CN108821998B - 基于聚集诱导发光的铀酰离子检测的有机荧光分子 - Google Patents
基于聚集诱导发光的铀酰离子检测的有机荧光分子 Download PDFInfo
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Abstract
本发明公开了一种检测限、检测范围和选择性方面兼优兼顾的有机荧光分子,该有机荧光分子是利用四苯基乙烯(TPE)基团和识别基团,通过化学修饰合成本发明的新型聚集诱导发光(AIE)型有机荧光分子,其中,所述发光基团是具有聚集诱导发光性能的基团,而识别基团对铀酰离子具有强的选择性识别能力。本发明的有机荧光分子相比于传统有机荧光探针而言,对铀酰离子的检测不存在浓度淬灭的问题,可以显著改善探针的检测范围,并且可以同时提高灵敏度和抗干扰能力,实现检测限、检测范围和选择性兼优兼顾。
Description
技术领域
本发明涉及基于聚集诱导发光的铀酰离子检测的有机荧光分子。
背景技术
随着核技术和核工业的发展,放射性废物的排放与危害越来越严重,铀作为一种重金属元素,它的化学毒性会造成肾小球细胞坏死和肾小管的萎缩、肝炎及神经系统等病变;作为放射性核素,铀的辐射损伤会使人发生基因突变并且致癌。因此,放射性铀废物的检测与安全有效处置是一个必须解决的问题。世界卫生组织建议饮用水中的铀酰离子浓度应该低于30μg/L,通过对水体中铀含量的测定,将为环境监测和人体健康风险评估提供重要依据。
在水体中铀通常以铀酰离子(UO2 2+)的形式存在,荧光检测法因其显著优点,是目前检测水体中铀酰离子最主要的测试方法。近十几年来,荧光分析法不断朝着高效、痕量、微观、快速和自动化的方向发展,方法的灵敏度、准确度和选择性日益提高,方法的应用大大扩展。而对于铀酰离子荧光检测法,通常是向体系中加入荧光探针来增强荧光,以实现对铀酰离子含量的测试。目前常用的荧光探针主要包括无机酸/盐类、生物探针(如DNA酶蛋白)和有机荧光探针类等。目前无机酸/盐类可以达到较低的检测限,但是选择性和检测范围不佳,还有待提高;DNA酶或蛋白等生物类探针虽然具有好的选择性和较低的检测限,但是方法较为复杂且活体选择和生物分离的成本都太高,不利于现场检测。有机荧光探针则因为存在浓度猝灭的问题(浓度猝灭是指有机荧光分子在稀溶液中呈现较高的发光效率,但随着荧光分子浓度的增加,由于分子间的相互作用导致体系荧光降低或猝灭,即发生了聚集导致发光猝灭(aggregation-caused quenching,ACQ)现象,简而言之,浓度增加导致聚集,从而发光猝灭),故有机荧光探针只能在稀溶液中使用,使检测范围随之降低。此外,有机荧光探针在对铀酰离子检测的实际应用中,工作环境基本都是水溶液,而大多数的有机荧光分子都是疏水性的,即使稀浓度有机荧光分子在水溶液中也不可避免地会发生聚集或沉淀导致ACQ效应,这在一定程度上也降低了体系的检测范围(简而言之,分子疏水性导致聚集,从而发光猝灭)。即,目前的有机荧光探针无法实现检测限、检测范围和选择性兼优兼顾。
发明内容
本发明是针对上述技术问题,提供的一种检测限、检测范围和选择性方面兼优兼顾的有机荧光分子。
为实现上述目的,本发明采用的技术方案如下:
基于聚集诱导发光的铀酰离子检测的有机荧光分子,所述有机荧光分子是利用具有聚集诱导发光性能的基团作为发光基团,和对铀酰离子具有强的选择性识别能力的识别基团,通过化学修饰合成的。
优选的,所述有机荧光分子为AIE型有机荧光分子;识别基团的结构式为
其中,所述发光基团为TPE,其结构式如下:
进一步的,所述发光基团在有机荧光分子中时,其被识别基团部分取代:
其中,在发光基团中R1、R2、R3、R4处为H,并且,该四个位置均为可被识别基团取代的取代位,该四个取代位结构上是处于相同位置的。
更进一步的,所述R1位和R4位分别被同一结构式的识别基团取代,且取代的识别基团各选自以下结构式中的任一种其实质上即是选取该三种识别基团的中任意一种,然后将该种识别基团的两个分别取代发光基团上处于对角线位置的取代位上。被取代后所获得的有机荧光分子分别为如下结构式:
作为另一种优选方案,R1、R2、R3、R4处分别被相同结构式的识别基团取代,且取代的识别基团各选自以下结构式中的任一种: 其实质上即是选取该三种识别基团的中任意一种,然后将该种识别基团的四个分别取代到发光基团上的取代位上。取代后得到的荧光分子结构式如下:
上述方案针对目前国际上对于铀酰离子检测的荧光增强剂或荧光探针极少能够做到兼顾检测限和选择性,且存在浓度淬灭、检测范围一般较窄的问题。本项目利用具有聚集诱导发光(AIE)性能的基团作为发光基团,和对铀酰离子具有强的选择性识别能力的识别基团,通过化学修饰合成一种检测限、检测范围和选择性方面兼优兼顾的有机荧光分子。
