CN109970774A - 一种高灵敏度、可裸眼检测有机伯胺的荧光化合物ppab及其应用 - Google Patents
一种高灵敏度、可裸眼检测有机伯胺的荧光化合物ppab及其应用 Download PDFInfo
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Abstract
本发明公开了一种高灵敏度、可裸眼检测有机伯胺的荧光化合物PPAB及其应用。本发明中所述PPAB是通过吡咯并吡咯二酮与含氮芳香伯胺发生缩合反应及原位与BF3.Et2O发生配位作用得到。硼原子可与有机胺中的氮原子反应，且亚胺键在有机胺存在下易发生反应，所以本发明中将多个亚胺键和多个硼原子同时引入化合物中，即引入了多反应位点，将荧光化合物PPAB用于检测脂肪族伯胺，且检测过程中具有操作简便、反应迅速、选择性好、荧光信号抗光漂白性质优异、比色和荧光双模式检测的特点，可用于环境监测、食品安全检测等。
Description
技术领域
本发明属于分析检测技术领域，特别涉及一种高灵敏度、可裸眼检测有机伯胺的荧光化合物PPAB及其应用。
背景技术
作为一种重要的化工原料和中间体，有机胺类在工业、农业、医药等领域均具有十分广泛的应用，可作为医药中间体、促进剂、金属防腐剂、乳化剂等。其中，大部分胺都具有强烈的刺激性和腐蚀性，能刺激眼、气管、肺、皮肤和排泄系统，高浓度吸入可致死，因此有机胺的检测在化学物质泄露、食品安全以及环境检测等领域具有重要的意义。目前有机胺的检测方法有电化学法、色谱分析法和比色法等，但存在检测速度慢、灵敏度较低、设备复杂、成本较高等不足。因此，研发一类具有选择性好、效果明显、低成本、响应速度快、高灵敏的新型荧光探针成为迫切要求。
荧光分析具有方便、直观、实时、快速的特点，可检测有机胺的反应型荧光探针备受关注[(1)L.Zhai,M.Liu,P.Xue,J.Sun,P.Gong,Z.Zhang,J.Sun and R.Lu,J.Mater.Chem.C,2016,4,7939–7947.(2)Z.Jiao,Y.Zhang,W.Xu,X.Zhang,H.Jiang,P.Wu,Y.Fu,Q.He,H.Cao,and J.Cheng,ACS Sens.,2017,2,687–694.(3)D.Shi,X.Wang,S.Yu,F.Zhao,Y.Wang,J.Tian,L.Hu,X.Yu,and L.Pu,Eur.J.Org.Chem.,2018,8,1053–1059.(4)Y.Xu,D.Shi,X.Wang,S.Yu,X.Yu,and L.Pu,Eur.J.Org.Chem.,2017,33,4990–4994.(5)S.Mallick,F.Chandra and A.L.Koner,Analyst,2016,141,827–831]。然而，现有的荧光探针只能检测单一种类、检测速度慢、检测限较低，远远不能满足实际需求，此外，现有的荧光探针只能通过单模式(如比色或荧光)光响应实现检测；探针的发光波长均较短，为蓝色或者绿色[(1)Y.J.Diaz,Z.A.Page,A.S.Knight,N.J.Treat,J.R.Hemmer,C.J.Hawker,andJ.R.Alaniz,Chem.Eur.J.,2017,23,3562–3566.(2)A.R.Longstreet,M.Jo,R.R.Chandler,K.Hanson,N.Zhan,J.J.Hrudka,H.Mattoussi,M.Shatruk,and D.T.McQuade,J.Am.Chem.Soc.,2014,136,15493–15496]，使其应用受到了很大的限制。目前还没有文献实现对有机伯胺的高灵敏检测。
目前有机胺的荧光探针都是含单一反应位点的化合物，所以灵敏度较低。
发明内容
本发明的目的是针对有机胺荧光探针种类稀少、响应速度慢的不足，提供一种高灵敏度、可裸眼检测有机伯胺的荧光化合物PPAB及其应用。其中，PPAB是吡咯并吡咯氮杂BODIPY化合物的缩写。
本发明的目的通过如下技术方案实现。
一种高灵敏度、可裸眼检测有机伯胺的荧光化合物PPAB，其结构式为：
其中：R1为烷基、烷氧基或芳香取代基，且碳原子总数为6-24；R2为叔丁基、C6-C18的饱和直链烷基、C6-C18的饱和支链烷基或C6-C18的芳香取代基。
