CN111205330B - 一类双磷光发射探针及其制备方法 - Google Patents
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Abstract
本发明公开了一类双磷光发射探针及其制备方法,利用二(2‑吡啶甲基)胺结构对金属离子的响应以及双磷光发射铱配合物对氧气的响应,构建了一类既能检测氧气又能检测金属离子的双发射探针。相对于现有技术中公开的单磷光发射铱配合物探针而言,本发明为单个探针对多个检测目标的同时检测提供了新的思路;且本发明公开的双磷光发射铱配合物的制备过程简单,反应条件温和,可操作性强。
Description
技术领域
本发明属于有机光电材料技术领域。具体涉及一类双磷光发射探针及其制备方法。
背景技术
磷光铱配合物因其具有长的发光寿命、发光波长易调节等优异的光物理性质而被广泛的应用于传感领域。以此为基础的发光探针的研究更是受到了广泛的关注。相关研究发现,现有技术中的铱配合物传感探针大多属于单波长发射探针,当探针与分析物作用时,主要依靠发射强度的变化来检测物质,虽然发射峰的位置可能会发生一些微小的变化,但是探针的发射谱的特征基本保持一致。这种传统的利用单一波长强度的变化来反应分析物或者分析环境的变化的灰度传感容易受外界环境(如分析物浓度,温度等)或者自身变量(如探针浓度等)的影响。
为此,相关领域工作人员开始研究可有效解决该问题的双波长发射的磷光探针,已报道的双波长发射的磷光铱配合物探针大多是由两种或多种铱配合物组合而成,如利用两种对分析物有不同响应的的铱配合物组合成纳米粒子,或者混杂两种磷光探针从而达到双波长发光的目的,但是这些方法存在一些问题:如合成步骤复杂、细胞吸收效率低以及检测的精度低等。且现有的检测金属离子的磷光探针大都是通过发射光谱的磷光强度的变化实现感知的,检测过程易受到氧气的影响。
发明内容
本发明的目的在于解决现有技术中的不足,提供一类双磷光发射探针及其制备方法,为实现单个探针对多个检测目标的同时检测提供了新的思路。
本发明的技术方案为:本发明公开的一类双磷光发射探针,结构通式如下:
其中,C^N配体为下列中的任一个:
N^N配体为下列中任一个:
其中,n=0、1、2、3…。
所述双磷光发射探针可在对氧气有响应的同时对金属离子也有响应,由405nm激光器激发,发射光谱上有两个发射峰,高能量带的发射峰在480-520nm左右,对氧气有响应,低能量带的发射峰在600-650nm左右,对金属离子有响应。
进一步地,该类探针的合成路线类似,以分子式如下的一种双磷光发射探针为例对其具体合成路线和合成步骤进行描述:
具体合成步骤是:
1)化合物1的合成
称取联吡啶和二氧化硒于双口瓶中,加入溶剂1,4-二氧六环,在102℃下反应24h;反应结束后,趁热抽滤,旋干;柱层析分离得到化合物1;
2)化合物2的合成
将化合物1溶于乙醇中,再将硝酸银溶于水中;将两种溶液加入单口烧瓶中混合搅拌,开始滴加1.0M的氢氧化钠溶液,直到溶液变成深黑为止,反应15h;抽滤除去固体,旋干乙醇,盐酸调pH至3.5,抽滤得白色固体化合物2;
3)化合物3的合成
在圆底烧瓶中加入乙二胺和乙醇,在冰水浴中,二碳酸二叔丁酯溶解于乙醇中,加入饱和氯化钠溶液至有白色沉淀析出,过滤除去固体,滤液用二氯甲烷萃取,无水硫酸钠干燥,旋干得淡黄色油状液体化合物3;
4)化合物4的合成
称取化合物3、碳酸钾和2-(氯甲基吡啶氢溴酸盐)于双口瓶中,密封,抽真空,氮气保护,在80℃下反应24h;反应结束后,旋干;柱层析分离得到化合物4;
5)化合物5的合成
在圆底烧瓶中加入三氟乙酸,将化合物4溶解于二氯甲烷中,在0℃冰浴的条件下,滴加到三氟乙酸中,室温搅拌过夜;旋干溶剂;加入100mL、2M的氢氧化钠溶液中,用二氯甲烷萃取旋干得化合物5;
6)化合物6的合成
称取化合物2、NHS和EDC于双口瓶中,抽真空,氮气保护,在25℃下反应12h;打入三乙胺和溶于DMF的化合物5,在25℃下反应24h;旋干DMF;柱层析分离得到化合物6;
7)化合物7的合成
分别称取化合物6和二氯桥加入圆底烧瓶中,抽真空,鼓氮气;在氮气氛围下,注射二氯甲烷和甲醇的的混合溶液,搅拌使其溶解;50℃下反应4h后,待粗产品冷却至室温,加入六氟磷酸钾,在室温下搅拌2h后;将粗产品减压蒸馏除去溶剂,将产物在硅胶柱中用柱层析分离法分离得到铱配合物。
本发明的有益效果是:
1.本发明利用二(2-吡啶甲基)胺结构对金属离子的响应以及双磷光发射铱配合物对氧气的响应,构建了一类既能精确检测氧气又能精确检测金属离子的探针,相对于现有技术中公开的单磷光发射铱配合物探针而言,为单个探针对多个检测目标的同时检测提供了新的思路;
