CN106543126B - 基于香豆素对no2的荧光淬灭效应的荧光探针及其制备方法和应用 - Google Patents
基于香豆素对no2的荧光淬灭效应的荧光探针及其制备方法和应用 Download PDFInfo
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Abstract
本发明公开了一种基于香豆素对NO2的荧光淬灭效应的荧光探针及其制备方法和应用。利用3‑N,N‑二甲胺基苯酚、三氯氧磷和无水DMF制备4‑N,N‑二甲胺基‑2‑羟基‑苯甲醛,然后利用4‑N,N‑二甲胺基‑2‑羟基‑苯甲醛和三苯基膦烯基乙酸乙酯制备7‑N,N‑二甲胺基‑香豆素,再将其与三氯氧磷和无水DMF反应制得7‑N,N‑二甲胺基‑3‑醛基香豆素,最后利用7‑N,N‑二甲胺基‑3‑醛基香豆素和盐酸羟胺、三乙胺反应得到探针7‑N,N‑二甲胺基‑3‑肟基香豆素,该探针可用于对NO2进行检测,探针与NO2发生检测作用后,荧光强度淬灭98%。
Description
技术领域
本发明涉及二氧化氮检测技术领域,更具体地,本发明涉及一种基于香豆素对NO2的荧光淬灭效应的荧光探针及其制备方法和应用。
背景技术
NO2作为硝基脂肪族爆炸物的降解产物,是环境中的大气污染物,发展针对NO2的新型检测方法对于维护公共安全、预防环境污染等具有十分重要的意义。荧光淬灭法是通过以荧光淬灭型小分子为传感单元构造大分子或共聚物传感材料,可实现对检测对象基于“一点接触、多点响应”的超级淬灭,具有极高的灵敏度,在分析检测领域的发展趋势之一,其中荧光小分子是实现传感材料超级淬灭的核心和关键。香豆素分子具有制备简单、Stokes位移大、荧光亮度高等优点,在染料、传感及分析检测领域具有很好的应用前景,目前国内外以香豆素为荧光团,发展了各式各样的荧光探针用于金属离子、自由基以及无机小分子的标记与检测,然而目前仍未见基于香豆素的荧光探针用于NO2的荧光淬灭检测应用。
发明内容
目前针对二氧化氮气体的高选择性荧光检测大多基于荧光增强型,这类荧光小分子无法实现基于“一点接触、多点响应”的超级淬灭,进而对NO2的检测灵敏度还有待进一步提升,发展基于香豆素的淬灭型荧光小分子是实现NO2荧光超级淬灭的关键,有助于提高对NO2的检测灵敏度。
本发明为实现基于香豆素对NO2的荧光淬灭检测,提供了以香豆素为荧光团,肟基为NO2识别基团,通过分子设计调控探针识别机制,构筑得到新型淬灭型探针,以达到基于香豆素对NO2的荧光淬灭检测的新方法。本发明的一种实施方式采用以下技术方案:
一种基于香豆素对NO2的荧光淬灭效应的荧光探针,该探针的结构如下:
上述基于香豆素对NO2的荧光淬灭效应的荧光探针的制备方法包括如下步骤:
(1)制备4-N,N-二甲胺基-2-羟基-苯甲醛
将3-N,N-二甲胺基苯酚溶于干燥的DMF中,并在室温下逐滴滴加至由三氯氧磷和无水DMF新制的Vilsmeier Haack试剂中,接着室温搅拌至少15min,然后升温至30~40℃反应至少15min,再升温至80~90℃反应30~40min,冷却至室温,将反应混合物快速倒入大量冰水中,所得溶液用Na2CO3中和,收集沉淀并经过滤、水洗、干燥后得到4-N,N-二甲胺基-2-羟基-苯甲醛;
(2)制备7-N,N-二甲胺基-香豆素
将4-N,N-二甲胺基-2-羟基-苯甲醛和三苯基膦烯基乙酸乙酯在氩气保护下加热至180~185℃反应1~1.5h,冷却至室温,粗产物经硅胶柱色谱分离纯化得到7-N,N-二甲胺基-香豆素;
(3)制备7-N,N-二甲胺基-3-醛基香豆素
将7-N,N-二甲胺基-香豆素溶于干燥的DMF中,并在室温下逐滴滴加至由三氯氧磷和无水DMF新制的Vilsmeier Haack试剂中,然后升温至55℃反应 3.5~4h,冷却至室温并搅拌过夜,接着将反应混合液倒入大量冰水中,静置后过滤,收集沉淀物干燥,得到黄色产物即7-N,N-二甲胺基-3-醛基香豆素;
(4)制备7-N,N-二甲胺基-3-肟基香豆素
