CN108727362A - 一类固体荧光小分子的合成与应用 - Google Patents
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Abstract
本发明涉及部分固体荧光小分子的简便合成方法、固体荧光现象和应用报道，并对其结构进行衍生。属于化学分析检测技术领域。其分子结构如下：该类小分子化合物易于合成，纯化步骤简单。本发明所述小分子化合物表现出(或潜在表现出)强的固体荧光，AIE性质良好。基于化合物ECB‑S设计的检测过氧化氢(H2O2)的探针能够实现体内外灵敏检测过氧化氢，具有重要的应用价值。
Description
本发明属于化学分析检测技术领域，具体涉及一类小分子的固体荧光报道及其在检测过氧化氢(H2O2)方面的应用。
背景技术
大部分传统有机染料在稀溶液里面发射很强的荧光，但是展现弱的或没有荧光在聚集状态，因为发生聚集诱导淬灭作用(ACQ)。但是目前报道的许多化合物在稀的溶液态有弱的或者没有荧光，相反在聚集态有很强的荧光，这种特别的现象叫做聚集诱导发光(AIE)。AIE现象主要通过在聚集态抑制分子内的旋转和振动，减少分子内发生非辐射跃迁导致发生很强的荧光。AIE现象由于其许多优点，也得到了广泛的应用，例如化学传感、OLED设备及生物传感。
发明内容
本发明目的之一在于提供一种简便高效的固体荧光小分子的合成方法；本发明之另一目的在于通过合成报道部分小分子化合物的固体荧光现象，推测其衍生物也应当有潜在的固体荧光现象，并对其运用于检测过氧化氢(H2O2)进行了有效性实验。
本发明解决问题采取的技术方案为，部分固体荧光小分子的合成及其衍生物，其分子结构式通式如下：。
合成路线如下：
具体合成方法如下：A、将化合物1(100.0mg,0.52mmol)分别与1倍单量的氰基苯并噻唑、氰基苯并恶唑、氰基苯并咪唑溶于2.0mL无水乙醇，加入40μL哌啶作催化剂，室温搅拌反应，析出固体，抽滤并用少量乙醇洗涤得到目标产物。B、将化合物2(100.0mg,0.52mmol)分别与1倍单量的氰基苯并噻唑、氰基苯并恶唑、氰基苯并咪唑溶于2.0mL无水乙醇，加入40μL哌啶作催化剂，室温搅拌反应，析出固体，抽滤并用少量乙醇洗涤得到目标产物。C、将化合物3(100.0mg,0.52mmol)分别与1倍单量的氰基苯并噻唑、氰基苯并恶唑、氰基苯并咪唑溶于2.0mL无水乙醇，加入40μL哌啶作催化剂，室温搅拌反应，析出固体，抽滤并用少量乙醇洗涤得到目标产物。
本发明通过采取一种简便快捷的合成方法合成部分小分子化合物，在温和的反应条件下，通过室温反应，反应过程中析出固体，产物通过乙醇洗涤纯化即可得到纯的产物，从而推广到其衍生物的合成。
本发明合成的一系列小分子展现出固体荧光，推测其衍生物也应当有潜在固体荧光现象，通过分子结构的变化，得到不同波长的固体荧光物质。
本发明通过365nm手提灯照射前后对比自然光照和365nm紫外灯照下化合物ECOMA-S、ECME-S、ECB-S表现出明显的固体荧光。
本发明通过具体测试化合物ECOMA-S、ECME-S、ECB-S在不同比例水和有机溶剂混合体系中的荧光发射变化，来验证该类化合物的固体荧光性质。
本发明通过具体测试化合物ECOMA-S、ECME-S、ECB-S在不同比例水和有机溶剂混合体系中的荧光发射波长随水的比例增加的变化，来进一步验证该类化合物的固体荧光性质。
本发明通过ECB-S分子设计出一种检测过氧化氢的荧光探针，以探究其的应用价值。过氧化氢能够氧化探针分子中溴代硼酸酯部分，水解释放出染料ECOMA-S，而发射波长蓝移而发射绿光(520nm)，从而实现特异性检测过氧化氢(H2O2)的目的。探针分子的响应过程如下：
