罗丹明B衍生物荧光探针的合成及其对Fe~(3+)的检测
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摘要
以罗丹明B与苯胺为原料,经过缩合反应制得一种罗丹明B衍生物的荧光探针F-1[3',6'-二(二乙基氨基)-2-苯基螺[异吲哚-3,9'-氧杂蒽]-1-酮],其结构通过1HNMR、13CNMR、红外光谱和高分辨质谱(HRMS)进行确证。Fe~(3+)加入探针体系后,体系颜色由无色变为紫色,荧光显著增强,而不受其他金属离子(Na~+、K~+、Ca~(2+)、Mg~(2+)、Zn~(2+)、Hg~(2+)、Co~(2+)、Cd~(2+)、Ni~(2+)、Cu~(2+)、Mn~(2+)、Ag+、Pb~(2+)、Cr~(3+)、Fe~(2+))干扰。通过测定探针化合物F-1的离子选择性、离子竞争性、浓度梯度、Job’s曲线和pH对探针分子荧光强度的影响,发现在p H=5～7的环境中,Fe~(3+)浓度在2.0×10~(–6)～1.8×10~(–5) mol/L时,探针F-1对其检测呈较好的线性关系,其具备定性、定量检测生物机体或者环境中痕量Fe~(3+)的潜力。
A Rhodamine B derivative fluorescent probe F-1 〔 3',6'-bis(diethylamino)-2-phenylspiro[isoindoline-3,9'-xanthen]-3-one〕 was synthesized by condensation reaction of Rhodamine B with aniline.Its structure was characterized by 1 HNMR, 13 CNMR and HRMS. It was found that after Fe~(3+) was added into the probe system, the probe system changed from colorless to purple and the fluorescence intensity was significantly enhanced without interference from other metal ions(Na~+, K~+, Ca~(2+), Mg~(2+), Zn~(2+), Hg~(2+),Co~(2+), Cd~(2+), Ni~(2+), Cu~(2+), Mn~(2+), Ag+, Pb~(2+), Cr~(3+), Fe~(2+)). The effects of ion selectivity, ion competitiveness,concentration gradient, Job's plot and pH on the fluorescence intensity of probe F-1 were measured. The results showed that at pH=5～7, the probe F-1 presented a good linear relationship when Fe~(3+)concentration ranged from 2.0×10~(–6) to 1.8×10~(–5) mol/L, indicating that probe F-1 had the potential to qualitative and quantitative detection of trace Fe~(3+) in biological organisms or environment.
A Rhodamine B derivative fluorescent probe F-1 〔 3',6'-bis(diethylamino)-2-phenylspiro[isoindoline-3,9'-xanthen]-3-one〕 was synthesized by condensation reaction of Rhodamine B with aniline.Its structure was characterized by 1 HNMR, 13 CNMR and HRMS. It was found that after Fe~(3+) was added into the probe system, the probe system changed from colorless to purple and the fluorescence intensity was significantly enhanced without interference from other metal ions(Na~+, K~+, Ca~(2+), Mg~(2+), Zn~(2+), Hg~(2+),Co~(2+), Cd~(2+), Ni~(2+), Cu~(2+), Mn~(2+), Ag+, Pb~(2+), Cr~(3+), Fe~(2+)). The effects of ion selectivity, ion competitiveness,concentration gradient, Job's plot and pH on the fluorescence intensity of probe F-1 were measured. The results showed that at pH=5～7, the probe F-1 presented a good linear relationship when Fe~(3+)concentration ranged from 2.0×10~(–6) to 1.8×10~(–5) mol/L, indicating that probe F-1 had the potential to qualitative and quantitative detection of trace Fe~(3+) in biological organisms or environment.
引文
[1]Hua Z Q,Wang X M,Feng Y C,et al.Sulfonyl rhodamine hydrazide:A sensitive and selective chromogenic and fluorescent chemodosimeter for copper ion in aqueous media[J].Dyes and Pigments,2011,88(3):257-261.
[2]Lunvongsa S,Oshima M,Motomizu S.Determination of total and dissolved amount of iron in water samples using catalytic spectrophotometric flow injection analysis[J].Talanta,2006,68(3):969-973.
