CN110698390A - 一种识别亚硫酸氢根的荧光探针及其制备方法和检测方法 - Google Patents
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Abstract
本发明公开了一种识别亚硫酸氢根的荧光探针及其制备方法和检测方法。其制备是(1)将4‑乙烯基吡啶、1,4‑二溴‑2,3,5,6‑四甲基苯和醋酸钯加入三乙胺中混合,反应,得A品;(2)将A品用二氯甲烷完全溶解成黑色悬液,得B品;(3)将B品洗涤,得C品;(4)将C品静置分层,将最下层的二氯甲烷层分离出来后,干燥,旋干,重结晶,得D品;(5)将D品加入N,N‑二甲基甲酰胺中溶解,然后加入1‑溴癸烷,加热反应,反应液中加入乙醚至其完全沉淀,抽滤,用乙醚洗涤两次,烘干,得到探针。是在水溶液中检测亚硫酸氢根。本发明的荧光探针能够对亚硫酸氢根进行识别,且识别成本低,操作简单,结果可视,灵敏度高,选择性好。
Description
技术领域
本发明涉及一种荧光探针及其制备方法和应用,特别是一种识别亚硫酸氢根的荧光探针及其制备方法和检测方法。
背景技术
二氧化硫(SO2)是人类生存环境中分布最广泛的大气污染物之一,对人类和其他生命体的健康具有极大的伤害。SO2同碳氢化合物、一氧化碳、氮氧化合物和颗粒物一起被公认为空气中对人类危害最大的五大污染物。作为有毒有害气体,能引起酸雨,进而破坏环境及生态系统。它能经叶面气孔进入植物内,经过呼吸系统进入人或动物体,然后与水反应分解为其衍生物亚硫酸盐(SO3 2-)以及亚硫酸氢盐(HSO3 -)。此外,由于亚硫酸根能防止细菌滋生、抑制酶和非酶的褐变,所以通常被应用到食品、药物、酒类中充当酶抑制剂、抗菌剂和食品添加剂。因此,开发一种高选择性、高灵敏度的方法用来检测二氧化硫及其衍生物是十分有意义的。
目前对二氧化硫及其衍生物的检测有多种方法,主要有滴定分析、色谱法、电化学法、毛细管电泳法、酶技术法和分光光度法等。但是这些方法普遍存在诸多的限制因素:样品前处理麻烦、检测工具的使操作复杂、成本较高且不适用于生物组织样品。然而与这些传统的检测手段相比较,荧光探针分析法则有操作简便、成本低、选择性高、灵敏度高、检测限低、生物相容性好等优点,使其能适用于生物体的成像及检测。设计合成选择性好、灵敏度高、检测限低和响应迅速的荧光探针具有十分重要的意义。
发明内容
本发明的目的在于,提供一种识别亚硫酸氢根的荧光探针及其制备方法和检测方法。本发明的荧光探针能够对亚硫酸氢根进行识别,且识别成本低,操作简单,结果可视,灵敏度高,选择性好。
本发明的技术方案:一种识别亚硫酸氢根的荧光探针,探针的分子式为:C44H66Br2N2,结构式如附图1所示。
一种前述的识别亚硫酸氢根的荧光探针的制备方法,包括如下步骤:
(1)将4-乙烯基吡啶、1,4-二溴-2,3,5,6-四甲基苯和醋酸钯加入三乙胺中混合,将混合物密封在N2氛围下的而高压反应瓶中,在100-120℃反应18-32h,得A品;
(2)将A品用二氯甲烷完全溶解成黑色悬液,得B品;
(3)将B品依次用水和饱和食盐水洗涤,得C品;
(4)将C品静置分层,将最下层的二氯甲烷层分离出来后,用无水硫酸镁干燥,旋干,最后用乙醇重结晶,得D品;
(5)将D品加入N,N-二甲基甲酰胺中溶解,然后加入1-溴癸烷,加热至75-85℃,反应20-36h,反应液中加入乙醚至其完全沉淀,抽滤,用乙醚洗涤两次,烘干,得到探针。
