CN108299293A - 氰化物/氰化氢的比色-荧光探针化合物及其制备方法 - Google Patents

氰化物/氰化氢的比色-荧光探针化合物及其制备方法 Download PDF

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CN108299293A
CN108299293A CN201810136387.1A CN201810136387A CN108299293A CN 108299293 A CN108299293 A CN 108299293A CN 201810136387 A CN201810136387 A CN 201810136387A CN 108299293 A CN108299293 A CN 108299293A
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cyanide
quinoline
malononitrile
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宋钦华
钟琳
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University of Science and Technology of China USTC
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Abstract

本发明公开了一种氰化物/氰化氢的比色‑荧光探针化合物2‑(6‑(N,N‑二乙氨基)喹啉‑2‑甲撑)丙二腈及其制备方法，特征是以乙腈为反应介质，将6‑(二乙基氨基)喹啉‑2‑甲醛和丙二腈按1:1.0～2.0摩尔比，并加入1滴哌啶，在室温、氮气保护下搅拌反应30～60分钟；减压下除去乙腈，快速柱层析，分离即得到探针化合物2‑(6‑(N,N‑二乙氨基)喹啉‑2‑甲撑)丙二腈。利用本发明的比色‑荧光探针化合物2‑(6‑(N,N‑二乙氨基)喹啉‑2‑甲撑)丙二腈，首次实现了比色、比率荧光检测氰化物和氰化氢气体，与现有探针在氰化物检测领域的技术相比，响应时间快，检测限低，选择性高。

