CN104892504B - 一种能连续识别CN‑和Cu2+的传感器分子及其合成和应用 - Google Patents
一种能连续识别CN‑和Cu2+的传感器分子及其合成和应用 Download PDFInfo
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Abstract
本发明计合成了一种基于2‑(喹啉‑2‑甲烯基)丙二腈的荧光传感器,属于化学合成技术领域和离子检测技术领域。该传感器分子的合成是以乙醇为溶剂,丙二腈和喹啉二甲醛为底物进行回流反应;反应完成后冷却至室温,抽滤,干燥后用乙醇重结晶,得到紫黑色针状固体即得,其结构简单,合成方法简便,只需一步反应即可制得。实验表明,该传感器分子不但能够单一选择性、高灵敏度的识别氰根离子,还能够在识别氰根的基础上连续高灵敏性的识别铜离子,而其它阳离子对这一检测过程没有干扰。此外,氰根和铜离子的检测试纸的制备,可方便快捷的连续检测水溶液中的CN−和Cu2+。
Description
技术领域
本发明涉及一种能够连续识别CN-和Cu2+的传感器分子及其合成方法,属于化学合成技术领域和离子检测技术领域。
背景技术
众所周知,氰根离子(CN-)是一种剧毒物质,少量的CN-即可使人急性中毒甚至致死。然而,氰化物也是一种重要的化工原料,被广泛的应用于冶金、电镀等化学工艺过程中。另外,有些植物也含有氰化物,工业生产中氰化物的使用不当或生活中饮食不当都有可能造成氰化物中毒。世界卫生组织规定了在饮用水中氰根离子的浓度不得超过1.9 uM。因此,CN-的检测在生命科学和环境监测等领域有着重要的应用。
作为人体中含量第三的微量元素,铜离子在人体的许多生理过程中都扮演着重要的角色。然而在人体中铜离子浓度过高时也会带来相应的问题。例如,当人体长时间暴露在高浓度的铜离子中时就容易导致细胞中毒和肝肾受损。因此,Cu2+的检测在生命科学和环境监测等领域有着重要的应用。
在离子检测领域,比色法或荧光法由于操作简便、仪器易得等原因而成为研究的热点。常见的CN-荧光传感器根据作用方式的可分为多种类型,比如氢键作用型传感器、脱质子型传感器、亲核加成型传感器、配位作用型传感器以及基于其它机理传感器等。其中,亲核加成型传感器能通过和CN-发生加成反应而具有识别选择性高的优点。但是大多数亲核加成型传感器往往结构复杂而难与合成并且只能单一的识别氰根离子,不能进行连续识别。而Cu2+荧光传感器也存在同样的问题。
发明内容
本发明的目的是提供一种能够高选择性、高灵敏度连续识别CN-和Cu2+的传感器分子;
本发明的另一目的是提供一种上述连续识别CN-和Cu2+传感器分子的合成方法;
本发明还有一个目的,就是提供该传感器分子连续识别CN-和Cu2+的具体应用。
一、连续识别CN-和Cu2+的传感器分子
本发明的传感器分子的结构特点是含有供电子基团的喹啉环,以及能与氰根发生加成反应的碳碳双键,其命名为2-(喹啉-2-甲烯基) 丙二腈,记为ZY。其结构式如下:
二、传感器分子的合成
本发明连续识别传感器分子的合成,是以乙醇为溶剂,丙二腈和喹啉二甲醛为底物进行回流反应;回流反应的温度为45~50℃,反应时间为1.6~2h;反应完成后冷却至室温,抽滤,干燥后用乙醇重结晶,得到紫黑色针状固体即得。其合成式如下:
反应底物丙二腈和喹啉二甲醛的摩尔比为1:1~1:1.1。
合成产物经红外图谱、核磁图谱、紫外光谱、氢谱等手段得到验证。
三、传感器分子的识别实验
1、对阴离子识别性能
分别移取0.5 mL传感器分子ZY的DMSO溶液(2×10-4 mol·L-1)于一系列10 mL 比色管中,然后再分别加入F-,Cl-,Br-,I-,AcO-,H2PO4 -,HSO4 -,ClO4 -,CN-、SCN-的水溶液(0.01mol·L-1)0.5 mL,用蒸馏水稀释至5mL。此时受体浓度为2×10-5mol·L-1,阴离子浓度为受体浓度的50倍。观察传感器分子对各阴离子的响应。
