摘要
以4-氨基安替比林与2-(4-甲基吡啶)-2-异烟酸醛缩合反应得到新型安替比林衍生物(E)-1,5-二甲基-4-((2-(4-甲基吡啶-2-基)吡啶-4-基)亚甲基氨基)-2-苯基-1,2-二氢吡唑-3-酮(L),并对其光学、金属离子选择性识别性能和单晶结构进行了研究。发现L在水-乙醇(9∶1,V/V)溶液中,能选择性比色和肉眼识别Fe~(2+),且受常见金属离子的干扰较小。用Job法得到Fe~(2+)与L的化学计量比为1∶3([FeL_3]~(2+)),配合物的缔合常数为3.70×1021 L3·mol-3,检测限为0.094μmol·L~(-1)。结果表明,化学传感器L可作为一种有选择性、灵敏的Fe~(2+)比色传感器。
An aminoantipyrine based chemosensor,(E)-1,5-dimethyl-4-((2-(4-methylpyridin-2-yl)pyridin-4-yl)methyleneamino)-2-phenyl-1,2-dihydropyrazol-3-one(L), derived from 4-aminoantipyrine and 2-(4-methylpyridin-2-yl) isonicotinaldehyde, was synthesized and the optical and metal sensing properties were investigated. The chemosensor L showed a selective colorimetric sensing ability for Fe~(2+)by changing colors from pale yellow to deep red in water-ethanol(9∶1, V/V) medium, which facilitates the ‘naked-eye' recognition of Fe~(2+)from other examined metal ions. The complex stoichiometry of Fe~(2+)to L(1∶3, [FeL_3]~(2+)) was obtained by Job′s method. The association constant was determined to be 3.70×1021 L3·mol~(-3). The present results indicate that the chemosensor L could be used as a selective, sensitive colorimetric sensor for Fe~(2+). CCDC: 1817471, L.
引文
[1]Pierre J L,Fontecave M,Crichton R R.Biometals,2002,15:341-346
[2]Frausto da Silva J J R,Williams R J P.The Biological Chemistry of the Elements:the Inorganic Chemistry of Life.Oxford:Clarendon Press,1991:101
[3]Bertini I,Gray H B,Lippard S J,et al.Bioinorganic Chemistry.Mill Valley:University Science Book,1994.
[4]Nolan E M,Lippard S J.Chem.Rev.,2008,108:3443-3480
[5]Domaille D W,Que E L,Chang C J.Nat.Chem.Biol.,2008,4:168-175
[6]Silva A P,Fox D B,Huxley A J M,et al.Chem.Rev.,2000,205:41-57
[7]Czarnik A.Fluorescent Chemosensors for Ion and Molecule Recognition.Washington,DC:American Chemical Society,1992.
[8]Kim H M,Cho B R.Acc.Chem.Res.,2009,42:863-872
[9]Matzanke B F,Muller-Matzanke G,Raymond K N.Iron Carriers and Iron Proteins:Vol.5.Loehr T M.Ed.,New York:VCH,1989.
[10]Gray H B,Winkler J R.Annu.Rev.Biochem.,1996,65:537-561
[11]Kaplan C D,Kaplan J.Chem.Rev.,2009,109:4536-4552
[12]Okonko D O,Grzeslo A,Witkowski T,et al.J.Am.Coll.Cardiol.,2008,51:103-112
[13]Freixenet N,Vilardell C,Llaurad G,et al.Diabetes Res.Clin.Pract.,2011,91:33-36
[14]McLaren C E,Gordeuk V R,Chen W P,et al.Transl.Res.,2008,151:97-109
[15]Dixon S J,Lemberg K M,Lamprecht M R.Cell,2012,149:1060-1072
[16]Yu H,Guo P,Xie X.J.Cell Mol.Med.,2017,21:648-657
[17]Zhu C C,Wang M J,Qiu L,et al.Dyes Pigm.,2018,157:328-333
[18]Canfranc E,Abarca A,Sierra I,et al.J.Pharm.Biomed.Anal.,2001,25:103-108
[19]Tangen G,Wickstrm T,Lierhagen S,et al.Environ.Sci.Technol.,2002,36:5421-5425
[20]Oh J W,Kim T H,Yoo S W,et al.Sens.Actuators A,2013,177:813-817
[21]Lee J A,Eom G H,Park H M,et al.J.Korean Chem.Soc.,2012,33:3625-3628
[22]YUAN Yue-Hua(袁跃华),TIAN Mao-Zhong(田茂忠),FENGFeng(冯锋),et al.Progress in Chemistry(化学进展),2010,22(10):1929-1939
[23]QIU Lin(邱琳),JI Yi-Fan(季一凡),ZHU Cheng-Cheng(朱成成),et al.Chinese J.Inorg.Chem.(无机化学学报),2014,30(1):169-178
[24]Zhang Y Y,Chen X Z,Liu X Y,et al.Sens.Actuators B,2018,273:1077-1084
[25]Choa C H C C,Wan C F,Wu A T.Inorg.Chem.Commun.,2014,41:88-91
[26]Wang S,Gwon S Y,Kim S H.Spectrochim.Acta Part A,2010,76:293-296
[27]Tamil S G,Kumaresan M,Sivaraj R,et al.Sens.Actuators B,2016,229:181-189
[28]Zhou Y,Zhou H,Zhang J,et al.Spectrochim.Acta Part A,2012,98:14-17
[29]Xiong J J,Huang P C,Zhang C Y,et al.Sens.Actuators B,2016,226:30-36
[30]Hao Z Y,Liu Q W,Xu J,et al.Chem.Pharma.Bull.,2010,58:1306-1312
[31]Siddan P,Somasundharam S P.Tetrahedron Lett.,2015,56:5920-5923
[32]Wang Y W,Zhang Y,Zhu D R,et al.Spectrochim.Acta Part A,2015,147:31-42
[33]Grynkiewcz G,Poenie M,Tsein R Y.J.Biol.Chem.,1985,260:3440-3450
[34]Dixon I M,Khan S,Alary F,et al.Dalton Trans.,2014,43:15898-15905
[35]John P P,Matthias E,Kieron B.J.Chem.Phys.,1996,105:9982-9985
[36]Frisch M J,Trucks G W,Schlegel H B,et al.Gaussian 09,Revision A.02,Gaussian Inc,Wallingford,CT,2009.
[37]Dennington R,Keith T,Millam J.GaussView,Semichem Inc.,Shawnee Mission,KS,2009.
[38]Zhou X,Yu B,Guo Y,et al.Inorg.Chem.,2010,49:4002-4007