Description

氰化物/氰化氢的比色-荧光探针化合物及其制备方法
技术领域
本发明属于氰化物(CN-)/氰化氢(HCN)检测技术领域，具体涉及用于检测氰化物(CN-)/氰化氢(HCN)的探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈及其制备方法。
背景技术
氰化物是一种剧毒物质，非常容易被人体吸收，可经口、呼吸道或皮肤进入人体。氰化物进入血液中可与细胞色素氧化酶的活性位点结合形成稳定的化合物，从而抑制线粒体呼吸链，导致细胞缺氧、窒息死亡。据《院外急救与灾害医学》(M.E.Keim,Terrorisminvolving cyanide:the prospect of improving preparedness in the prehospitalsetting,Prehospital andDisasterMedicine 21(2006)s56–s60.)的信息，氰化氢气体曾在二战中被用作大规模杀伤性武器，属于血液类化学战剂。氰化物在工业生产中被广泛使用，与酸接触后即产生氰化氢气体，这对环境和人身安全造成严重的威胁。因此，对氰离子和氰化氢气体的检测备受关注。
到目前为止，已提出的各种检测氰离子方法中的大多需要昂贵的仪器和复杂的操作。比色法或荧光法与其他方法相比具有耗费低、便捷，操作简单等优点。然而，在已公开的有关氰离子检测文献中，如英国《皇家化学会》((1)Chem.Soc.Rev.2014,43,4312,Recentprogress in the development of fluorometric and colorimetric chemosensors fordetection of cyanide ions.(2)RSC Adv.2015,5,49953,A simple Michael acceptortype quinoline derivative for highly selective sequential recognition of CN-and Cu2+in aqueous solution.)中所提及的绝大多数探针分子都只能用于溶液中氰离子的检测，几乎没有比色和荧光法同时检测氰离子和氰化氢气体的探针分子。根据荷兰《爱思唯尔》和英国《皇家化学会》仅有的几篇比色法检测氰化氢气体的探针分子报道(根据检索相关文献:(1)Sens.Actuators B 2018,255,2750,M.S.Ibeas,F.Serna,F.C.J.M.Palladium-containing polymers as hybridsensory materials (water-soluble polymers,films and smart textiles)for thecolorimetric detection of cyanide in aqueous and gas phases.(2)Sens.ActuatorsB 2011,155,692,M.Yang,J.He,X.Hu,C.Yan,Z.Cheng,Y.Zhao,G.Zuo,Copper oxidenanoparticle sensors for hydrogen cyanide detection:Unprecedented selectivityand sensitivity.(3)Chem.Commun.2013,49,5669,R.Gotor,A.M.Costero,S.Gil,M.Parra,M.M.F.P.Selective and sensitivechromogenicdetection ofcyanide and HCN in solution and in gas phase.)可知，上述比色法检测氰化氢气体的探针分子在应用时也存在一定的缺陷，如探针对氰化氢气体的响应太慢，这严重制约了此类方法在实际中的应用。
发明内容
本发明的目的是针对现有技术中存在的问题，提供一种氰化物/氰化氢的比色-荧光探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈及其制备方法，以克服现有技术的上述缺陷。
本发明的氰化物/氰化氢的比色-荧光探针化合物，其特征在于是结构式为
的2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈。
其核磁共振氢谱是：1H NMR(400MHz,CDCl3):δ＝7.98(d,J＝9.54,1H),7.88(d,J＝8.60,1H),7.82(s,1H),7.64(d,J＝8.60,1H),7.35(dd,J＝9.56,2.88,1H),6.70(d,J＝2.68,1H),3.54(q,J＝7.12,4H),1.28(t,J＝7.12,6H)ppm；
其核磁共振碳谱是：13C NMR(100MHz,CDCl3):δ＝157.8,148.4,143.1,142.0,133.1,131.9,123.1,120.2,114.7,113.2,102.4,81.9,44.8,12.6ppm；
其高分辨质谱是：HRMS(ESI)m/z:[M+H]+calcd.for C17H16N4277.1448；found:277.1452。
本发明的氰化物/氰化氢的比色-荧光探针化合物的制备方法，其特征在于：以乙腈为反应介质，将6-(二乙氨基)喹啉-2-甲醛和丙二腈按1:1.0～2.0摩尔比，并加入1滴哌啶，在室温、氮气保护下搅拌反应30～60分钟；减压下除去乙腈，快速柱层析，分离得到的即为探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈。
上述探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈的合成路线可表示为：
本发明的上述探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈的乙腈溶液为红色，在365nm的手提紫外灯下有强烈的红色荧光；向溶液中加入氰离子后，溶液的颜色变为无色，荧光颜色变为蓝色；当含有2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈的检测膜暴露在HCN气体环境中时，10分钟内，检测膜的颜色从红色变为黄色，在365nm的手提紫外灯下荧光颜色由红色变为蓝绿色。肉眼可检测到的HCN气体浓度为60ppm。