首先将7-N,N-二甲胺基-3-醛基香豆素溶于乙醇溶液中,接着将盐酸羟胺和三乙胺加入上述溶液中,加热至65~70℃反应3~3.5h,停止反应,旋转蒸发除去残余溶剂得到粗产物,于乙醇中重结晶得到黄色产物即探针7-N,N-二甲胺基-3-肟基香豆素。7-N,N-二甲胺基-3-肟基香豆素具有一定的水溶性,在反应停止后,不能用水洗涤,而是直接旋转蒸发除去有机残液。
上述基于香豆素对NO2的荧光淬灭效应的荧光探针用于对NO2进行检测。
将获得的新型探针7-N,N-二甲胺基-3-肟基香豆素溶于乙腈溶液中,通过紫外吸收光谱仪考察其紫外吸收光谱范围和中心吸收波长,通过荧光分光光度计考察其荧光发射光谱范围和中心发射波长。以荧蒽为参比物质,借助紫外吸收和荧光发射获得新型探针的荧光量子产率。
将新型探针溶于乙腈溶液中,通入一定浓度的NO2,考察新型探针对NO2的检测时间;加入不同的活性小分子,考察新型探针对NO2的选择性响应;通入适量浓度NO2反应一定时间后,考察新型探针对NO2的荧光淬灭效果。
与现有技术相比,本发明通过分子设计、化学合成获得新型探针7-N,N-二甲胺基-3-肟基香豆素。新型探针紫外吸收光谱范围为325~475nm,中心吸收波长为411nm,新型探针荧光发射光谱范围为425~600nm,中心发射波长为482nm。新型探针与NO2发生检测作用后,荧光量子产率由0.58减弱至0.022,荧光强度淬灭98%,新型探针的天蓝色荧光消失。
附图说明
图1为本发明新型探针的制备路线。
图2为本发明新型探针自身的紫外吸收光谱。
图3为本发明新型探针自身的荧光发射光谱。
图4为本发明新型探针对NO2的荧光响应行为图谱。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白,以下结合附图及实施例,对本发明进行进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。
7-N,N-二甲胺基-3-肟基香豆素的制备路线如图1所示。其中化合物1是7-N,N- 二甲胺基-3-肟基香豆素,化合物2是7-N,N-二甲胺基-3-醛基香豆素,化合物3是 7-N,N-二甲胺基-香豆素,化合物4是4-N,N-二甲胺基-2-羟基-苯甲醛,化合物5是 3-N,N-二甲胺基苯酚。
实施例1 4-N,N-二甲胺基-2-羟基-苯甲醛的制备
3-N,N-二甲胺基苯酚(10.5g,0.075mol)溶于20mL干燥的DMF中,并在室温下逐滴滴加至由三氯氧磷(8.2mL,0.09mol)和无水DMF(17mL,0.22mol) 新制的Vilsmeier Haack试剂中,接着室温搅拌20min,升温至40℃反应20min,再升温至80℃反应30min。冷却至室温,反应混合物快速倒入大量冰水中,上述溶液用NaHCO3中和,收集沉淀并经过滤、水洗、干燥后得到目标产物8.8g,产率65%。
实施例2 7-N,N-二甲胺基-香豆素的制备
4-N,N-二甲胺基-2-羟基-苯甲醛(5g,30mmol)和三苯基膦烯基乙酸乙酯 (12g,35mmol)在氩气保护下加热至180℃反应1h,冷却至室温,粗产物经硅胶柱色谱分离纯化得到目标产物5.5g,产率62%。
实施例3 7-N,N-二甲胺基-3-醛基香豆素的制备
7-N,N-二甲胺基-香豆素(0.75g,4.0mmol)溶于干燥的30mL的DMF中,并在室温下逐滴滴加至由三氯氧磷(1.8mL,20mmol)和无水DMF(4.0mL, 50mmol)新制的VilsmeierHaack试剂中,接着升温至55℃反应4h,冷却至室温并搅拌12h,接着将反应混合液倒入大量冰水中,静置后过滤,收集沉淀物干燥,得到目标产物0.30g,产率30%。
实施例4 7-N,N-二甲胺基-3-肟基香豆素的制备
首先7-N,N-二甲胺基-3-醛基香豆素(0.10g,0.46mol)溶于15mL乙醇溶液中,接着将盐酸羟胺(0.097g,1.39mmol)和三乙胺(0.19mL,1.39mmol) 加入上述溶液中,加热至65℃反应3h,停止反应,旋转蒸发除去残余溶剂得到粗产物,经乙醇重结晶,得到黄色目标产物80mg,产率80%。