结果发现,在荧光光谱中,只有CN-的加入使得ZY的DMSO溶液在464 nm处出现最大荧光发射峰(λex=358nm);在紫外灯下,只有CN-的加入使得ZY的DMSO溶液发出蓝绿色荧光,而其它阴离子的加入,ZY的DMSO溶液颜色及荧光光谱没有任何明显的变化(图1),说明该传感器分子对CN-表现出很强的专一选择性,因此可高选择性、高灵敏度的荧光识别CN-。
2、抗干扰性能检测
为了测定ZY对CN-的检测效果,我们又进行了如下抗干扰测试:取两组10mL比色管分别加入0.5mL ZY的水溶液,再分别加入0.5mL各种阴离子的水溶液(0.01mol·L1),然后用蒸馏水稀释至5mL刻度;另外一组中分别加入0.5mL CN-,在每一个比色管中分别加入0.5mL其它九种阴离子,然后用蒸馏水稀释至5mL刻度,混合均匀后进行观察。
上述溶液静置后于25℃测其荧光发射光谱。结果发现,加入九种阴离子后ZY在464nm处的荧光打开,这与CN-对受体的影响是一致的。由此可见,ZY对CN-的检测不受其它阴离子的影响(图2)
3、受体的滴定
移取2.0mL ZY的水溶液(2.0×10-5mol/L)于石英池中,用累积加样法逐渐加入CN- 的水的溶液。于25℃测其荧光发射光谱(图3)。滴定实验说明ZY的荧光强度受到氰根浓度的影响,伴随着氰根浓度的增加而增强。由此说明,化合物ZY在纯水体系中能单一选择性荧光识别氰根离子,而且对CN-的检测灵敏度很高。
4、对CN-最低检测限的测定
根据荧光滴定实验,得到了荧光强度与氰根浓度的线性关系,继而得到线性方程。再利用线性方程的系数和最低检测线的公式计算最低检测线。该受体对CN-的检测灵敏度很高,达到了5.09×108mol/L(0.05 μM),远低于世界卫生组织(WHO)规定的正常饮用水中CN-的含量标准(<1.9μM)。
5、对阳离子识别性能
分别移取0.5 mL受体ZY的水溶液(2×10-4 mol·L-1)于一系列10 mL 比色管中,分别加入0.5 mL CN形成络合物ZY-CN,然后再分别加入Fe3+,Hg2+,Ag+,Ca2+,Cu2+,Co2+,Ni2+,Cd2+,Pb2+,Zn2+,Cr3+,Mg2+的水溶液(0.004 mol·L-1)0.5 mL。用蒸馏水稀释至5mL,此时受体浓度为2×10-5mol·L-1,阳离子浓度为受体浓度的20倍,观察受体ZY对各阳离子的响应。
发现,在紫外灯下,只有Cu2+的加入使得络合物ZY-CN溶液的蓝绿色荧光完全猝灭。在相应的荧光光谱上,只有Cu2+使得发射波长在464nm处的荧光消失,而其它阳离子对ZY-CN溶液的荧光几乎没有影响。说明ZY-CN在DMSO中能够高选择性单一检测Cu2+。
6、对铜离子的滴定
移取2.0mLZY-CN的水溶液(2.0×10-5mol/L)于石英池中,用累积加样法逐渐加入Cu2+ 的水溶液,于25℃测其荧光发射光谱(图6)。滴定实验说明ZY-CN的荧光强度受到铜离子浓度的影响,伴随着铜离子浓度的增加而减弱。说明,化合物ZY-CN在水溶液体系中仍然能单一选择性荧光识别铜离子,而且对铜离子的检测灵敏度很高,因此,ZY-CN在铜离子检测方面有潜在的应用价值。
7、对Cu2+最低检测限的测定
根据荧光滴定实验,得到了荧光强度与铜离子浓度的线性关系,继而得到线性方程。再利用线性方程的系数和最低检测线的公式计算最低检测线。该受体对铜离子的检测灵敏度很高,达到了1.23×108mol/L。
四、CN-和Cu2+离子试纸的制作
将处理过的滤纸在传感器分子ZY水溶液(2×10-4 mol·L1)中浸润10分钟左右,使传感器分子ZY充分负载于滤纸上,取出晾干。该滤纸荧光灯照射下没有荧光。
将上述滤纸分别浸润于F-,Cl-,Br-,I-,AcO-,H2PO4 -,HSO4 -,ClO4 -,CN-、SCN-的水溶液中,发现只有浸润在CN-水溶液中的滤纸在荧光灯照射下发出了蓝绿色的荧光,而浸润在其它阴离子水溶液中的滤纸在荧光灯照射下的荧光没有发生变化。