与现有探针在氰化物检测领域的技术相比，本发明的探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈的制备方法简单，仅需一步反应即可制得，反应条件温和，操作简便。利用本发明的探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈具有比色、比率荧光检测氰化物和氰化氢气体的特征，首次实现了比色和荧光法同时检测氰化氢气体，并且响应时间快，检测限低，选择性高。
附图说明
图1是本发明的探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈(10×10- 6mol/L)在溶液中与加入氰离子(3当量)或其他阴离子(10当量)后的紫外-可见吸收光谱图。
图2是探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈(10×10-6mol/L)在溶液中与加入氰离子(3当量)和其他阴离子(10当量)后的荧光光谱图。
图3是在乙腈-水(95:5，v/v)溶液中探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈(10×10-6mol/L)与各种阴离子(10当量)对CN-(3当量)的荧光强度的干扰柱状图。
图4是在可见(左)、紫外灯(365nm)(右)下，检测膜暴露在不同浓度的HCN气体(0-85ppm)中的照片。
图5是在可见(左)、紫外灯(365nm)(右)下，检测膜暴露在不同气体环境(HCN：85ppm，其他气体：850ppm)下的照片。
具体实施方式
下面通过具体实施例进一步详细说明本发明氰化物/氰化氢的比色-荧光探针及其制备方法。
实施例1：探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈的合成
按照探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈的下列合成路线进行反应：
室温条件下，将6-(二乙氨基)喹啉-2-甲醛(100mg,0.44mmol)和丙二腈(59mg,0.88mmol)溶于5mL乙腈中，在氮气保护下用注射器加入1滴哌啶，室温搅拌反应30分钟；反应结束后减压蒸馏除去乙腈，柱层析分离(石油醚：乙酸乙酯＝10:1,v/v)得到产物红棕色固体50mg，产率41％。
本实施例中所制备得到的红棕色固体产物，其核磁共振氢谱是：1H NMR(400MHz,CDCl3):δ＝7.98(d,J＝9.54,1H),7.88(d,J＝8.60,1H),7.82(s,1H),7.64(d,J＝8.60,1H),7.35(dd,J＝9.56,2.88,1H),6.70(d,J＝2.68,1H),3.54(q,J＝7.12,4H),1.28(t,J＝7.12,6H)ppm；
其核磁共振碳谱是：13C NMR(100MHz,CDCl3):δ＝157.8,148.4,143.1,142.0,133.1,131.9,123.1,120.2,114.7,113.2,102.4,81.9,44.8,12.6ppm；
其高分辨质谱是：HRMS(ESI)m/z:[M+H]+calcd.for C17H16N4277.1448；found:277.1452。
由此证明了得到的红棕色固体产物是结构式为
的2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈。
实施例2：探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈的合成
将6-(二乙氨基)喹啉-2-甲醛(100mg,0.44mmol)和丙二腈(44mg,0.66mmol)溶于5mL乙腈中，在氮气保护下用注射器加入1滴哌啶，室温搅拌反应45分钟；反应结束后减压蒸馏除去乙腈，柱层析分离(石油醚:乙酸乙酯＝10:1,v/v)得到产物红棕色固体42mg，产率35％。
本实施例中所制备得到的红棕色固体产物，根据其核磁共振氢谱、核磁共振碳谱和高分辨质谱证明该固体产物就是2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈。
实施例3：探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈的合成
将6-(二乙氨基)喹啉-2-甲醛(100mg,0.44mmol)和丙二腈(29mg,0.44mmol)溶于5mL乙腈中，在氮气保护下用注射器加入1滴哌啶，室温搅拌反应60分钟；反应结束后减压蒸馏除去乙腈，柱层析分离(石油醚:乙酸乙酯＝10:1,v/v)得到产物红棕色固体30mg，产率25％。本实施例中所制备得到的红棕色固体产物，根据其核磁共振氢谱、核磁共振碳谱和高分辨质谱证明该固体产物就是2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈。
实施例4：探针的阴离子识别实验
1、探针的阴离子识别
分别移取12.5μL探针的乙腈溶液(2×10-3mol/L)于一系列5mL比色皿中，再分别移取125μL的蒸馏水于上述加了探针的比色皿中，然后再分别加入15μL 5×10-3mol/L的CN–乙腈溶液,25μL 10×10-3mol/L的氟离子,氯离子,溴离子,碘离子,磷酸氢根,硫氢根,硝酸根,亚硝酸根,硫酸根,亚硫酸氢根,高氯酸根,溴酸根和氯酸根水溶液。用乙腈稀释至2.5mL，此时探针浓度为10×10-6mol/L，CN–的浓度为探针浓度的3倍，其他阴离子浓度为探针浓度的10倍，混合均匀后放置30分钟左右，观察探针对各种阴离子的响应。
