新型查尔酮荧光探针的合成及F~-的识别
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摘要
通过羟醛缩合反应合成了一种新的苯并吡喃和苯酚结构的查尔酮荧光探针C,其结构用~1H NMR,~(13)C NMR和元素分析的手段进行了表征确认.利用荧光光谱法研究了探针C在CH_3CH_2OH/H_2O的混合溶液中对不同阴离子的荧光行为.结果表明探针C对氟离子具有优异的选择性和灵敏度,与氟离子形成的氢键显示了明显的荧光响应.Job’s Plot曲线表明,探针C与F~-的配位比是1∶1.最低检测限可达2.64×10~(-5) mol/L.
A new chalcone-based fluorescent probe with chromene and phenol structure was synthesized by means of aldol condensational reaction and its structure was characterized and confirmed by means of ~1H NMR, ~(13)C NMR, and element analysis. The fluorescent respond behavior of the probe C to various anions in CH_3CH_2OH/H_2O mixed solution was investigated with fluorescence spectroscopy. The experimental result showed that the probe C would have excellent selectivity for and sensitivity to fluoride ions. The hydrogen bonding formed with fluoride anion would show remarkable fluorescent response. The coordinative ratio of probe C to F~- would be 1∶1 according to Job's Plot method and the detection limit of F~- would be 2.64×10~(-5 ) mol/L.
A new chalcone-based fluorescent probe with chromene and phenol structure was synthesized by means of aldol condensational reaction and its structure was characterized and confirmed by means of ~1H NMR, ~(13)C NMR, and element analysis. The fluorescent respond behavior of the probe C to various anions in CH_3CH_2OH/H_2O mixed solution was investigated with fluorescence spectroscopy. The experimental result showed that the probe C would have excellent selectivity for and sensitivity to fluoride ions. The hydrogen bonding formed with fluoride anion would show remarkable fluorescent response. The coordinative ratio of probe C to F~- would be 1∶1 according to Job's Plot method and the detection limit of F~- would be 2.64×10~(-5 ) mol/L.
引文
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[3] LIU Y,WANG S Q,ZHAO B X.A novel pyrazoline-based fluorescent probe for detecting fluoride ion in water and its application on real samples [J].RSC Advances,2015,5:32962-32966.
[4] 曾晓丹,朱宝存,朱琳.H2O2荧光探针与人血清白蛋白相互作用的研究 [J].应用化工,2017,46(8):1640-1643.
[5] 曾丽,赵江林,牟兰,等.一种同时分辨识别Zn2+和F-离子的双功能探针 [J].无机化学学报,2017,33(5):769-778.
[6] 苏策,王鹏.可识别 Al3+的香豆素类荧光增强型探针的合成及性能 [J].兰州理工大学学报,2018,44(1):65-69.
[7] 徐栋,王鸣明,曾瑞杰,等.双席夫碱荧光探针的合成及金属离子的选择性识别 [J].应用化工,2013,42(9):1712-1715.
[8] HRISHIKESAN E,KANNAN P.Azobenzene chemosensor based on nitrogen chelator for the detection of Cu(II) ion in aqueous medium [J].Inorganic Chemistry Communications,2013,37:21-25.
[9] ZHANG Y M,LIN Q,WEI T B,et al.Simple colorimetric sensors with high selectivity for acetate and chloride in aqueous solution [J].Sensors and Actuators B:Chemical,2009,137(2):447-455.
[10] DUKE R M,VEALE E B,PFEFFER F M,et al.Colorimetric and fluorescent anion sensors:an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors [J].Chemical Society Reviews,2010,39(10):3936-3953.
[11] PIATEK P,JURCZAK J.A selective colorimetric anion sensor based on an amide group containing macrocycle [J].Chemical Communications,2002(20):2450-2451.
[12] WU J,LIU W,GE J,et al.New sensing mechanisms for design of fluorescent chemosensors emerging in recent years [J].Chemical Society Reviews,2011,40(7):3483-3495.
[13] 李欠.含有酚羟基的吖嗪类荧光探针的阴离子识别与传感研究 [J].化学教育,2017,38(18):39-43.
[14] BHOSALE S V,BHOSALE S V,KALYANKAR M B,et al.A core-substituted naphthalene diimide fluoride sensor [J].Organic Letters,2009,11:5418-5421.
[15] NAYAK S,CHAKROBORTY S,BHAKTA S,et al.Design and synthesis of(E)-4-(2-Phenyl-2H-chromen-3- yl) but-3-en-2-ones and evaluation of their in vitro antimicrobial activity [J].Letters in Organic Chemistry,2015,12(5):352-358.
[16] FIROOZPOUR L,EDRAKI N,NAKHJIRI M,et al.Cytotoxic activity evaluation and QSAR study of chromene-based chalcones [J].Archives of Pharmacal Research,2012,35(12):2117-2125.
[17] ZHOU Y,ZHANG J F,YOON J.Fluorescence and colorimetric chemosensors for fluoride-ion detection [J].Chemical Reviews,2014,114(10):5511-5571.
[18] 刘阁,曹洪玉,邵杰.新型含酚羟基Schiff碱化合物的比色阴离子传感器 [J].有机化学,2011,31(10):1678-1682.
[19] 吴芳英,谭晓芳,胡美华,等.喹啉类主体分子的设计合成与阴离子识别 [J].化学学报,2004,62(15):1451-1454.