[3]Cabon J Y,Giamarchi P,Bihan A L.Determination of iron in seawater by electrothermal atomic absorption spectrometry and atomic fluorescence spectrometry:A comparative study[J].Analytica Chimica Acta,2010,664(2):114-120.
[4]Huang Yi(黄怡),Yang Meipan(杨美盼),Zhang Weihong(张卫红),et al.The study of a highly selective rhodamine Schiff base probe for Fe3+[J].Chemical Research and Application(化学研究与应用),2018,30(1):88-94.
[5]Afshani J,Badiei A,Jafari M,et al.A single optical sensor with high sensitivity for detection of Fe3+and CN-ions[J].Journal of Luminescence,2016,179(463):463-468.
[6]Qiao R,Xiong W Z,Bai C B,et al.A highly selective fluorescent chemosensor for Fe(Ⅲ)based on Rhodamine 6G dyes derivative[J].Supramolecular Chemistry,2018,30(1):1-7.
[7]Ow H,Larson D R,Srivastava M.Bright and stable core-shell fluorescent silica nanoparticles[J].Nano Lett,2005,5(1):113-117.
[8]Nathaniel C L,Svetlana V P,Christian B.Squaramide hydroxamate based chemidosimeter responding to iron(Ⅲ)with a fluorescence intensity in-crease[J].Inorg Chem,2009,48(3):1173-1182.
[9]Isabelle H A,Prashanth T,Beena B,et al.Increased risk of iron deficiency and reduced iron absorption but no difference in zinc,vitamin A or B-vitamin status in obese women in India[J].European Journal of Nutrition,2016,55(8):2411-2421.
[10]Pieter M,Frederik V,Petra N,et al.Impact of iron deficiency on response to and remodeling after cardiac resynchronization therapy[J].American Journal of Cardiology,2017,119(1):65-70.
[11]Jiang Y C,Sun Y Y,Gong W L,et al.Effects of iron owerload on growth and intestinal mucosa in rats[J].International Journal of Science,2017,3(3):57-61.
[12]Peng Mengjiao(彭梦姣).Synthesis and properties of novel hybrid fluorescent sensor for Fe(Ⅲ)detection[J].Chemistry(化学通报),2018,81(5):450-455.
[13]Dujols V,Ford F,Czarnik A W.A long-wavelength fluorescent chemodosimeter selective for Cu(Ⅱ)ion in water[J].Journal of the American Chemical Society,1997,119(31):7386-7387.
[14]Zhang R,Yan F,Huang Y,et al.Rhodamine-based ratiometric fluorescent probes based on excitation energy transfer mechanisms:construction and applications in ratiometric sensing[J].RSCAdvances,2016,6(56):50732-50760.
[15]Huang J H,Xua Y F,Qian X H.Rhodamine-based fluorescent off-on sensor for Fe3+in aqueous solution and in living cells:8-aminoquinoline receptor and 2:1 binding[J].Dalton Trans,2014,43(16):5983-5989.
[16]Yang Y X,Gao W L,Sheng R L,et al.Rhodamine-based derivatives for Cu2+sensing:Spectroscopic studies,structure-recognition relationships and its test strips[J].Spectrochimica Acta,Part A:Molecular and Biomolecular Spectroscopy,2011,81(1):14-20.
[17]Wang S X,Meng X M,Zhu M Z.A naked-eye rhodamine-based fluorescent probe for Fe(Ⅲ)and its application in living cells[J].Tetrahedron Letter,2011,52(22):2840-2843.
[18]Wang C C,Zhang D,Huang X Y,et al.A fluorescence ratiometric chemosensor for Fe3+based on TBET and its application in living cells[J].Talanta,2014,128:69-74.
[19]Liu J F,Qian Y.A novel pyridylvinyl naphthalimide-rhodamine dye:Synthesis,naked-eye visible and ratiometric chemodosimeter for Hg2+/Fe3+[J].Journal of Luminescence,2017,187:782-790.