R1＝-(CH2)nCH3,n＝5～23,
进一步地，-O(CH2)nCH3,n＝5～23,
进一步地，
本发明还提供了一种高灵敏度、可裸眼检测有机伯胺的荧光化合物PPAB的应用，在溶剂中将所述荧光化合物PPAB与有机伯胺混合进行反应，然后进行紫外或荧光光谱检测。
进一步地，所述溶剂为1，4-二氧六环，所述有机胺为脂肪族伯胺。
进一步地，所述有机伯胺为挥发性脂肪族伯胺或非挥发性脂肪族伯胺，如1，3-丙二胺或1，4-丁二胺。
进一步地，所述荧光化合物PPAB的浓度为10-7～10-2mol/L。
进一步地，所述荧光化合物PPAB的浓度为10μmol/L。
进一步地，所述反应的时间为2～20分钟。
进一步的，有机伯胺的检测上限为100μmol/L。
在本发明中，所述荧光化合物化合物PPAB是通过吡咯并吡咯二酮与含氮芳香伯胺发生缩合反应及原位与BF3.Et2O发生配位作用得到。对于反应型荧光探针来说，引入多反应位点是提高荧光探针与有机胺反应速率的有效手段；含硼化合物中含有缺电子的硼原子，易被有机胺中富电子的氮原子进攻，发生解配位作用；在有机胺存在下，亚胺键(C＝N)易发生胺的易位反应和水解反应，所以本发明中将多个亚胺键和多个硼原子同时引入化合物中，即引入了多反应位点，进而提高荧光探针与有机胺反应速率，提高灵敏度。
相对于现有技术，本发明具有如下优点：
(1)本发明中引入了多反应位点，提高了荧光探针与有机胺反应速率，进而有效提高了检测有机胺的灵敏度，克服了目前有机胺的荧光探针都是含单一反应位点而灵敏度低的缺点；本发明提供的荧光化合物在脂肪族伯胺检测中具有操作简便、反应迅速、选择性好、荧光信号抗光漂白性质优异、比色和荧光双模式检测的特点；
(2)本发明提供的荧光化合物在脂肪族伯胺检测中具有比色和荧光双模式检测的特点；
(3)该方法在有机胺的检测研究领域具有实际的应用价值，可用于食品安全检测、环境监测等。
附图说明
图1为实施例1制备的荧光化合物PPAB1的高分辨质谱图；
图2为实施例2中的荧光化合物PPAB1在1，4-二氧六环中与1，3-丙二胺反应后溶液的时间依赖紫外可见光谱图；
图3为实施例3中的荧光化合物PPAB1在1，4-二氧六环中与1，3-丙二胺反应后溶液的时间依赖荧光发射光谱图；
图4实施例4制备的荧光化合物PPAB2的高分辨质谱图；
图5为实施例5中荧光化合物PPAB2在1，4-二氧六环中与1，4-丁二胺反应后溶液的时间依赖紫外可见光谱图；
图6为实施例6中荧光化合物PPAB2在1，4-二氧六环中与1，4-丁二胺反应后溶液的时间依赖荧光发射光谱图。
具体实施方式
下面结合实施例对本发明作进一步说明。经过研究和试验，发明人开发许多成功的实例，下面列举部分具体实施例，但本发明要求保护的范围并不局限于实施例表述的范围。
实施例1
制备荧光化合物PPAB1的反应方程式为：
(1)化合物1按照文献G.M.Fischer,M.Isomaeki-Krondahl,I.Goettker-Schnetmann,E.Daltrozzo and A.Zumbusch,Chemistry-A European Journal,2009,15,4857–4864所公开的方法制备。
(2)将化合物1(365mg，0.67mmol)和化合物2(1110mg，5.36mmol)溶于40mL甲苯，将反应体系加热至50℃，搅拌10分钟后，加入三乙胺(2.24g,22.11mmol)和TiCl4(1.52g,8.04mmol)，TLC检测原料反应完后，向反应液中加入BF3-Et2O(2.63g,18.56mmol)，继续搅拌30分钟，将反应液倒入200mL水中，用CH2Cl2萃取3次，无水NaSO4干燥，过滤，旋蒸除去溶剂，硅胶柱层析分离，得到PPAB1粗产物，用CH2Cl2/甲醇重结晶得到紫褐色固体，产率为20％。其高分辨质谱如图1所示。
实施例2～3为荧光化合物PPAB1用于有机伯胺的比色荧光检测。
实施例2
将PPAB1溶于1，4-二氧六环，得探针母液(10-3mol/L)，随后加入1，4-二氧六环稀释得到10-5mol/L的PPAB1溶液，加入1，3-丙二胺溶液(4×10-5mol/L)，测试不同反应时间其紫外谱图的变化，从图2可以看出，680nm和630nm处的吸收峰强度迅速降低，450nm处的吸收峰红移到480nm，3分钟时候已达到平衡，且溶液颜色由绿色变为黄色。