2.本发明公开的双磷光发射铱配合物的制备过程简单,反应条件温和,可操作性强,易于大规模制备使用。
附图说明
图1为实施例2获得的双磷光发射铱配合物的氧气滴定发射光谱图;
图2为实施例2获得的双磷光发射铱配合物的铜离子滴定发射光谱图。
具体实施方式
以下实施例进一步说明本发明的内容,但不应理解为对本发明的限制。在不背离本发明实质的情况下,对本发明方法、步骤或条件所作的修改和替换,均属于本发明的范围。
实施例1:一种双磷光发射铱配合物的制备
本实施例中以下述结构的铱配合物分子的制备为例进行描述:
该铱配合物的具体合成路线为:
具体的合成步骤为:
1)化合物1的合成
称取联吡啶(6.0mmol,1.1g)和二氧化硒(18mmol,2.0g)于双口瓶中,加入溶剂1,4-二氧六环,在102℃下反应24h;反应结束后,趁热抽滤,旋干;柱层析分离,极性为二氯甲烷:甲醇(200:1→150:1),得到化合物1;
2)化合物2的合成
将化合物1(10mmol,2.0g)溶于乙醇中,再将硝酸银(12.6mmol,1.4g)溶于水中;将两种溶液加入单口烧瓶中混合搅拌,开始滴加1.0M的氢氧化钠溶液,直到溶液变成深黑为止,反应15h;抽滤除去固体,旋干乙醇;盐酸调pH至3.5,抽滤得白色固体化合物2;于真空干燥箱里面烘干后得到产物;
3)化合物3的合成
在圆底烧瓶中加入乙二胺(33.3mmol,2.0g)和乙醇,在冰水浴中,二碳酸二叔丁酯(6.7mmol,1.5g)溶解于乙醇中,加入饱和氯化钠溶液至有白色沉淀析出,过滤除去固体,滤液用二氯甲烷萃取,无水硫酸钠干燥,旋干得淡黄色油状液体化合物3;
4)化合物4的合成
称取化合物3(2.0mmol,320mg)、碳酸钾(8mmol,1.1g)和2-(氯甲基吡啶氢溴酸盐)(16mmol,1.84g)于双口瓶中,密封,抽真空,氮气保护,在80℃下反应24h;反应结束后,旋干;柱层析分离得到化合物4;
5)化合物5的合成
在圆底烧瓶中加入三氟乙酸10mL,将化合物4溶解于40mL的二氯甲烷中,在0℃冰浴的条件下,滴加到三氟乙酸中,室温搅拌过夜;旋干溶剂;加入100mL、2M的氢氧化钠溶液中,用二氯甲烷萃取旋干得化合物5;
6)化合物6的合成
称取化合物2(2mmol,428mg)、NHS(4mmol,460mg)和EDC(4mmol,768mg)于双口瓶中,抽真空,氮气保护,在25℃下反应12h;打入三乙胺和溶于DMF的化合物5(2mmol,484mg),在25℃下反反应24h;旋干DMF;柱层析分离得到化合物6;
7)化合物7的合成
分别称取化合物6(mmol,439mg)和二氯桥(0.5mmol,706mg)加入圆底烧瓶中,抽真空,鼓氮气;在氮气氛围下,注射30mL的二氯甲烷和甲醇的的混合溶液(2:1,v/v),搅拌使其溶解;50℃下反应4h后,待粗产品冷却至室温,加入六氟磷酸钾,在室温下搅拌2h后;将粗产品减压蒸馏除去溶剂,将产物在硅胶柱中用柱层析分离法分离得到铱配合物。
实施例2:磷光铱配合物的响应测试
(1)配合物的氧气滴定的发射光谱测试条件:磷光铱配合物浓度为1×10-5mol/L,溶剂为体积比为1:9的甲醇-水溶液,氧气的测试浓度依次是0%,4%,8%,12%,16%,20%,60%,80%,100%。
(2)配合物的铜离子滴定的发射光谱测试条件:磷光铱配合物浓度为1×10-5mol/L,溶剂为体积比为1:9的甲醇-水溶液,体积为2mL,加入浓度为8×10-4mol/L的铜离子溶液,铜离子的测试体积依次是0μL,5μL,10μL,15μL,20μL,25μL,30μL,35μL,40μL,45μL,50μL。
氧气滴定光谱图如图1所示,从图中可以看出有两个发射峰,且随着氧气浓度的增大,两个发射峰的发射波长基本不变,而480-520nm左右的峰发射强度逐渐增强,由此可以推断,该配合物对氧气有响应。
铜离子滴定光谱图如图2所示,从图中可以看出有两个发射峰,且随着铜离子浓度的增大,两个发射峰的发射波长基本不变,而600-650nm左右的峰的发射强度逐渐增强,由此可以推断,该配合物对铜离子有响应。
由此可见,此材料在对氧气有响应的同时也对铜离子有响应,从而为单个探针对多个检测目标的同时检测提供了新的思路
以上显示和描述了本发明的基本原理、主要特征及优点。但是以上所述仅为本发明的具体实施例,本发明的技术特征并不局限于此,任何本领域的技术人员在不脱离本发明的技术方案下得出的其他实施方式均应涵盖在本发明的专利范围之中。
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