针对传统有机荧光分子的浓度增大,而发生荧光猝灭问题,选用具有聚集诱导发光性质的四苯基乙烯(TPE)作为发光基团,该基团在溶液态(自由状态)下,分子的激发态主要是通过分子内转动即非辐射跃迁的方式退激,宏观上表现为荧光淬灭,荧光强度减弱;相反,在聚集态或固态下,分子内的转动受到限制即非辐射跃迁的速率大大降低,因此辐射跃迁成为激子退激发的主要形式,宏观上表现为荧光增强。因此当分子浓度增大时荧光增强,有效解决了传统分子浓度猝灭问题,极大的拓展了对铀酰的检测范围。
由于是荧光分子与铀酰离子选择性结合,导致荧光光谱改变,根据光谱的变化量确定体系中铀酰离子的浓度,干扰金属是指该金属离子也能与荧光分子结合,从而导致荧光光谱改变,从而对结果造成影响。而通常水体中除了铀酰离子外,还有其他常见金属和重金属离子,这些金属即为干扰金属,会极大的干扰对铀酰离子的检测,对结果产生影响和误差。本发明选择的识别基团可以有效地识别铀酰离子与之配位,能够有效排除其他金属离子的干扰。
将TPE基团和识别基团,通过化学修饰合成本发明的新型AIE型有机荧光分子,当有机荧光分子的识别基团与铀酰离子选择性地进行配位反应,从而使整个荧光分子的立体结构和电子云发生变化,进而引起其荧光光谱的改变,根据光谱的变化量确定体系中铀酰离子的含量。本发明同时引入荧光量子效率高的发光基团和选择性识别能力强的识别基团,可以同时提高荧光探针的检测限和选择性,从而实现对铀酰离子的检测。
与现有技术相比,本发明具有以下有益效果:
(1)本发明的有机荧光分子相比于传统有机荧光探针而言,对铀酰离子的检测不存在浓度淬灭的问题,可以显著改善探针的检测范围。
(2)本发明的有机荧光分子引入荧光量子效率高的发光基团和选择性识别能力强的识别基团,可以同时提高灵敏度和抗干扰能力,实现检测限、检测范围和选择性兼优兼顾。
附图说明
图1为实施例中单位取代的有机荧光分子合成路线图。
图2为实施例中TPE-SA合成路线图。
图3是实施例材料TPE-SA的核磁共振氢谱图。
图4是实施例材料TPE-SA的核磁共振碳谱图。
图5是实施例材料TPE-SA滴定铀酰离子的荧光光谱图和实物图。
具体实施方式
下面结合附图说明和实施例对本发明作进一步说明,本发明的方式包括但不仅限于以下实施例。
本实施例的目的是为了提供一种检测限、检测范围和选择性方面兼优兼顾的有机荧光分子,由于本申请中有机荧光分子是利用具有聚集诱导发光性能的基团作为发光基团,和对铀酰离子具有强的选择性识别能力的识别基团,通过化学修饰合成的。本申请中的有机荧光分子是以四苯基乙烯作为分子骨架,通过偶联反应在不同位置修饰上不同数目的偕胺肟基团、salophen基团或噻唑苯酚基团。对于单取代的化合物可由为初始原料1-(4-苯硼酸频哪醇酯)-1,2,2-三苯乙烯,通过Suzuki偶联、缩合等多步反应生成,具体合成路线如图1所示。相应的,对于对位二取代和四取代的化合物(TPE-BAO、TPE-BSA、TPE-BTZ和TPE-TAO、TPE-TSA和TPE-TTZ),可通过相同的合成路线进行,只是起始原料更换为1,2-(4-苯硼酸频哪醇酯)-1,2-二苯乙烯,1,2,3,4-(4-苯硼酸频哪醇酯)-1,2-二苯乙烯。此外,还可4个取代位同时分别被一个相同种类的识别基团取代取代,即本申请中的有机荧光分子可在发光基团4个取代位上同时取代(即四个取代位均被同一结构式的四个识别基团取代)、对角线取代(即四个取代位中处于对角线位置的两个取代位均被同一结构式的两个识别基团取代)或单位取代(即任一取代位被识别基团取代),其最终得到的有机荧光分子性能差异较小,因此,本实施例以单取代的TPE-SA有机荧光分子进行详细介绍,以检测本申请的有机荧光分子性能。
TPE-SA是以1-(4-苯硼酸频哪醇酯)-1,2,2-三苯乙烯、4-溴苯胺、水杨醛为原料,通过Suzuki偶联反应和缩合反应得到,其合成路线图如图2所示。具体来说,步骤如下:将1-(4-苯硼酸频哪醇酯)-1,2,2-三苯乙烯1.1g(2.4mmol)、4-溴苯胺344mg(2mmol)、四(三苯基磷)钯230mg(0.2mmol)和碳酸钾829mg(6mmol)溶于甲苯20mL/乙醇8mL/水1mL混合溶剂中。在氮气保护下,溶液加热至75℃,回流反应24h,反应混合物变成黑色,停止加热并冷却至室温,用二氯甲烷萃取有机相,旋蒸后得到混合物。以二氯甲烷/石油醚(1:3)作洗脱剂,通过硅胶柱层析分离得到0.694g目标中间产物(淡黄色固体),收率68.2%。