CN116478180A - 一种荧光大环及其在硝基芳香族化合物监测中的应用 - Google Patents
一种荧光大环及其在硝基芳香族化合物监测中的应用 Download PDFInfo
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Abstract
本发明公开了一种荧光大环及其在硝基芳香族化合物监测中的应用。本发明所设计的新型荧光大环分子具有良好的荧光量子产率，对多种硝基芳香族化合物展现出良好的荧光淬灭响应性，可用于硝基芳香族化合物监测。
Description
技术领域
本发明属于有机化学材料技术领域，具体涉及一种荧光大环及其在硝基芳香族化合物监测中的应用。
背景技术
硝基芳香族化合物(NACs)是一类苯环上含有一个或多个硝基的化合物，广泛应用于染料、炸药、农药等物品的生产；同时，它们广泛存在于工业废水、土壤和其他环境中。据报道，即使小剂量的NACs也会导致致突变性，接触这类化合物具有致畸性和致癌性的风险；因此，NACs对环境、动物和人类的危害很大。此外，由于这些污染物在水和土壤中的沉积会影响动物和人类的健康，NACs被认为是存在于水和土壤中的有毒污染物。因此，需要采取有效措施监测水体和土壤中NACs的含量。
近年来报道的吸附剂具有高表面积和高吸附能力，用于萃取和去除环境污染物的多孔材料也在不断发展。基于超分子大环化合物晶体的有机材料发展迅速，应用于生物医药以及分子识别等领域，其中一类大环化合物看似是无孔材料，但却拥有着可供客体分子利用的空腔结构或者晶格空洞，此类材料可以通过这类特殊的空腔结构与客体产生的主客体相互作用从而达到吸附某些特定的分子的作用。
发明内容
本发明的目的是提供一种新型荧光大环分子，作为发光材料应用于硝基芳香族化合物监测。
为了实现上述目的，本发明采用以下技术方案：
一种荧光大环分子，其结构式如下式所示：
上述荧光大环分子在制备硝基芳香族化合物检测产品中的应用。进一步地，所述硝基芳香族化合物选自对氟硝基苯、4-硝基-2-(三氟甲基)乙酰苯胺、5,5'-二巯基(2-硝基苯甲酸)、对硝基苯酚或三硝基苯酚。
本发明所设计的新型荧光大环分子P具有良好的荧光量子产率，对多种硝基芳香族化合物展现出良好的荧光淬灭响应性，可用于硝基芳香族化合物监测。
附图说明
图1为化合物P的核磁共振氢谱分析。
图2为化合物P的核磁共振质谱分析。
图3为化合物P对硝基苯类化合物荧光淬灭效果的拟合曲线图。
具体实施方式
下面结合附图和具体实施例对本发明作进一步详细说明，但不应理解为对本发明的限制。在不背离本发明精神和实质的情况下，对本发明方法、步骤或条件所作的修改或替换，均属于本发明的范围。实施例中未注明具体条件的实验方法及未说明配方的试剂均为按照本领域常规条件。
实施例1
荧光大环P的制备
P-1的合成：将2,5-二溴噻吩(0.48g,2mmol)，4-甲酰基苯基硼酸(0.72g,4.80mmol)，K2CO3(0.70g,5mmol)和N,N-二甲基甲酰胺(5mL)在N2氛围下混合30分钟，然后放入四(三苯基膦)钯(0.12g,0.1mmo1)，在100℃下搅拌反应12小时。反应完成，自然冷却后将所得橙色悬浮液过滤并用氯仿萃取。柱色谱分离，得到目标产物为褐色固体0.50g，产率84％。1H NMR(400MHz,CDCl3)：10.02(s,2H),7.93(d,4H),7.80(d,4H),7.50(s,2H)；13C NMR(101MHz,CDCl3):190.32,142.80,138.40,134.39,134.13,129.51,125.27,124.87.
P-2的合成：将化合物P-1(1g,3.40mmol)溶解到四氢呋喃和甲醇的混合溶剂(VTHF:VMeOH＝25:1；52mL)中，在冰浴条件下加入硼氢化钠(1g,6mmol)，室温下反应30min后加入去离子水淬灭反应，过滤后干燥得到黄色固体P-2(0.9g,0.3mmol)，产率90％。1H NMR(400MHz,DMSO)：7.65(d,4H),7.51(s,2H),7.37(d,4H),5.28(s,2H),4.52(s,4H).