将在CN-水溶液中浸润的滤纸晾干后继续浸入含有Cu2+的溶液,在荧光灯照射下滤纸的蓝绿色的荧光又消失了。这种鲜明的颜色对比也说明了该受体对CN- 和Cu2+离子有着高度的荧光识别能力。
五、传感器分子对CN-和Cu2+的识别机理
针对传感器分子ZY对CN-和Cu2+识别机理的探究,我们通过核磁滴定、高分辨质谱等表征手段进行了验证。核磁滴定谱图表明:8.75ppm 处Ha的信号峰随CN-离子的加入随即消失,与此同时在δ=5.61处出现了一个新的信号峰Hb,这就说明氰根的亲核加成发生在探针ZY芳环上缺电子的部位。高分辨质谱对主体与离子的配合物数据表明:231.0488处的出峰和一分子受体与CN-离子发生亲核加成后的分子量一致。另外,向发生亲核加成的溶液中加入铜离子后得到的高分辨质谱数据表明:526.1227是两分子氰根加成产物ZY-CN与一分子铜离子络合后得到的峰。因此,受体ZY对CN-和Cu2+的识别机理探讨如下:当加入CN-时,CN-对探针ZY的“C=C”发生亲核加成,形成一个带负电荷稳定的中间体,向该中间体继续加入Cu2+后就会发生一个络合反应, ZY-CN与铜离子络合,使得受体的荧光恢复原状(图6)。
综上所述,本发明设计合成的传感器分子ZY(2-(喹啉-2-甲烯基) 丙二腈)结构简单,合成方法简便,只需一步反应的即可制得。更为重要的是,该传感器分子不但能够单一选择性、高灵敏度的识别氰根离子,还能够在识别氰根的基础上连续高灵敏性的识别铜离子,而其它阳离子对这一检测过程没有干扰。此外,氰根和铜离子的检测试纸的制备,可方便快捷的连续检测水溶液中的CN和Cu2+。
附图说明
图1为ZY以及其加入50倍的阴离子时的荧光光谱(激发波长:358nm,发射波长464nm)。
图2为ZY对氰根离子识别的抗干扰性能。
图3为不同浓度的CN- (0-45 倍) 存在下受体ZY的荧光光谱。
图4为ZY+CN-以及其加入20倍的阳离子时的荧光光谱(激发波长:358nm,发射波长:464nm)。
图5为不同浓度的Cu2+ (0-1.9倍) 存在下受体ZY-CN的荧光光谱。
图6为ZY对CN-和Cu2+的识别机理图。
具体实施方式
下面通过具体实施例对本发明传感器分子的结构、合成及应用作进一步说明。
1、传感器分子的合成及表征
将4mmol 丙二腈和4mmol 喹啉二甲醛置于100 mL圆底烧瓶中,加入25mL 乙醇,在油浴上50℃加热反应2h,待反应停止冷却至室温后,抽滤;所得固体在真空干燥箱中烘干,然后用乙醇重结晶,得到紫黑色针状固体即为传感器分子,记为ZY。产率: 81.7%。产物的表征数据如下:
ZY: m.p: 168-170 °C; 1H NMR (400 MHz, CDCl3) δ 8.34 (d, J = 8.2 Hz,1H), 8.24 (d, J = 7.9 Hz, 1H), 7.99 (s, 1H), 7.90 (d, J = 8.3 Hz, 1H), 7.85(s, 1H), 7.77 (d, J = 8.4 Hz, 1H), 7.72 (d, J = 6.9 Hz, 1H); 13C NMR (150 MHz,CDCl3) δ 157.67, 148.52, 148.34, 137.72, 131.33, 130.67, 129.91, 129.29,127.80, 122.33, 113.85, 112.31, 87.93; ESI-MS m/z: (M+H)+ Calcd for C13H7N3206.0640; Found 206.1000; Anal. Calcd for C13H7N3: C, 76.08; H, 3.44; N,20.48; Found C 76.27; H, 3.12; N, 20.61。
2、CN-、Cu2+的溶液检测