电离质谱(ESI-MS)m/z:C32H25N,计算值424.2060,实测值424.2063[M+H]+;1H NMR(600MHz,CHLOROFORM-D):δ7.39–7.34(m,2H),7.30–7.26(m,2H),7.13–7.04(m,13H),7.04–7.00(m,4H),6.73–6.68(m,2H),5.29(d,J=4.2Hz,2H);13C NMR(600MHz,CHLOROFORM-D):δ145.83,144.01,143.96,141.73,140.86,140.83,138.90,131.81,131.56,131.48,131.46,131.08,127.84,127.81,127.75,127.72,126.51,126.44,125.42,115.45。
接着将上述得到的产物(100mg,0.24mmol)和水杨醛35mg(0.28mmol)溶于5mL甲醇中。在氮气保护下,反应液在75℃下加热反应4h,反应混合物变成黄色。冷却至室温,过滤得到黄色固体,并于四氢呋喃/石油醚的混合溶剂中重结晶。最终得到0.11g目标化合物(深黄色固体),收率86.9%。ESI-MS m/z:C39H29NO,计算值528.2322,实测值528.2324[M+H];1HNMR(400MHz,DMSO-D6)δ12.89(s,1H),8.95(s,1H),7.68(d,J=8.5Hz,2H),7.63(d,J=6.7Hz,1H),7.49–7.35(m,5H),7.04(ddt,J=28.3,21.5,8.1Hz,19H);13C NMR(600MHz,TETRAHYDROFURAN-D):δ163.03,161.55,147.69,143.84,143.78,143.05,141.32,140.59,139.07,138.06,132.84,132.38,131.82,131.31,131.24,127.62,127.55,127.49,127.45,126.42,126.36,126.29,125.75,121.58,119.57,118.63,116.84(如图3和4)。由此可知,该最终产物的结构与理论上一致,即最终得到的即为TPE-SA有机荧光分子其中,所述发光基团是具有聚集诱导发光性能的基团,而识别基团对铀酰离子具有强的选择性识别能力。
将得到的材料TPE-SA对铀酰离子进行荧光滴定,可得到如图5所示的荧光光谱图和实物图。具体步骤如下:取一定重量的本发明有机荧光分子溶解于四氢呋喃(THF)中配置成原液,在相同体积的H2O/THF混合溶液中(H2O体积分数为85%),分别加入相同体积的原液和不同体积的铀标准溶液,反应足够时间后,经过测量荧光的变化与铀酰离子浓度的线性关系,得到如下表1所示数据,其检测限为2.3×10-9M,检测范围为3×10-9–9.2×10-6M,并且无其他金属离子干扰,抗干扰能力很强。可知,当有机荧光分子的识别基团与铀酰离子选择性地进行配位反应,从而使整个荧光分子的立体结构和电子云发生变化,进而引起其荧光光谱的改变,根据光谱的变化量确定体系中铀酰离子的含量。
同样的,以常见铀酰离子的荧光探针,2,6-pyridinedicarboxylic acid、sulfo-Salophen、Trimetazidine、PCSA分子进行对比检测(其检测方式及步骤均与现有技术中的相同,因此不做赘述),得到如下表1所示的检测结果:
表1
由上表可知,本发明的有机荧光分子相对于其他的荧光分子而言,其检测限达到了10-9M,相比2,6-pyridinedicarboxylic acid,sulfo-Salophen,Trimetazidine具有更低的检测限,与此同时,本发明的有机荧光分子检测范围为10-9–10-6M,相比其他分子而言,具有更宽的检测范围和更好的抗干扰能力。
上述实施例仅为本发明的优选实施方式之一,不应当用于限制本发明的保护范围,但凡在本发明的主体设计思想和精神上作出的毫无实质意义的改动或润色,其所解决的技术问题仍然与本发明一致的,均应当包含在本发明的保护范围之内。
Claims (6)
3.根据权利要求2所述的基于聚集诱导发光的铀酰离子检测的有机荧光分子,其特征在于,所述R1位被识别基团取代,而R2、R3、R4处仍为H。
4.根据权利要求2所述的基于聚集诱导发光的铀酰离子检测的有机荧光分子,其特征在于,所述R1位和R4位分别被同一结构式的识别基团取代,而R2、R3处仍为H。
5.根据权利要求2所述的基于聚集诱导发光的铀酰离子检测的有机荧光分子,其特征在于,R1、R2、R3、R4处分别被相同结构式的识别基团取代。
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