基于咔唑和间苯二甲酸的荧光配体合成及性能
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摘要
以咔唑、5-羟基-1,3-苯二甲酸二乙酯和1,4-二溴丁烷为原料,经缩合、水解等步骤合成了一种新型荧光配体N-[4-(3,5-二羧基苯氧基)-丁基]咔唑,并利用傅里叶变换红外光谱、核磁共振氢谱及单晶X-射线衍射对其结构进行了表征,该化合物具有很强的荧光特性。在乙醇/水混合介质中,Fe3+的存在会导致化合物的荧光强度显著降低,显示出高效的Fe3+选择性"开-关"行为。最大淬灭率达到86%,这种强的荧光淬灭效应是化合物和Fe3+离子发生配位作用的结果。荧光滴定实验和体系红外光谱数据表明,在溶液中,化合物与Fe3+之间的结合是一种多分子的协同配位模式。
A new fluorescent ligand,N-[4-( 3,5-dicarboxylphenoxy)-butyl]-carbazole was synthesized from carbazole,diethyl 5-hydroxyisophthalate and 1,4-dibromobutane through condensation and hydrolysis. And its molecular structure was confirmed by Fourier transform infrared spectroscopy,proton nuclear magnetic resonance spectra and X-ray single-crystal diffraction.This compound has strong fluorescence property.In ethanol/water solution,the fluorescence intensity at 352 nm decreased significantly in the presence of Fe3+due to the coordination with Fe3+ion,indicating an efficient Fe3+-selective"on-off"behavior.The quenching rate was up to 86%.The results of fluorescence titration experiment and infrared spectroscopy of the system indicated a polymolecular cooperative coordination binding mode between the compound and Fe3+.
A new fluorescent ligand,N-[4-( 3,5-dicarboxylphenoxy)-butyl]-carbazole was synthesized from carbazole,diethyl 5-hydroxyisophthalate and 1,4-dibromobutane through condensation and hydrolysis. And its molecular structure was confirmed by Fourier transform infrared spectroscopy,proton nuclear magnetic resonance spectra and X-ray single-crystal diffraction.This compound has strong fluorescence property.In ethanol/water solution,the fluorescence intensity at 352 nm decreased significantly in the presence of Fe3+due to the coordination with Fe3+ion,indicating an efficient Fe3+-selective"on-off"behavior.The quenching rate was up to 86%.The results of fluorescence titration experiment and infrared spectroscopy of the system indicated a polymolecular cooperative coordination binding mode between the compound and Fe3+.
引文
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[6]XIANG Yu,TONG Ai-jun.A new rhodamine-based chemosensor exhibiting selective FeⅢ-amplified fluorescence[J].Org.Lett.,2006,8(8):1 549-1 552.
[7]BORDINI J,CALANDRELI I,SILVA G O,et al.A rhodamine-B-based turn-on fluorescent sensor for biological iron(Ⅲ)[J].Inorg.Chem.Commun.,2013,35:255-259.
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[9]CHEN C T,HUANG Wan-pei.A highly selective fluorescent chemosensor for lead ions[J]. J. Am. Chem. Soc.,2002,124(22):6 246-6 247.
[10]JUNG H S,KWON P S,LEE J W,et al.Coumarin-derived Cu2+-selective fluorescence sensor:synthesis,mechanisms,and applications in living cells[J]. J. Am.Chem.Soc.,2009,131(5):2 008-2 012.
[11]YAO Jun-na,DOU Wei,QIN Wen-wu,et al.A new coumarin-based chemosensor for Fe3+in water[J]. Inorg.Chem.Commun.,2009,12(2):116-118.
[12]JISHA V S,THOMAS A J,RAMAIAH D.Fluorescence ratiometric selective recognition of Cu2+ions by dansylnaphthalimide dyads[J]. J. Org. Chem.,2009,74(17):6 667-6 673.
[13]PARKESH R,LEE T C,GUNNLAUGSSON T. Highly selective 4-amino-1,8-naphthalimide based fluorescent photoinduced electron transfer(PET)chemosensors for Zn(Ⅱ)under physiological p H conditions[J].Org.Biomol.Chem.,2007,5(2):310-317.
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[15]MARTINEZ-MANEZ R,SANCENON F.Fluorogenic and chromogenic chemosensors and reagents for anions[J].Chem.Rev.,2003,103(11):4 419-4 476.
[16]ALI A,ZHANG Qi,DAI Ji-sen,et al.Calcein as a fluorescent iron chemosensor for the determination of low molecular weight iron in biological fluids[J]. Bio. Metals,2003,16(2):285-293.
[17]ZHANG Meng,GAO Yan-hong,LI Man-yu,et al.A selective turn-on fluorescent sensor for FeⅢand application to bioimaging[J].Tetra.Lett.,2007,48(21):3 709-3 712.
[18]ZHANG Xin,WU Yu-bo,JI Shao-min,et al.Effect of the electron donor/acceptor orientation on the fluorescence transduction efficiency of the d-PET effect of carbazolebased fluorescent boronic acid sensors[J]. J. Org.Chem.,2010,75(8):2 578-2 588.
[19]CHANG C C,KUO I C,LING I F,et al. Detection of quadruplex DNA structures in human telomeres by a fluorescent carbazole derivative[J]. Anal. Chem.,2004,76(15):4 490-4 494.
[20]DANJOU P E,LYSKAWA J,DELATTRE F,et al.New fluorescent and electropolymerizable N-azacrown carbazole as a selective probe for iron(Ⅲ)in aqueous media[J]. Sensor Actuat. B-Chem.,2012,171/172:1 022-1 028.
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[22]HE Ya-bing,LI Bin,O'KEEFFE M,et al.Multifunctional metal-organic frameworks constructed from metabenzenedicarboxylate units[J].Chem.Soc. Rev.,2014,43(16):5 618-5 656.
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[25]CI Yun-xiang,JIA Xin.Determination of relative fluorescence quantum yields using a simplified method[J].Chin.J.Anal.Chem.,1986,14(8):616-618.
[26]GLASS T E.Cooperative chemical sensing with bis-tritylacetylenes:pinwheel receptors with metal ion recognition properties[J]. J. Am. Chem. Soc.,2000,122(18):4 522-4 523.
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