CN113666912B - 一种可用于检测水溶液中银离子的荧光传感器及其制备方法 - Google Patents
一种可用于检测水溶液中银离子的荧光传感器及其制备方法 Download PDFInfo
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- 229910052709 silver Inorganic materials 0.000 title claims abstract description 14
- 239000004332 silver Substances 0.000 title claims abstract description 14
- -1 silver ions Chemical class 0.000 title claims abstract description 11
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- 238000002360 preparation method Methods 0.000 title abstract description 7
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims abstract description 6
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- 239000000126 substance Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 18
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- 229940125904 compound 1 Drugs 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 claims description 3
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- QWFHFNGMCPMOCD-UHFFFAOYSA-N 6-bromopyridine-2-carbaldehyde Chemical compound BrC1=CC=CC(C=O)=N1 QWFHFNGMCPMOCD-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
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- 102000004190 Enzymes Human genes 0.000 description 1
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- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
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- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
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- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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Abstract
本发明公开一种可用于检测水溶液中银离子的具有完美对称结构、含咪唑骨架荧光传感器及其制备方法，化学结构式为：所述的含咪唑骨架的荧光传感器是通过邻苯二胺与6‑卤代吡啶‑2‑甲醛反应生成苯并咪唑环，通过与1‑卤代正己烷反应引入脂肪烃长链，最后通过Suzuki偶联反应，合成了一种具有完美对称结构、含咪唑骨架的荧光传感器。本发明的荧光传感器对真实水样中的Ag+具有高的选择性和灵敏度，以及较低的检出限。可应用于纸色谱中定性检测水样中的Ag+,检出限低于WHO规定的饮用水水平，应用前景广泛。
Description
技术领域
本发明涉及有机小分子荧光传感器领域，尤其涉及一种可用于检测水溶液中银离子具有完美对称结构、含咪唑骨架荧光传感器及其制备方法。
背景技术
银离子(Ag+)因其优异的抗菌性和稳定性而引起了人们的极大关注，银离子广泛用于化妆品、纺织品、空调以及洗衣机等日用品中的抗菌剂。每年有大量的银离子从工业中释放到环境中，当银释放到环境中时，主要的环境问题是银的生物累积和银氧化成银离子。银离子对细菌、藻类以及浮游生物在内的多种生物都有剧毒。银离子一旦进入人体后会在人体内积累，银离子在人体内通过破坏代谢酶等许多生物分子的活性而引起一系列疾病，如刺激皮肤、引起胃部不适、造成神经损伤、引起银中毒、甚至会造成器官水肿和死亡。因此，有必要制备一种灵敏度高、检出限低的传感器来检测Ag+。在众多检测中，荧光检测技术简单快速且广泛被应用，这使得开发一种高效的荧光传感器用于实际水样的实时监测成为了可能。
发明内容
为此，本发明提供了一种具有完美对称结构、含咪唑骨架的荧光传感器。
本发明用于水溶液中Ag+检测的具有完美对称结构、含咪唑骨架的荧光传感器，其化学结构如下：
本发明提供一种用于水溶液中Ag+检测的具有完美对称结构、含咪唑骨架的荧光传感器的合成路线如下：
所述合成步骤包括以下三步：
第一步：以邻苯二胺与6-卤代吡啶-2-甲醛为原料，所述邻苯二胺与6-卤代吡啶-2-甲醛发生缩合反应，生成2-(6-卤代吡啶-2-基)-1H-苯并咪唑(即化合物1)。
第二步：将2-(6-卤代吡啶-2-基)-1H-苯并咪唑(即化合物1)与1-卤代正己烷发生反应，生成2-(6-卤代吡啶-2-基)-1-正己基-1H-苯并咪唑(即化合物2)。
第三步：将2-(6-卤代吡啶-2-基)-1-己基-1H-苯并咪唑(即化合物2)与双(频哪醇合)二硼在钯催化剂催化下生成1-正己基-2-(6-(4,4,5,5-四甲基-1,3,2-二氧硼烷-2-基吡啶-2-基)-1H-苯并咪唑(即化合物3)，最后与2-(6-卤代吡啶-2-基)-1-己基-1H-苯并咪唑(即化合物2)在钯催化剂催化下发生偶联反应，得到含咪唑骨架的荧光传感器(即化合物4)。
本发明通过设计合成具有完美对称结构、含咪唑骨架的荧光传感器，并成功用于水溶液中Ag+检测，该荧光传感器具有高的选择性和高的灵敏度，而且具有较低的检出限(45.91nM)。
附图说明
图1：化合物(4)10μM的DMF-HEPES溶液(9：1，v/v,pH 7.4)中加入不同浓度的Ag+(0-20μM)的紫外吸收图；
图2：化合物(4)10μM的DMF-HEPES溶液(9：1，v/v,pH 7.4)中不同金属阳离子的荧光强度变化比例柱状图；
图3：化合物(4)10μM的DMF-HEPES溶液(9：1，v/v,pH 7.4)中进行Ag+标准品溶液的荧光滴定图。
具体实施方式
以下实施例中所涉及的试剂未特别说明，则为商业化产品，纯度为分析纯。为了更加清楚的解释本发明所解决的技术问题及技术方案，以下所述的具体实施例对本发明进行了进一步详细说明。此处所述的具体实施例仅用于解释本发明，并不用于限定本发明。
实施例1
化合物1的制备
在50mL圆底烧瓶中，加入0.60g邻苯二胺，0.93mL 6-溴吡啶-2-甲醛和20mL无水乙醇，室温搅拌3h，旋干溶剂，以石油醚/乙酸乙酯为洗脱剂进行硅胶柱层析纯化，得0.89g白色固体(即化合物1)，收率65％。
HRMS(ESI)m/z calcd.for C12H8BrN3([M+H]+):273.9974 and 275.9954；found:274.0022 and 275.9995.