图1为探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈(10×10-6mol/L)在溶液中与加入氰离子(3当量)或其他阴离子(10当量)后的紫外-可见吸收光谱图。从图1中可见，当在探针化合物的乙腈-水(95:5，v/v)溶液中分别加入上述阴离子的乙腈溶液或水溶液时，CN–的加入使探针的乙腈溶液由红色变为无色。在其相应的紫外-可见吸收光谱中，CN–的加入使探针在500nm处的吸收峰几乎消失。其他阴离子的加入对探针的乙腈溶液颜色和紫外-可见吸收光谱无明显影响。图2为探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈(10×10-6mol/L)在溶液中与加入氰离子(3当量)和其他阴离子(10当量)后的荧光光谱图。从图2中可见，探针溶液在430nm波长光激发下显红色荧光，在相应的荧光光谱中，在622nm处有很强的荧光发射峰，CN–的加入使探针的红色荧光迅速猝灭，在622nm处的荧光峰几乎消失，且蓝移到488nm，发出蓝色荧光。上述现象说明该探针对CN–具有裸眼可见且专一选择性的响应。
2、抗干扰性检测
测试方法：在第一个比色皿中仅移入12.5μL探针的乙腈溶液(2×10-3mol/L)且用乙腈-水溶液(95:5，v/v)定容至2.5mL。在第二个比色皿中加入12.5μL探针的乙腈溶液(2×10-3mol/L)和15μL CN–的乙腈溶液(5×10-3mol/L)，然后定容至2.5mL。在剩下的十三个5mL比色皿中分别加入12.5μL探针的乙腈溶液(2×10-3mol/L)，然后分别移取氟离子,氯离子,溴离子,碘离子,磷酸氢根,硫氢根,硝酸根,亚硝酸根,硫酸根,亚硫酸氢根,高氯酸根,溴酸根和氯酸根水溶液的水溶液(10×10-3mol/L)25μL，再分别移取15μL CN–的乙腈溶液(5×10-3mol/L)于上述比色皿中，最后定容至2.5mL。将上述十五个比色皿中的溶液混合均匀后放置30分钟后进行观察。
图3为在乙腈-水(95:5，v/v)溶液中探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈(10×10-6mol/L)与各种阴离子(10当量)对CN–(3当量)的荧光干扰柱状图；其中纵坐标为荧光强度比值，横坐标为干扰离子，横坐标上标的数字1处代表探针，数字2-15分别代表探针+各种干扰阴离子，其中：2为氰离子，3为氟离子，4为氯离子，5为溴离子，6为碘离子，7为磷酸氢根，8为硫氢根，9为硝酸根，10为亚硝酸根，11为硫酸根，12为亚硫酸氢根，13为高氯酸根，14为溴酸根，15为氯酸根。结果显示，第一个比色皿溶液呈红色为探针的颜色，其余加了CN–的溶液颜色均变为无色。根据荧光峰强度的比例(I488/I622)的柱状图(图3)可以看到，其他离子的加入对CN–的识别过程基本没有影响。说明探针对CN–的识别不受到这些离子的干扰。
实施例5：HCN检测膜的制备及应用
1、HCN检测膜的制备
将1.5mg探针化合物溶解在40mL二氯甲烷(DCM)中，然后再加入1.8g聚氧化乙烯，在室温下搅拌直至溶液透明、均匀。随后，将溶液转移至干燥的直径为7.5cm的培养皿中，并放置在干燥箱中，在40℃下使溶剂挥发至干。最后将膜剪成1.0cm×0.5cm的大小，即可得到HCN检测膜。
2、HCN检测膜对HCN气体的检测
将上述1.0cm×0.5cm大小的检测膜粘在10mL离心管中，即可制成HCN气体的检测管。将1.0mg氰化钠(NaCN)溶解在2mL蒸馏水中，得到10mM的NaCN溶液。用微量进样器向2-6号试剂管中分别移取10μL,20μL,30μL,40μL和50μL上述NaCN溶液，随后加入50μL 98％的浓硫酸并迅速关闭离心管。图4为在可见(左)、紫外灯(365nm)(右)下，检测膜暴露在不同浓度的HCN气体(0-85ppm)环境下的照片。如图4所示，试剂管中的检测膜从红色变为黄色；在紫外灯下(365nm)，膜从红色荧光变成蓝绿色荧光，说明试剂管中产生了HCN气体。其中1号试剂管内只有检测膜，作为参照。根据化学反应式计算，忽略HCN在溶液中的溶解度，可以得到六根试剂管中，HCN气体的浓度分别为0ppm,23ppm,43ppm,60ppm,75ppm和85ppm。
HCN检测膜的气体识别实验
称取4.7mg二水合氟化钾、5.1mg溴化钠、8.3mg碘化钾、5.0mg碳酸钙、6.3mg亚硫酸钠和4.0mg硫化钠分别用500μL蒸馏水溶解在离心管中，作为储备液。用微量进样器向3-8号试剂管中分别移取50μL上述溶液和50μL 98％的硫酸，向9号试剂管中移入5μL盐酸。1号试剂管内只有检测膜，作为参照，2号试剂管内移入50μL上述NaCN储备液和50μL 98％的硫酸。图5为在可见(左)、紫外灯(365nm)(右)下，检测膜暴露在不同气体环境(HCN：85ppm，其他气体：850ppm)下的照片。如图5所示，只有2号试剂管中的膜为黄色，在紫外灯下(365nm)，膜的荧光颜色为蓝绿色，说明该检测膜对HCN气体有很好的选择性。
由上可见，与现有探针在氰化物检测领域的技术相比，本发明的探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈的制备方法简便，仅需一步反应即可制得，反应条件温和，操作简单。利用本发明的探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈具有比色、比率荧光检测氰化物和氰化氢气体的特征，首次实现了比色和荧光法同时检测氰化氢气体，并且响应时间快，检测限低，选择性高。

Claims (2)

1.一种氰化物/氰化氢的比色-荧光探针化合物，其特征在于是结构式为
的2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈。
2.权利要求1所述氰化物/氰化氢的比色-荧光探针化合物的制备方法，其特征在于：以乙腈为反应介质，将6-(二乙氨基)喹啉-2-甲醛和丙二腈按1:1.0～2.0摩尔比，并加入1滴哌啶，在室温、氮气保护下搅拌反应30～60分钟；减压下除去乙腈，快速柱层析，分离得到的即为探针化合物2-(6-(N,N-二乙氨基)喹啉-2-甲撑)丙二腈。
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