CN110498794B - 咪唑并[1,2-a]吡啶衍生物类Pd2+荧光探针及其应用 - Google Patents
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract
本发明公开了一种咪唑并[1,2‑a]吡啶衍生物类Pd2+荧光探针，其化学结构式如式（1）所示。本发明的荧光探针在PBS溶液(pH=7.40)中对Pd2+有独特的荧光选择性、较高的灵敏度及较强的抗其它离子干扰能力，具有巨大的应用前景。
Description
技术领域
本发明涉及有机小分子荧光探针领域，尤其涉及一种咪唑并[1,2-a]吡啶衍生物类Pd2+荧光探针的合成及其应用。
背景技术
钯的产量很少,属于贵金属,但拥有广泛的用途,在化学中, 钯主要作为催化剂应用于大量反应中,同时钯也用于制造手表、外科器具和牙科材料等。钯元素被广泛应用的同时,对环境也产生了巨大的污染。人类在生活中接触的钯主要是由于汽车尾气净化处理装置造成的,在尾气净化处理装置中, 钯与铂、锗作为催化剂的活性成分来净化汽车尾气中的有害物质,但在净化过程中,由于高温、化学反应、机械摩擦等原因而使铂、钯、锗以颗粒物的形式随净化后的尾气排放到环境中,并在一定条件下转化为卤化物,通过空气、水和土壤进入生物链,对人体的健康产生潜在的损害。钯及其化合物经口摄人吸收很少,吸入的钯化合物主要滞留于肺部,吸收后的钯很快转运至肝、肾、脾、肾上腺、肺、骨骼等器官,会与人体中大分子物质,比如,维生素,蛋白质发生络合效应,从而抑制细胞的正常功能。因此,定量检测钯离子的含量对维持人体正常生命活动有着重要的意义。
目前用于检测钯离子方法主要有电感藕合等离子体质谱法、等离子体发射光谱法、原子吸收光谱法、固相微萃取-高效液相色谱法和荧光光谱法。但这些方法耗时长,响应慢,工艺复杂,而荧光光谱法能很好地克服这些缺点,所以需要研发高选择性检测钯离子的荧光探针。
发明内容
针对现有技术的不足，本发明解决的问题是提供一种咪唑并[1,2-a]吡啶衍生物类Pd2+荧光探针及其应用。
本发明的技术方案是：一种咪唑并[1,2-a]吡啶衍生物类Pd2+荧光探针，其化学结构式如式（1）所示：
本发明还包括咪唑并[1,2-a]吡啶衍生物类Pd2+荧光探针的应用，式（1）化合物在PBS溶液(pH=7.40)中对Pd2+有独特的荧光选择性。
本发明还包括咪唑并[1,2-a]吡啶衍生物类Pd2+荧光探针的合成方法，在乙腈溶液中，将2-（4-咪唑并[1,2-a]吡啶基）苯酚、溴丙炔与碳酸钾按照摩尔比1:1.2:1.5投料，加热回流12小时，得到咪唑并[1,2-a]吡啶衍生物类Pd2+荧光探针。
配制咪唑并[1,2-a]吡啶衍生物类Pd2+荧光探针的PBS溶液(pH=7.40)，分别加入定量的LiCl，NaCl，KCl，CsCl，MgCl2·6H2O，CaCl2·6H2O， AlCl3·6H2O，Pb（NO3）2，CrCl3·6H2O, MnCl2·4H2O, FeCl3·6H2O, FeCl2·4H2O, CoCl2·6H2O, NiCl2·6H2O，HgCl2，C4H6O4Zn·2H2O，SrCl2·6H2O，CuCl2·2H2O, CdCl2·2½H2O, AgNO3的水溶液，通过荧光光谱测试来研究对不同金属离子的选择性，测其荧光发射波谱强度变化发现：本发明所述咪唑并[1,2-a]吡啶衍生物类Pd2+荧光探针即式（1）化合物对Pd2+有独特的荧光选择性，如图1所示。逐渐加入Pd2+至30当量后，化合物1在378处荧光强度明显降低，如图2所示。因此，咪唑并[1,2-a]吡啶衍生物即式（1）化合物作为Pd2+荧光探针具有巨大的应用。
附图说明
图1：式（1）化合物（10-7M）的PBS溶液(pH=7.40)中加入30当量的不同金属离子后的荧光强度变化图，图1中FL Intensity为荧光强度，Wavelength为波长。
图2：式（1）化合物（10-7M）的PBS溶液(pH=7.40)中进行Pd2+荧光滴定图。图中FLIntensity为荧光强度，Wavelength为波长，equiv为倍数。
图3：式（1）化合物（10-7M）和30当量的Pd2+共存的PBS溶液(pH=7.40)中加入30当量的其它金属离子后荧光强度的变化柱状图, 图中FL Intensity为荧光强度。
图4是式（1）化合物合成方法反应式图。
具体实施方式
实施例1：式（1）化合物的合成方案如下式所示：
具体合成步骤如下：
在50 mL圆底烧瓶中依次加入0.5g（2.38 mmol）2-（4-咪唑并[1,2-a]吡啶基）苯酚，0.34g（2.856mmol）溴丙炔，0.5g碳酸钾，30 mL乙腈，加热回流12小时。TLC检测反应完成后，加入100 mL二氯甲烷，30 mL水洗三次，二氯甲烷层硫酸钠干燥，浓缩，柱层析得0.34g白色固体，产率57.6%。
核磁共振氢谱测定：1H NMR（400 MHz，CDCl3）：δ8.43 (m， 1H),8.24 (s, 1H),8.13 (d, 1H), 7.62 (d, 1H),7.30 (m, 2H),7.15 (t, 2H), 7.09 (d, 1H), 6.76 (d,1H), 4.87 (d, 2H)。
实施例2：
向式（1）化合物（10-7M）的PBS溶液中分别加入30当量的Pd2+， Ag+， Al3+， Ca2+，Cd2+， Co2+， Cr3+， Cs+， Cu2+， Fe2+， Fe3+， K+， Li+， Mg2+， Mn2+， Na+， Ni2+， Pb2+， Sr2+和Zn2+后，测其378nm处荧光发射强度变化发现：式（1）化合物对Pd2+有独特的荧光选择性，加入30当量的Pd2+后，化合物1在378nm处荧光强度明显降低，如图1,2所示。
实施例3：
于式（1）化合物（10-7M）和30当量的Pd2+的PBS溶液中分别加入等当量的Ag+， Al3+，Ca2+， Cd2+， Co2+， Cr3+，Cs+， Cu2+， Fe2+， Fe3+， K+， Li+， Mg2+， Mn2+， Na+， Ni2+， Pb2+，Sr2+和 Zn2+后，测其在378nm荧光发射强度变化发现：式（1）化合物对其它离子有较强的抗干扰能力，如图3所示。
Claims (2)
1.一种咪唑并[1,2-a]吡啶衍生物类Pd2+荧光探针，其特征在于：它是 2-(2-(炔丙氧基)苯基)咪唑并[1,2-a]吡啶，其化学结构式如式(1)所示:
(1)
式(1)化合物在pH=7.40的PBS溶液中，对Pd2+有荧光选择性。
2.权利要求 1 所述咪唑并[1,2-a]吡啶衍生物类Pd2+荧光探针的合成方法，其特征在于：在乙腈溶液中，将 2-(4-咪唑并[1,2-a]吡啶基)苯酚、溴丙炔与碳酸钾按照摩尔比 1:1.2:1.5 投料，加热回流 12 小时，得到咪唑并[1,2-a]吡啶衍生物类 Pd2+荧光探针。
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