苯并噻唑类荧光探针的合成及对N_2H_4·H_2O和HSO_3~-的检测性能
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摘要
以苯并噻唑为荧光团,氰基乙酸乙酯为识别基团,设计合成了对水合肼和亚硫酸氢盐具有双重检测能力的荧光探针3-(2-羟基-苯并噻唑)-2-氰基-丙烯酸乙酯(HBT-CN).在二甲基亚砜/磷酸盐(体积比为1∶4)的缓冲液中,探针对水合肼和亚硫酸氢盐具有良好的选择性,且荧光强度分别增强了5. 6倍(500 nm)和7. 5倍(458 nm).结果表明,在检测过程中,HTB-CN与水合肼发生了还原-缩合反应,生成了醛腙,在波长500 nm处发出黄绿色的荧光信号; HBT-CN与亚硫酸氢盐发生了亲核加成反应,在波长458 nm处发出蓝色的荧光信号,从而实现了对水合肼和亚硫酸氢盐的差异性定性与定量检测.
Based on benzothiazole as fluorophore,ethyl cyanoacetate as recognition group,a new fluorescent probe 3-( 2-hydroxy-benzothiazole)-2-cyano-ethyl acrylate( HBT-CN) with dual detection ability for hydrazine hydrate and bisulfite was designed and synthesized. In DMSO/PBS( 1 ∶ 4,volume ratio) buffered condition,the probe displayed good selectivity towards hydrazine and bisulfite with approximate 5. 6 times( 500 nm) and7. 5 times( 458 nm) fluorescence enhancement at 500 and 458 nm,respectively.~1H NMR,~(13)C NMR and HRMS results showed that during the detection process,HBT-CN undergoed a reduction-condensation reaction with N_2H_4·H_2O,which form a aldehyde hydrazone and emited pale yellow fluorescent signal at 500 nm. And HBT-CN under went a nucleophilic addition reaction with bisulfite and emited blue fluorescent signal at 458 nm. So,differential qualitative and quantitative detection of N_2H_4·H_2O and HSO_3~-can be achieved.
Based on benzothiazole as fluorophore,ethyl cyanoacetate as recognition group,a new fluorescent probe 3-( 2-hydroxy-benzothiazole)-2-cyano-ethyl acrylate( HBT-CN) with dual detection ability for hydrazine hydrate and bisulfite was designed and synthesized. In DMSO/PBS( 1 ∶ 4,volume ratio) buffered condition,the probe displayed good selectivity towards hydrazine and bisulfite with approximate 5. 6 times( 500 nm) and7. 5 times( 458 nm) fluorescence enhancement at 500 and 458 nm,respectively.~1H NMR,~(13)C NMR and HRMS results showed that during the detection process,HBT-CN undergoed a reduction-condensation reaction with N_2H_4·H_2O,which form a aldehyde hydrazone and emited pale yellow fluorescent signal at 500 nm. And HBT-CN under went a nucleophilic addition reaction with bisulfite and emited blue fluorescent signal at 458 nm. So,differential qualitative and quantitative detection of N_2H_4·H_2O and HSO_3~-can be achieved.
引文
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[4]Christopher A.R.,Steven D.A.,Chem.Res.Toxicol.,1997,10,328-334
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[7]Mahmoud A.A.T.,Hassan G.M.,Hassan A.M.S.,Abdel Latif A.K.M.,Ramadan M.F.,Eur.J.Integ.Med.,2015,7,234-242
[8]Wang H.,Wu X.,Yang S.,Tian H.,Liu Y.,Sun B.,Dyes and Pigments,2019,160,757-764
[9]Ao H.,Zhang Y.,Plant Physiology Communication,2007,43(2),259-263(敖红,张羽.植物生理学通讯,2007,43(2),259-263)
[10]Li G.,Sang N.,Ecotox.Environ.Safe.,2009,72,236-241
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[12]Dutta T.,Chandra F.,Koner A.L.,Spectrochim.Acta Part A,2018,191,217-220
[13]Zhao F.,Sultanbawa Y.,Feng H.,Wang Y.L.,Meng Q.T.,Wang Y.,Zhang Z.Q.,Zhang R.,J.Agric.Food Chem.,2019,67,4375-4383
[14]Michigami Y.,Morooka M.,Ueda K.,J.Chromatogr.A,1996,732(2),403-407
[15]Malone H.E.,Anal.Chem.,1961,33,575-577
[16]Isaac A.,Wain A.J.,Compton R.G.,Livingstone C.,Davis J.,The Analyst.,2005,130,1343-1344
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[18]Elder D.P.,Snodin D.,Teasdale A.,J.Phar.Biome.Analysis,2011,54,900-910
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[21]Ding Y.B.,Tang Y.Y.,Zhu W.H.,Xie Y.S.,Chem.Soc.Rev.,2015,44,1101-1112
[22]Ding Y.B.,Li X.,Li T.,Zhu W.H.,Xie Y.S.,J.Org.Chem.,2013,78,5328-5338
[23]Shi X.,Yin C.,Wen Y.,Zhang Y.,Huo F.,Spectro.Acta Part A,2018,203,106-111
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[28]Zhang H.,Feng W.,Feng G.,Dyes and Pigments,2017,139,73-78
[29]Gu B.,Huang L.,Su W.,Duan X.,Li H.,Yao S.,Anal.Chim.Acta,2017,954,97-104
[30]Zhou Y.,Zeng F.,Liu Y.,Li M.,Xiao S.,Yan J.,Zhang N.,Zheng K.,Tetrah.Letters,2018,59,3253-3257
[31]Wang S.J.,Li J.,Gao Y.,Guo Y.,Asian J.Org.Chem.,2018,7,563-569
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