前述的识别亚硫酸氢根的荧光探针的制备方法,所述步骤(1)中,在每10mL三乙胺中加入150mg4-乙烯基吡啶、150mg的1,4-二溴-2,3,5,6-四甲基苯和30mg醋酸钯。
前述的识别亚硫酸氢根的荧光探针的制备方法,所述步骤(3)中,是将B品依次用水和饱和食盐水洗涤3次。
前述的识别亚硫酸氢根的荧光探针的制备方法,所述步骤(4)中,是采用无水乙醇进行重结晶。
前述的识别亚硫酸氢根的荧光探针的制备方法,所述步骤(5)中,所用D品和1-溴癸烷的物质的量之比为1:2,反应温度为80℃,反应时间为24h。
一种利用前述的识别亚硫酸氢根的荧光探针检测亚硫酸氢根的方法,是在水溶液中检测亚硫酸氢根。
前述的识别亚硫酸氢根的荧光探针检测亚硫酸氢根的方法,是将荧光探针溶于甲醇中,然后用二次水稀释,得荧光试剂,然后向试剂中滴入待识别样品,得样品溶液,对样品溶液进行荧光激发并测试分析荧光激发的荧光波长即可。
前述的识别亚硫酸氢根的荧光探针检测亚硫酸氢根的方法,所述荧光试剂中探针的浓度为10-5mol.L-1,所用荧光激发波长为348nm,当加入待识别样品并识别到亚硫酸氢根时,试剂的荧光最大发射波长由510nm红移至544nm。
本发明的有益效果
本发明的荧光探针能够对亚硫酸氢根进行识别检测,且检测过程成本低,操作简单,结果可以直接通过荧光变化看见,具有可视化的优点;另外,本发明的探针抗干扰能力强,具有检测灵敏度高,选择性好的优点。
为进一步说明本发明的有益效果,发明人做了如下实验:
一、定性分析测试
1、其特征标在于:在浓度范围为10-6~10-4mol/L的荧光探针水溶液中,当激发波长为348nm时,荧光探针的最大发射波长是510nm,当荧光探针水溶液中加入HSO3 -后,荧光探针的最大发射波长从510nm红移至544nm,表现为黄色荧光。
二、定量分析测试
1、荧光探针溶液的配制方法:称取7.082mg的探针,用甲醇溶解,配制成体积为10mL,浓度为1.0×10-3mol·L-1的溶液,取1个100.0mL容量瓶,将配置好的探针溶液取1mL于容量内,用二次水稀释到刻度线,得到浓度为1.0×10-5mol·L-1的探针溶液。
2、称取优级纯的硫氰酸钾盐配制成10mL水溶液,浓度都为1.0×10-1mol·L-1,根据需要用二次水逐级稀释。
3、取荧光试剂1.0×10-5mol·L-1标准液,往比色皿里加入3mL荧光试剂,分别滴加入1.0×10-1mol·L-1HSO3 -离子溶液,引入荧光光谱进行测定,激发波长为348nm。
4、分别以HSO3 -离子浓度为横坐标,荧光强度为纵坐标,得到工作曲线。
5、样品测定:取两个10.0mL容量瓶,分别加入荧光试剂1.0×10-3mol·L-10.1mL标准液,于两个容量中分别加入HSO3 -离子溶液,稀释至刻度,室温放置5分钟,引入3.0cm的石英比色皿进行荧光测定,根据荧光强度在工作曲线上查出样品浓度。检测识别的最低浓度值为9.234×10-8mol·L-1。
附图说明
图1为荧光探针分子的化学结构式;
图2为荧光探针分子的核磁氢谱图;
图3为荧光探针分子与不同阴离子作用的荧光光谱图;
图4为荧光探针分子在水中随着加入亚硫酸氢根后的荧光变化图;
图5为荧光探针分子检测亚硫酸氢根的检出限拟合图。