本发明的荧光探针在加入50倍当量的过氧化氢(H2O2)作用后，在520nm处荧光发生很大的增强。
本发明所述的化合物表现出良好的固体荧光现象，以ECB-S设计探针分子对过氧化氢(H2O2)具有良好的响应，展现出好的灵敏度，有利于进一步拓展该类化合物在生物与化学等领域具有实际的应用价值，并将其固体荧光现象推广到一系列衍生结构。
附图说明
图1为本发明的化合物ECOMA-S、ECME-S、ECB-S在自然光照条件和365nm手提紫外灯照下的情况，a1-c1为自然光照下的情况，a2-c2为手提紫外灯照下固体荧光情况。
图2为本发明的化合物ECOMA-S、ECME-S、ECB-S的固体荧光发射归一化图，纵坐标为荧光强度，横坐标为波长。
图3为本发明的化合物ECOMA-S在DMF和水的混合溶剂中的AIE曲线，纵坐标为荧光强度，横坐标为含水量。
图4为本发明的化合物ECOMA-S在DMF和水的混合溶剂中发射波长随含水量变化，纵坐标为发射波长变化值，横坐标为含水量。
图5为本发明的化合物ECME-S在DMF和水的混合溶剂中的AIE曲线，纵坐标为荧光强度，横坐标为含水量。
图6为本发明的化合物ECME-S在DMF和水的混合溶剂中发射波长随含水量变化，纵坐标为发射波长变化值，横坐标为含水量。
图7为本发明的化合物ECB-S在DMF和水的混合溶剂中的AIE曲线，纵坐标为荧光强度，横坐标为含水量。
图8为本发明的化合物ECB-S在DMF和水的混合溶剂中发射波长随含水量变化，纵坐标为发射波长变化值，横坐标为含水量
图9为本发明的化合物ECB-S在PBS和30％乙腈中检测过氧化氢(H2O2)前后的紫外吸收变化归一化图，纵坐标为发射波长，横坐标为含水量。
图10为本发明的化合物ECB-S在PBS和30％乙腈中检测过氧化氢(H2O2)中的滴定实验，随着过氧化氢(H2O2)浓度增加，在430nm的波长激发下，520nm的荧光强度随过氧化氢(H2O2)浓度的增加而不断增强，加到50倍单量时达到最大值，实现了体外灵敏检测过氧化氢(H2O2)，纵坐标为荧光强度，横坐标为波长。
图11为本发明的化合物ECB-S在PBS和30％乙腈中检测过氧化氢(H2O2)浓度滴定实验散点图，随着过氧化氢(H2O2)浓度增加，在430nm的波长激发下，520nm的荧光强度随过氧化氢(H2O2)浓度的增加而不断增强，加到250微升(50倍单量)时达到最大值，实现了体外灵敏检测过氧化氢(H2O2)，纵坐标为荧光强度，横坐标为过氧化氢(H2O2)浓度。
图12本发明的化合物ECB-S在细胞内检测过氧化氢(H2O2)中的成像图，左边为加入50倍单量过氧化氢(H2O2)后，在430nm的波长激发下，在绿光通道呈现明显的绿光，右边为明场条件下的细胞形态图。
具体实施实例
实施例1：化合物ECOMA-S的合成
将化合物1(100.0mg,0.52mmol)与氰基苯并噻唑(90.0mg,0.52mmol)溶于2.0mL无水乙醇，加入40μL哌啶作催化剂，室温搅拌反应，析出橙黄色固体，抽滤并用少量乙醇洗涤得到目标产，橙黄色固体170.0mg，产率93.9％。1H NMR(400MHz,CDCl3)δ8.25(s,1H),8.01(d,J＝8.1Hz,1H),7.89(d,J＝7.9Hz,1H),7.46(t,J＝7.6Hz,1H),7.33(dd,J＝15.7,8.1Hz,1H),7.26(s,1H),6.47(dd,J＝8.7,2.0Hz,1H),6.38(s,1H),3.40(q,J＝7.1Hz,4H),1.33–1.12(m,6H).13C NMR(101MHz,CDCl3)δ156.0,153.0,152.8,151.3,136.9,130.1,125.9,124.5,122.4,96.9,45.1,12.5.
