction between ciprofloxacin and ofloxacin in presence of bovine serum albumin by spectroscopic methods [J]. Chin. J. Lumin. (发光学报), 2009, 31 (2):285-290 (in Chinese).[11] Peng Xiaojun, Wu Yunkou, Fan Jiangli, et al. Colorimetric and ratiometric fluorescence sensing of fluoride:tuning selectivity in proton transfer [J]. J. Org. Chem., 2005, 70 (25):10524-10531.[12] Lin Zhihua, Ou Shengju, Duan Chunying, et al. Naked-eye detection of fluoride ion in water: An remarkably selective easy-to-prepare test paper [J]. Chem. Commun., 2006(6):624-626.[13] Lin Zhihua, Zhao Yonggang, Duan Chunying, et al. A highly selective chromo- and fluorogenic dual responding fluoride sensor: naked-eye detection of F- ion in natural water via a test paper [J]. Dalton Trans., 2006(30):3678-3684.[14] Gale P A. Synthetic indole, carbazole, biindole and indolocarbazole-based receptors: applications in anion complexation and sensing [J]. Chem. Commun., 2008(38):4525-4540.[15] Hu Rui, Feng Jiao, Hu Dehui, et al. A rapid aqueousfluoride ion sensor withdual output modes [J]. Angew. Chem. Int. Ed., 2010, 49 (29):4915-4918.[16] Zapata F, Caballero A, Tarraga A, et al. Ferrocene-substituted nitrogen-rich ring systems as multichannel molecular chemosensors for Aanions in aqueous environment [J]. J. Org. Chem., 2010, 75 (1):162-169.[17] Shiraishi Y, Sumiya S, Kohno Y, et al. A rhodamine-cyclen conjugate as a highly sensitive and selective fluorescent chmosensor for Hg(Ⅱ) [J]. J. Org. Chem., 2008, 73 (21):8571-8574.[18] Benesi H A, Hildebrand J H. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons [J]. J. Am. Chem. Soc., 1949, 71 (8):2703-2707.
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