具体实施方式
下面结合实施例对本发明作进一步的说明,但并不作为对本发明限制的依据。
本发明的实施例
实施例1:一种识别亚硫酸氢根的荧光探针,分子式为:C44H66Br2N2,结构式如附图1所示。其制备方法如下:
(1)将4-乙烯基吡啶、1,4-二溴-2,3,5,6-四甲基苯和醋酸钯加入三乙胺中混合(每10mL三乙胺中加入150mg4-乙烯基吡啶、150mg的1,4-二溴-2,3,5,6-四甲基苯和30mg醋酸钯),将混合物密封在N2氛围下的而高压反应瓶中,在110℃反应25h,的A品;
(2)将A品用二氯甲烷完全溶解成黑色悬液,得B品;
(3)将B品依次用水和饱和食盐水洗涤3次,得C品;
(4)将C品静置分层,将最下层的二氯甲烷层分离出来后,用无水硫酸镁干燥,旋干,最后用无水乙醇重结晶,得D品;
(5)将D品加入N,N-二甲基甲酰胺中溶解,然后加入1-溴癸烷(D品和1-溴癸烷的物质的量之比为1:2),加热至80℃,反应24h,反应液中加入乙醚至其完全沉淀,抽滤,用乙醚洗涤两次,烘干,得到探针。
上述的识别亚硫酸氢根的荧光探针检测亚硫酸氢根的方法,是将荧光探针溶于甲醇中,然后用二次水稀释至浓度为10-5mol.L-1,得荧光试剂,然后向试剂中滴入待识别样品,得样品溶液,对样品溶液用波长为348nm荧光进行荧光激发,当加入待识别样品并识别到亚硫酸氢根时,试剂的荧光最大发射波长由510nm红移至544nm。
实施例2:一种识别亚硫酸氢根的荧光探针,分子式为:C44H66Br2N2,结构式如附图1所示。其制备方法如下:
(1)将4-乙烯基吡啶、1,4-二溴-2,3,5,6-四甲基苯和醋酸钯加入三乙胺中混合(每10mL三乙胺中加入150mg4-乙烯基吡啶、150mg的1,4-二溴-2,3,5,6-四甲基苯和30mg醋酸钯),将混合物密封在N2氛围下的而高压反应瓶中,在100℃反应32h,的A品;
(2)将A品用二氯甲烷完全溶解成黑色悬液,得B品;
(3)将B品依次用水和饱和食盐水洗涤3次,得C品;
(4)将C品静置分层,将最下层的二氯甲烷层分离出来后,用无水硫酸镁干燥,旋干,最后用无水乙醇重结晶,得D品;
(5)将D品加入N,N-二甲基甲酰胺中溶解,然后加入1-溴癸烷(D品和1-溴癸烷的物质的量之比为1:2),加热至75℃,反应36h,反应液中加入乙醚至其完全沉淀,抽滤,用乙醚洗涤两次,烘干,得到探针。
上述的识别亚硫酸氢根的荧光探针检测亚硫酸氢根的方法,是将荧光探针溶于甲醇中,然后用二次水稀释至浓度为10-5mol.L-1,得荧光试剂,然后向试剂中滴入待识别样品,得样品溶液,对样品溶液用波长为348nm荧光进行荧光激发,当加入待识别样品并识别到亚硫酸氢根时,试剂的荧光最大发射波长由510nm红移至544nm。
实施例3:一种识别亚硫酸氢根的荧光探针,分子式为:C44H66Br2N2,结构式如附图1所示。其制备方法如下:
(1)将4-乙烯基吡啶、1,4-二溴-2,3,5,6-四甲基苯和醋酸钯加入三乙胺中混合(每10mL三乙胺中加入150mg 4-乙烯基吡啶、150mg的1,4-二溴-2,3,5,6-四甲基苯和30mg醋酸钯),将混合物密封在N2氛围下的而高压反应瓶中,在120℃反应18h,的A品;
(2)将A品用二氯甲烷完全溶解成黑色悬液,得B品;
(3)将B品依次用水和饱和食盐水洗涤3次,得C品;