[2]Lunvongsa S,Oshima M,Motomizu S.Determination of total and dissolved amount of iron in water samples using catalytic spectrophotometric flow injection analysis[J].Talanta,2006,68(3):969-973.
[3]Cabon J Y,Giamarchi P,Bihan A L.Determination of iron in seawater by electrothermal atomic absorption spectrometry and atomic fluorescence spectrometry:A comparative study[J].Analytica Chimica Acta,2010,664(2):114-120.
[4]Huang Yi(黄怡),Yang Meipan(杨美盼),Zhang Weihong(张卫红),et al.The study of a highly selective rhodamine Schiff base probe for Fe3+[J].Chemical Research and Application(化学研究与应用),2018,30(1):88-94.
[5]Afshani J,Badiei A,Jafari M,et al.A single optical sensor with high sensitivity for detection of Fe3+and CN-ions[J].Journal of Luminescence,2016,179(463):463-468.
[6]Qiao R,Xiong W Z,Bai C B,et al.A highly selective fluorescent chemosensor for Fe(Ⅲ)based on Rhodamine 6G dyes derivative[J].Supramolecular Chemistry,2018,30(1):1-7.
[7]Ow H,Larson D R,Srivastava M.Bright and stable core-shell fluorescent silica nanoparticles[J].Nano Lett,2005,5(1):113-117.
[8]Nathaniel C L,Svetlana V P,Christian B.Squaramide hydroxamate based chemidosimeter responding to iron(Ⅲ)with a fluorescence intensity in-crease[J].Inorg Chem,2009,48(3):1173-1182.
[9]Isabelle H A,Prashanth T,Beena B,et al.Increased risk of iron deficiency and reduced iron absorption but no difference in zinc,vitamin A or B-vitamin status in obese women in India[J].European Journal of Nutrition,2016,55(8):2411-2421.
[10]Pieter M,Frederik V,Petra N,et al.Impact of iron deficiency on response to and remodeling after cardiac resynchronization therapy[J].American Journal of Cardiology,2017,119(1):65-70.
[11]Jiang Y C,Sun Y Y,Gong W L,et al.Effects of iron owerload on growth and intestinal mucosa in rats[J].International Journal of Science,2017,3(3):57-61.
[12]Peng Mengjiao(彭梦姣).Synthesis and properties of novel hybrid fluorescent sensor for Fe(Ⅲ)detection[J].Chemistry(化学通报),2018,81(5):450-455.
[13]Dujols V,Ford F,Czarnik A W.A long-wavelength fluorescent chemodosimeter selective for Cu(Ⅱ)ion in water[J].Journal of the American Chemical Society,1997,119(31):7386-7387.
[14]Zhang R,Yan F,Huang Y,et al.Rhodamine-based ratiometric fluorescent probes based on excitation energy transfer mechanisms:construction and applications in ratiometric sensing[J].RSCAdvances,2016,6(56):50732-50760.
[15]Huang J H,Xua Y F,Qian X H.Rhodamine-based fluorescent off-on sensor for Fe3+in aqueous solution and in living cells:8-aminoquinoline receptor and 2:1 binding[J].Dalton Trans,2014,43(16):5983-5989.
[16]Yang Y X,Gao W L,Sheng R L,et al.Rhodamine-based derivatives for Cu2+sensing:Spectroscopic studies,structure-recognition relationships and its test strips[J].Spectrochimica Acta,Part A:Molecular and Biomolecular Spectroscopy,2011,81(1):14-20.
[17]Wang S X,Meng X M,Zhu M Z.A naked-eye rhodamine-based fluorescent probe for Fe(Ⅲ)and its application in living cells[J].Tetrahedron Letter,2011,52(22):2840-2843.
[18]Wang C C,Zhang D,Huang X Y,et al.A fluorescence ratiometric chemosensor for Fe3+based on TBET and its application in living cells[J].Talanta,2014,128:69-74.
[19]Liu J F,Qian Y.A novel pyridylvinyl naphthalimide-rhodamine dye:Synthesis,naked-eye visible and ratiometric chemodosimeter for Hg2+/Fe3+[J].Journal of Luminescence,2017,187:782-790.