化合物2的制备
在50mL圆底烧瓶中，加入0.78g碳酸铯，0.55g化合物1和20mL四氢呋喃，加入516μL1-溴代正己烷，60℃搅拌反应3天。反应结束后冷却至室温，过滤，洗涤，收集并旋干溶剂，以石油醚/乙酸乙酯为洗脱剂进行硅胶柱层析纯化，得0.33g白色固体(化合物2)收率：50.1％。
HRMS(ESI)m/z calcd.for C18H20BrN3([M+H]+):358.0919 and 360.0890；found:358.0889 and 360.0870.
化合物4的制备
氮气保护下，在50mL圆底烧瓶中，加入0.14g化合物2,0.13g双(频哪醇合)二硼，0.13g乙酸钾，0.02g[1,1’-双(二苯基膦)二茂铁]二氯化钯二氯甲烷络合物和15mL DMSO，90℃搅拌反应24h，反应结束后降温至室温，倾入50mL水中，加入50mL乙酸乙酯，硅藻土过滤，洗涤，分液，饱和食盐水洗涤，干燥，过滤，旋干，得黑色油状液体。
氮气保护下，在50mL圆底烧瓶中，加入黑色油状液体,0.02g反-二氯化双(三苯基膦基)钯(II)，0.18g无水碳酸钾，0.14g化合物2，6mL DMF和3mL水，120℃反应8h，反应结束后降温至室温，倾入50mL水中，加入50mL乙酸乙酯，硅藻土过滤，洗涤，分液，饱和食盐水洗涤，干燥，过滤，旋干，石油醚/乙酸乙酯为洗脱剂进行硅胶柱层析纯化，得0.10g白色固体(即化合物IS)，收率46.2％。
HRMS(ESI)m/z calcd.for C36H40N6([M+H]+):557.3357；found:557.2852.
实例2
在10μM化合物4的DMF-HEPES溶液(9：1，v/v，pH 7.4)中分别加入Ag+(0-20μM)，测其紫外吸收变化；发现化合物4的紫外吸收峰发生明显的蓝移(紫外吸收峰从322nm迁移到310nm处)；同时，随着Ag+的加入紫外吸收峰带明显下降。如图1所示。
在10μM化合物4的DMF-HEPES溶液(9：1，v/v，pH 7.4)中分别加入2当量的不同金属阳离子溶液，测其在394nm荧光发射强度变化；发现在加入2当量不同金属阳离子溶液后，化合物4对Ag+具有良好的选择性，当在以上溶液中再加入2当量的Ag+后，传感器可排除干扰，正常检测水溶液中的Ag+，如图2所示。
在10μM化合物4的DMF-HEPES溶液(9：1，v/v，pH 7.4)中加入不同浓度Ag+溶液进行荧光滴定实验，对比发现，化合物4作为识别Ag+的荧光传感器具有现实可行性，如图3所示。
以上所述仅为本发明优选实施例，并不用于限制本发明，凡在本发明的原则和精神之内所作的任何改动，等同替换和改进等，均包含在本发明的保护范围之内。
Claims (2)
1.一种可用于检测水溶液中银离子的荧光传感器，其特征在于，该荧光传感器的化学结构式如下：
2.根据权利要求1所述的荧光传感器的合成方法，其特征在于，其合成步骤包括以下三步：
第一步：以邻苯二胺与6-卤代吡啶-2-甲醛为原料，所述邻苯二胺与6-卤代吡啶-2-甲醛发生缩合反应，生成化合物1X为卤素；
第二步：将化合物1与1-卤代正己烷发生反应，生成化合物2X为卤素；
第三步：将化合物2与双(频哪醇合)二硼在钯催化剂催化下生成化合物3最后化合物2与化合物3在钯催化剂催化下发生偶联反应，得到化合物4/>
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