(4)将C品静置分层,将最下层的二氯甲烷层分离出来后,用无水硫酸镁干燥,旋干,最后用无水乙醇重结晶,得D品;
(5)将D品加入N,N-二甲基甲酰胺中溶解,然后加入1-溴癸烷(D品和1-溴癸烷的物质的量之比为1:2),加热至85℃,反应20h,反应液中加入乙醚至其完全沉淀,抽滤,用乙醚洗涤两次,烘干,得到探针。
上述的识别亚硫酸氢根的荧光探针检测亚硫酸氢根的方法,是将荧光探针溶于甲醇中,然后用二次水稀释至浓度为10-5mol.L-1,得荧光试剂,然后向试剂中滴入待识别样品,得样品溶液,对样品溶液用波长为348nm荧光进行荧光激发,当加入待识别样品并识别到亚硫酸氢根时,试剂的荧光最大发射波长由510nm红移至544nm。
以上所述,仅为本发明创造较佳的具体实施方式,但本发明创造的保护范围并不局限于此,任何熟悉本技术领域的技术人员在本发明创造揭露的技术范围内,根据本发明创造的技术方案及其发明构思加以等同替换或改变,都应涵盖在本发明创造的保护范围之内。
Claims (9)
2.一种根据权利要求1所述的识别亚硫酸氢根的荧光探针的制备方法,其特征在于,包括如下步骤:
(1)将4-乙烯基吡啶、1,4-二溴-2,3,5,6-四甲基苯和醋酸钯加入三乙胺中混合,将混合物密封在N2氛围下的而高压反应瓶中,在100-120℃反应18-32h,得A品;
(2)将A品用二氯甲烷完全溶解成黑色悬液,得B品;
(3)将B品依次用水和饱和食盐水洗涤,得C品;
(4)将C品静置分层,将最下层的二氯甲烷层分离出来后,用无水硫酸镁干燥,旋干,最后用乙醇重结晶,得D品;
(5)将D品加入N,N-二甲基甲酰胺中溶解,然后加入1-溴癸烷,加热至75-85℃,反应20-36h,反应液中加入乙醚至其完全沉淀,抽滤,用乙醚洗涤两次,烘干,得到探针。
3.根据权利要求2所述的识别亚硫酸氢根的荧光探针的制备方法,其特征在于:所述步骤(1)中,在每10mL三乙胺中加入150mg 4-乙烯基吡啶、150mg的1,4-二溴-2,3,5,6-四甲基苯和30mg醋酸钯。
4.根据权利要求2所述的识别亚硫酸氢根的荧光探针的制备方法,其特征在于:所述步骤(3)中,是将B品依次用水和饱和食盐水洗涤3次。
5.根据权利要求2所述的识别亚硫酸氢根的荧光探针的制备方法,其特征在于:所述步骤(4)中,是采用无水乙醇进行重结晶。
6.根据权利要求2所述的识别亚硫酸氢根的荧光探针的制备方法,其特征在于:所述步骤(5)中,所用D品和1-溴癸烷的物质的量之比为1:2,反应温度为80℃,反应时间为24h。
7.一种利用权利要求1所述的识别亚硫酸氢根的荧光探针检测亚硫酸氢根的方法,其特征在于:是在水溶液中检测亚硫酸氢根。
8.根据权利要求7所述的识别亚硫酸氢根的荧光探针检测亚硫酸氢根的方法,其特征在于:是将荧光探针溶于甲醇中,然后用二次水稀释,得荧光试剂,然后向试剂中滴入待识别样品,得样品溶液,对样品溶液进行荧光激发并测试分析荧光激发的荧光波长即可。
9.根据权利要求8所述的识别亚硫酸氢根的荧光探针检测亚硫酸氢根的方法,其特征标在于:所述荧光试剂中探针的浓度为10-5mol.L-1,所用荧光激发波长为348nm,当加入待识别样品并识别到亚硫酸氢根时,试剂的荧光最大发射波长由510nm红移至544nm。
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