CN-的检测:移取传感器分子的DMSO溶液(2×10-4 mol·L-1)于一系列10 mL 比色管中,分别加入F-,Cl-,Br-,I-,AcO-,H2PO4 -,HSO4 -,ClO4 -,CN-、SCN-的水溶液(0.01 mol·L-1)0.5 mL,若溶液发出蓝绿色荧光,则说明加入的是CN-;若溶液的荧光颜色不发生变化,说明加入的是其它阴离子。
Cu2+的检测:移取传感器分子的DMSO溶液(2×10-4 mol·L-1)于一系列10 mL 比色管中,先分别加入 CN,溶液发出蓝绿色荧光;再向其中分别加入Fe3+,Hg2+,Ag+,Ca2+,Cu2+,Co2+,Ni2+,Cd2+,Pb2+,Zn2+,Cr3+,Mg2+的水溶液;若溶液的蓝绿色荧光完全猝灭,则说明加入的是Cu2+;若络合物溶液的蓝绿色荧光不发生变化,则说明加入的不是Cu2+。
3、CN-、Cu2+的试纸检测
检测试纸的制备:将传感器分子ZY配制成2×10-4 mol·L1的水溶液;将处理过的滤纸剪成长约3cm,宽约3cm的正方形,浸润在ZY水溶液中10分钟左右,取出晾干,得到检测试纸。该试纸荧光灯照射下没有荧光。
CN-的检测:将滤纸分别浸润于F-,Cl-,Br-,I-,AcO-,H2PO4 -,HSO4 -,ClO4 -,CN-、SCN-的水溶液中,若滤纸在荧光灯照射下发出蓝绿色的荧光,则说明浸润的是CN-溶液;若滤纸在荧光灯照射下荧光没有发生变化,则说明浸润的是其它阴离子溶液。
Cu2+的检测:将滤纸先在CN-水溶液(0.01 mol·L-1)中浸润、晾干后继续浸入Fe3+,Hg2+,Ag+,Ca2+,Cu2+,Co2+,Ni2+,Cd2+,Pb2+,Zn2+,Cr3+,Mg2+的水溶液中(0.004 mol·L-1),若滤纸在荧光灯照射下的蓝绿色荧光完全猝灭,则说明浸润的是Cu2+溶液;若滤纸在荧光灯照射下的蓝绿色荧光不发生变化,则说明浸润的是其它阳离子。
Claims (5)
1.一种能够连续识别CN-和Cu2+的传感器分子在检测CN-中的应用,其特征在于:在传感器分子的DMSO溶液中,分别加入F-,Cl-,Br-,I-,AcO-,H2PO4 -,HSO4 -,ClO4 -,CN-、SCN-的水溶液,只有CN-的加入使溶液发出蓝绿色荧光,而其它阴离子的加入不能使溶液颜色发生变化;传感器分子,其结构式为:
。
2.一种能够连续识别CN-和Cu2+的传感器分子在检测Cu2+中的应用,其特征在于:在传感器分子的DMSO溶液中,先加入 CN-形成传感器分子-CN-络合物的溶液,再分别加入Fe3+,Hg2 +,Ag+,Ca2+,Cu2+,Co2+,Ni2+,Cd2+,Pb2+,Zn2+,Cr3+,Mg2+的水溶液;若络合物溶液的蓝绿色荧光完全猝灭,则说明加入的是Cu2+;若络合物溶液的蓝绿色荧光不发生变化,则说明加入的不是Cu2+;传感器分子,其结构式为:
。
3.负载有如权利要求1所述能够连续识别CN-和Cu2+的传感器分子的试纸。
4.如权利要求3所述负载有能够连续识别CN-和Cu2+的传感器分子的试纸的应用,其特征在于:将滤纸分别浸润于F-,Cl-,Br-,I-,AcO-,H2PO4 -,HSO4 -,ClO4 -,CN-、SCN-的水溶液中,若滤纸在荧光灯照射下发出蓝绿色的荧光,则说明浸润的是CN-溶液;若滤纸在荧光灯照射下荧光没有发生变化,则说明浸润的不是CN-溶液。
5.如权利要求3所述负载有能够连续识别CN-和Cu2+的传感器分子的试纸的应用,其特征在于:将滤纸先在CN-水溶液中浸润、晾干后继续浸入Fe3+,Hg2+,Ag+,Ca2+,Cu2+,Co2+,Ni2+,Cd2+,Pb2+,Zn2+,Cr3+,Mg2+的水溶液中,若滤纸在荧光灯照射下的蓝绿色荧光完全猝灭,则说明浸润的是Cu2+溶液;若滤纸在荧光灯照射下的蓝绿色荧光不发生变化,则说明浸润的是其它阳离子。
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