P-3的合成：将化合物P-2(1g,3.3mmol)加入到250mL四氯化碳中形成悬浊液，冰浴滴加PCl3(3mL,33mmol)的四氯化碳(10mL)溶液，室温下反应24h，反应结束后盐水、饱和碳酸氢铵和盐水洗涤。最后，柱色谱分离得到化合物P-3(0.56g,1.7mmol)，产率50％。1H NMR(400MHz,DMSO)：7.72(d,4H),7.60(s,2H),7.50(d,4H),4.80(s,4H).
P-4的合成：将化合物P-3(1.1g,3.3mmol)溶解到20mL的二氯甲烷中，加入三氯化铝(0.9g,66mmol)后滴加对苯二甲醚(4.6g,33mmol)的二氯甲烷(30mL)溶液，室温下反应1h，加去离子水淬灭反应，最后柱色谱分离得到化合物P-4(880mg，1.6mmol)，产率50％。1HNMR(400MHz,CDCl3)：7.52(d,4H),7.22(d,6H),6.81(d,2H),6.75–6.68(m,4H),3.96(s,4H),3.78(s,6H),3.73(s,6H)；13C NMR(101MHz,CDCl3)：152.45,150.58,142.20,139.15,131.01,129.54,128.36,124.49,122.47,115.75,110.30,76.32,76.00,75.68,54.94,54.56,34.71.
P的合成：取化合物P-4(160mg,0.3mmol)，多聚甲醛(24mg)溶解到二氯甲烷(20mL)中，室温下滴加三氟化硼乙醚(20μL)，反应25min后加入饱和碳酸氢钠溶液(10mL)淬灭反应，柱色谱分离得到化合物P(80mg,0.07mmol)，产率50％。1H NMR(400MHz,CDCl3)：7.53(s,4H),7.45(s,4H),7.20(dd,12H),6.70(d,8H),3.99-3.84(m,12H),3.79-3.65(m,24H)。
化合物P的核磁共振氢谱图如图1所示，化合物P的核磁共振质谱图如图2所示。
取1mg化合物P溶于DMF溶液中，以硫酸奎宁作为参照进行荧光量子产率计算。
表1化合物P荧光量子产率计算结果
| ΦX | ΦST | KX | KST | ηX | ηST |
| 0.14 | 0.54 | 3893837 | 19762323 | 1.536 | 1.336 |
ST：Quinine Sulphate；Φ：荧光量子产率；K：不同浓度荧光化合物溶液紫外吸收与荧光释放积分面积拟合曲线斜率；η：不同溶剂的折光率；X：化合物P.
由表1的结果可知，大环化合物P其荧光量子产率为0.14，因此可作为发光材料进行应用。
实施例2
化合物P对硝基芳香族化合物的淬灭响应性效果测试
采用下式所示不同的硝基芳香族化合物(NACs)对化合物P的DMF溶液进行滴定，测定加入NACs前后的化合物P溶液的荧光强度F0和Fi。
之后通过斯顿-伏尔莫公式(Stern–Volmer)计算硝基芳香族化合物对化合物P的淬灭系数KSV：(F0/Fi)＝Ksv[Q]+1，F0和Fi分别为加入NACs前后的化合物P溶液的荧光强度，Ksv为猝灭系数(M-1)，Q(μM)为NACs在溶液中的浓度。
表2检测限LoD的计算
通过检测限的计算结果可知，化合物P对于对氟硝基苯的检测限可达0.11μM，远低于其他化合物。根据Nagarkar等人报道的TNP对其合成的MOF淬灭系数Ksv为3.5×104M-1，而TNP对大环P的淬灭系数可达3.8×104M-1。结合表2中的计算结果，可以看出大环P可以对对氟硝基苯、三硝基苯酚等硝基芳香族化合物展现出良好的淬灭响应性。
Claims (3)
1.一种荧光大环分子，其结构式如下式所示：
2.权利要求1所述的荧光大环分子在制备硝基芳香族化合物检测产品中的应用。
3.根据权利要求3所述的应用，其特征在于：所述硝基芳香族化合物选自对氟硝基苯、4-硝基-2-(三氟甲基)乙酰苯胺、5,5'-二巯基(2-硝基苯甲酸)、对硝基苯酚或三硝基苯酚。
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