实施例5新型探针自身光谱性质
将新型探针7-N,N-二甲胺基-3-肟基香豆素(11.6mg)溶于DMSO溶液(5.0 mL)配制成1.0×10-2mol/L探针储备液,接着将探针储备液用乙腈稀释至1.0× 10-6mol/L探针测试液。将上述探针测试液置于紫外吸收光谱仪上在800~200nm 范围内扫描紫外吸收光谱,探针自身的紫外吸收光谱如图2所示,紫外吸收光谱范围为325~475nm,中心吸收波长为411nm。将上述探针测试液置于比色池中放于荧光分光光度计中以411nm为固定激发波长扫描荧光发射光谱,探针自身的荧光发射光谱如图3所示,荧光发射光谱范围为425~600nm,中心发射波长为482nm。
实施例6新型探针对NO2的荧光检测行为
从二氧化氮标准气瓶(50ppm,4L)引出经配气系统稀释成一定浓度的NO2气体(20ppm)通入上述新型探针标准液中(1.0×10-6mol/L),分别反应1、3、 6、10、15min,接着在荧光分光光度计上考察其荧光强度,发现探针在10min 后对NO2的荧光淬灭达到最大;新型探针标准液中(1.0×10-6mol/L)加入不同的潜在干扰物(H2S、SO2、NO、H2O2、NO2 -和NO3 -),上述干扰物的浓度为NO2的100倍,反应10min,发现除了NO2外干扰物并没有引起探针荧光淬灭,表明新型探针对NO2具有高选择性荧光淬灭响应。将上述探针标准液与10ppm的NO2反应10min,于荧光分光光度计上在411nm激发下测试482nm的荧光强度,初始荧光强度淬灭了98%,荧光量子产率由0.58降低至0.022,表明新型探针对NO2展现出天蓝色的荧光淬灭响应。新型探针对NO2的荧光响应行为图谱见图4。
尽管这里参照本发明的解释性实施例对本发明进行了描述,但是,应该理解,本领域技术人员可以设计出很多其他的修改和实施方式,这些修改和实施方式将落在本申请公开的原则范围和精神之内。
Claims (3)
1.一种基于香豆素对NO2的荧光淬灭效应的荧光探针,其特征在于该探针的结构如下:
2.权利要求1所述的基于香豆素对NO2的荧光淬灭效应的荧光探针的制备方法,其特征在于包括如下步骤:
(1)制备4-N,N-二甲胺基-2-羟基-苯甲醛
将3-N,N-二甲胺基苯酚溶于干燥的DMF中,并在室温下逐滴滴加至由三氯氧磷和无水DMF新制的Vilsmeier Haack试剂中,接着室温搅拌至少15min,然后升温至30~40℃反应至少15min,再升温至80~90℃反应30~40min,冷却至室温,将反应混合物快速倒入大量冰水中,所得溶液用Na2CO3中和,收集沉淀并经过滤、水洗、干燥后得到4-N,N-二甲胺基-2-羟基-苯甲醛;
(2)制备7-N,N-二甲胺基-香豆素
将4-N,N-二甲胺基-2-羟基-苯甲醛和三苯基膦烯基乙酸乙酯在氩气保护下加热至180~185℃反应1~1.5h,冷却至室温,粗产物经硅胶柱色谱分离纯化得到7-N,N-二甲胺基-香豆素;
(3)制备7-N,N-二甲胺基-3-醛基香豆素
将7-N,N-二甲胺基-香豆素溶于干燥的DMF中,并在室温下逐滴滴加至由三氯氧磷和无水DMF新制的Vilsmeier Haack试剂中,然后升温至50~55℃反应3.5~4h,冷却至室温并搅拌过夜,接着将反应混合液倒入大量冰水中,静置后过滤,收集沉淀物干燥,得到黄色产物即7-N,N-二甲胺基-3-醛基香豆素;
(4)制备7-N,N-二甲胺基-3-肟基香豆素
首先将7-N,N-二甲胺基-3-醛基香豆素溶于乙醇溶液中,接着将盐酸羟胺和三乙胺加入上述溶液中,加热至65~70℃反应3~3.5h,停止反应,旋转蒸发除去残余溶剂得到粗产物,于乙醇中重结晶得到黄色产物即探针7-N,N-二甲胺基-3-肟基香豆素。
3.权利要求1所述的基于香豆素对NO2的荧光淬灭效应的荧光探针的应用,其特征在于该探针用于对NO2进行检测。
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