实施例3
将PPAB1溶于1，4-二氧六环，得探针母液(10-3mol/L)，随后加入1，4-二氧六环稀释得到10-5mol/L的PPAB1溶液，加入1，3-丙二胺溶液(4×10-5mol/L)，测试不同反应时间其荧光谱图的变化，从图3可以看出，695nm处的荧光强度下降，518nm处的荧光红移到544nm并随着荧光强度的增加，3分钟时候已达到平衡。
实施例4
制备荧光化合物PPAB2的反应方程式为：
(1)化合物1按照文献G.M.Fischer,M.Isomaeki-Krondahl,I.Goettker-Schnetmann,E.Daltrozzo and A.Zumbusch,Chemistry-A European Journal,2009,15,4857–4864所公开的方法制备。
(2)将化合物1(200mg,0.45mmol)和化合物3(725mg,1.79mmol)溶于40mL甲苯，将反应体系加热至50℃，搅拌10分钟后，加入三乙胺(1.50g,14.78mmol)和TiCl4(1.02g,5.38mmol)，TLC检测原料反应完后，向反应液中加入BF3-Et2O(1.78g,12.54mmol)，继续搅拌30分钟，将反应液倒入200mL水中，用CH2Cl2萃取3次，无水NaSO4干燥，过滤，旋蒸除去溶剂，硅胶柱层析分离，得到PPAB2粗产物，用CH2Cl2/甲醇重结晶得到紫褐色固体，产率为18％。其高分辨质谱如图4所示。
实施例5～6为荧光化合物PPAB2用于有机伯胺的比色荧光检测。
实施例5
将PPAB2溶于1，4-二氧六环，得探针母液(10-3mol/L)，随后加入1，4-二氧六环稀释得到10-5mol/L的PPAB2溶液，加入1，4-丁二胺溶液(4×10-5mol/L)，测试不同反应时间其紫外谱图的变化，从图5可以看出，684nm和632nm处的吸收峰强度迅速降低，453nm处的吸收峰红移到484nm，3分钟时候已达到平衡，且溶液颜色由绿色变为黄色。
实施例6
将PPAB2溶于1，4-二氧六环，得探针母液(10-3mol/L)，随后加入1，4-二氧六环稀释得到10-5mol/L的PPAB2溶液，加入1，4-丁二胺溶液(4×10-5mol/L)，测试不同反应时间其紫外谱图的变化，从图6可以看出，698nm处的荧光强度下降，520nm处的荧光红移到546nm并随着荧光强度的增加，3分钟时候已达到平衡。
上述实施例为本发明较佳的实施方式，但本发明的实施方式并不受上述实施例的限制，其它的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化，均应为等效的置换方式，都包含在本发明的保护范围之内。
Claims (10)
1.一种高灵敏度、可裸眼检测有机伯胺的荧光化合物PPAB，其特征在于，其结构式为：
其中：R1为烷基、烷氧基或芳香取代基，且碳原子总数为6-24；R2为叔丁基、C6-C18的饱和直链烷基、C6-C18的饱和支链烷基或C6-C18的芳香取代基。
2.根据权利要求1所述的荧光化合物PPAB，其特征在于：
R1＝-(CH2)nCH3,n＝5～23,
-O(CH2)nCH3,n＝5～23,
3.权利要求1所述的一种高灵敏度、可裸眼检测有机伯胺的荧光化合物PPAB，其特征在于：
R2＝-(CH2)nCH3，n＝5-17，
4.权利要求1-3任一项所述的高灵敏度、可裸眼检测有机伯胺的荧光化合物PPAB的应用，其特征在于：在溶剂中将荧光化合物PPAB与有机伯胺混合进行反应，然后进行紫外或荧光光谱检测。
5.根据权利要求4所述的应用，其特征在于：所述溶剂为1，4-二氧六环，所述有机伯胺为脂肪族伯胺。
6.根据权利要求4所述的应用，其特征在于：所述有机伯胺为1，3-丙二胺或1，4-丁二胺。
7.根据权利要求4所述的应用，其特征在于：所述荧光化合物PPAB的浓度为10-7～10- 2mol/L。
8.根据权利要求7所述的应用，其特征在于：所述荧光化合物PPAB的浓度为10μmol/L。
9.根据权利要求4所述的应用，其特征在于：反应时间为2～10分钟。
10.根据权利要求4所述的应用，其特征在于：所述有机伯胺的检测上限为100μmol/L。
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