实施例2：化合物ECME-S的合成
将化合物2(100.0mg,0.48mmol)与氰基苯并噻唑(84.0mg,0.48mmol)溶于2.0mL无水乙醇，加入40μL哌啶作催化剂，室温搅拌反应，析出橙色固体，抽滤并用少量乙醇洗涤得到目标产，橙色固体164.0mg，产率94.2％。1H NMR(400MHz,CDCl3)δ8.55(s,1H),8.42(d,J＝9.1Hz,1H),8.01(d,J＝8.1Hz,1H),7.83(d,J＝7.9Hz,1H),7.45(t,J＝7.7Hz,1H),7.33(t,J＝8.0Hz,1H),6.37(d,J＝10.7Hz,1H),6.09(s,1H),3.91(s,3H),3.44(q,J＝7.1Hz,4H),1.24(t,J＝7.1Hz,6H).13C NMR(101MHz,CDCl3)δ161.1,140.7,134.2,126.2,124.8,122.5,105.1,92.8,55.5,45.0,12.7.
实施例3：化合物ECB-S的合成
将化合物3(100.0mg,0.25mmol)与氰基苯并噻唑(43.0mg,0.25mmol)溶于2.0mL无水乙醇，加入40μL哌啶作催化剂，室温搅拌反应，析出橙色固体，抽滤并用少量乙醇洗涤得到目标产，橙色固体130.0mg，产率92.2％。1H NMR(400MHz,CDCl3)δ8.62(s,1H),8.45(d,J＝9.1Hz,1H),8.03(d,J＝8.1Hz,1H),7.85(t,J＝6.9Hz,3H),7.49(d,J＝7.9Hz,2H),7.45(d,J＝7.3Hz,1H),7.34(t,J＝7.5Hz,1H),6.38(d,J＝8.6Hz,1H),6.12(s,1H),5.23(s,2H),3.37(q,J＝7.0Hz,4H),1.36(s,12H),1.15(t,J＝7.1Hz,6H).13C NMR(101MHz,CDCl3)δ160.4,153.9,135.2,134.3,130.5,126.3,126.0,124.9,122.9,121.3,83.9,70.5,45.3,24.8,12.4.
实施例4：化合物ECOMA-S、ECME-S、ECB-S的固体荧光性能测试
通过测试化合物ECOMA-S、ECME-S、ECB-S的固体荧光发射图谱及可视化条件下测试自然光照和365nm紫外灯照条件下的固体荧光。并通过AIE曲线来进一步证实该类化合物具有良好的固体荧光现象。
实施例5：基于化合物ECB-S荧光探针的应用
将探针分子溶于PBS(10mM，pH＝7.4)/CH3CN30％中配制成10.0×10-6mol/L的溶液，向其中加入不同浓度的过氧化氢(H2O2)，随着响应物浓度增加，探针在520nm处的荧光不断增强，说明探针能很好的检测外源性过氧化氢(H2O2)。通过细胞成像试验表明探针能用于内源性、外源性过氧化氢(H2O2)的检测，表现出了良好的生物适应能力，从而实现细胞内过氧化氢(H2O2)的检测。
Claims (2)
1.一种简便合成固体荧光小分子的方法。
2.一类固体荧光小分子的固体荧光现象及其结构衍生，其结构通式：
。
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