CN110028515B - 一种氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物的制备及其应用 - Google Patents
一种氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物的制备及其应用 Download PDFInfo
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- CN110028515B CN110028515B CN201910382888.2A CN201910382888A CN110028515B CN 110028515 B CN110028515 B CN 110028515B CN 201910382888 A CN201910382888 A CN 201910382888A CN 110028515 B CN110028515 B CN 110028515B
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Abstract
本发明公开了一种氨酰甲基‑(2‑甲胺基呋喃)罗丹明酰胺衍生物的制备及其应用,属于无机材料合成与应用技术领域。该氨酰甲基‑(2‑甲胺基呋喃)罗丹明酰胺衍生物,是由罗丹明B与水合肼反应先制得罗丹明B酰肼,然后再分别与氯乙酰氯和2‑呋喃甲胺缩合反应制备而成。本发明合成的氨酰甲基‑(2‑甲胺基呋喃)罗丹明酰胺化合物是含内酯环结构的罗丹明类衍生物,具有激发和发射波长在可见光区、荧光量子产率高、摩尔消光系数大以及生物相容性好等特点,其制备方法简单,反应条件温和,产率较高,与铜离子结合后,裸眼识别效果好,响应迅速,专一选择性高,甚至可用于铜离子的实时在线微量检测,可发展成一种具有重要研究意义的光学传感材料。
Description
技术领域
本发明属于无机材料合成及应用技术领域,具体涉及一种简便制备罗丹明衍生物光学传感材料的制备方法及其应用。
背景技术
作为在各种生理过程中起关键作用,与人的健康紧密相关的软过渡金属之一,铜离子的含量低于体内铁和锌离子的含量,然而,过量的铜离子积累可能会导致严重的后果。例如,人体短期暴露于高浓度铜离子的环境中会引起胃肠不适,而长期暴露可导致肝、肾功能损害。研究表明,铜离子在人体内的异常积累还会引起许多神经退行性疾病,如威尔森氏病、阿尔茨海默病等。因此,识别和检测铜离子的含量具有重要的研究价值。目前,关于铜离子的直接检测的方法主要包括原子吸收光谱法、原子发射光谱法、光度分析法以及电感耦合等离子体质谱法等。其中设计新型的光学探针与客体之间相互结合引起其荧光或紫外可见光谱变化的光度分析法因为仪器设备简单价廉,能够高效、高灵敏度高和高选择性识别检测金属离子从而引起了生命科学、食品行业、环境保护以及药物学等领域科研工作者的广泛关注。
现有的铜离子光学识别分子探针化合物种类繁多,但仍然存在制备过程复杂,消耗试剂量大、响应灵敏度不高、选择性低、微量检测难等缺陷,所以近年来,咕吨类近红外荧光染料的一种罗丹明类化合物因为在长波长处表现出强吸收,并且拥有与金属离子作用后可发射出显著荧光的内酯型螺环状结构特征而常常被用作为金属离子响应“开关”。本专利正是基于罗丹明衍生物所表现出的特殊的光学效应和应用潜力,通过设计引入不同的官能团对罗丹明母体结构进行修饰,并采用合理、简单、条件温和的合成方法制备出结构刚性适当、量子产率高、生物相容性好、特异选择性强的罗丹明衍生物分子探针,从而开发出一类准确度和灵敏度更高,满足铜离子裸眼在线识别和微量检测所需要的新型光学传感材料。
发明内容
本发明的目的在于克服现有的铜离子比色和荧光分子探针制备原料昂贵,合成过程较为复杂,反应条件苛刻,提纯分离困难、光学传感灵敏度和选择性低等缺点,通过简单的反应,较为温和的反应条件,较高产率和纯度制备分离出分子结构中含共轭双键和较活泼助色基团的罗丹明衍生物分子探针,利用铜离子对该分子探针中罗丹明螺内酰胺的螯合诱导开环产生荧光和紫外光谱以及颜色的变化,从而裸眼、高灵敏度、单一选择性识别并检测铜离子。
为了实现上述目的,本发明是通过以下技术方案予以实现的。
本发明一种氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物的制备方法,具体包括以下步骤:
(1)称取2.40g(5.00mmol)罗丹明B置于烧瓶中加入60~70mL乙醇溶解,然后缓慢滴加5.0~7.0mL水合肼(质量百分含量98%),反应回流3~5h之后,蒸干溶剂后,残余溶剂用水溶解,调节pH至7.0左右,析出大量沉淀,将沉淀过滤干燥,即为罗丹明B酰肼。
(2)取1.438g(3.12mmol)的罗丹明B酰肼溶于60~70mL的二氯甲烷中,加入2.0~2.5mL的氯乙酰氯,并加入3.0~5.0mL的三乙胺作为缚酸剂,冰盐浴下快速搅拌反应10~15h,蒸除溶剂后,得到淡紫色固体粗产物,接着中性氧化铝过柱后得到黄白色固体。
罗丹明B酰肼与氯乙酰氯的摩尔比为1:4~1:5之间。
(3)将步骤(2)得到的中间产物0.80g(1.52mmol)溶于乙腈中,滴加过量的2-呋喃甲胺0.4~0.6mL,加入0.40~0.60g碳酸钾(4.0~6.0mmol)做催化剂,加热回流6~8h后,蒸干溶剂,用乙酸乙酯/水反复萃取3~5次,中性氧化铝过柱后,脱除溶剂后获得淡黄色氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物产物。
所述步骤(2)和步骤(3)中,当中性氧化铝过柱时,流动相为乙酸乙酯和石油醚,其体积比为1:1或1:1.5。
上述氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物可以作为分子探针在铜离子比色识别和检测中加以应用。
本发明的科学原理:
采用光稳定性好、长波吸收短波发射、荧光量子产率高、细胞穿透能力强和生物毒性小等特性的罗丹明化合物母体,经过基团修饰后,构建出结构新颖的罗丹明衍生物分子探针后研究对铜离子的响应,研究发现,铜离子与该分子探针作用后肉眼观察到体系的颜色迅速变化,荧光显著增强,因此可用于对铜离子的灵敏、快速及裸眼识别,同时还具有选择性高可微量检测的优势。
本发明与其它铜离子比色和荧光传感分子探针材料的合成方法和应用相比,具有以下技术效果:
1、本发明合成的氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺化合物是含内酯环结构的罗丹明类衍生物,具有激发和发射波长在可见光区、荧光量子产率高、摩尔消光系数大以及生物相容性好等特点。
2、本发明制备方法简单,反应条件温和,产率较高。
3、本发明合成的氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺化合物与铜离子结合后,裸眼识别效果好,响应迅速,专一选择性高,甚至可用于铜离子的实时在线微量检测,可发展成为一种具有重要研究意义的光学传感材料。
附图说明
图1为本发明氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物的合成以及对铜离子的识别过程。
图2为本发明实施例3制备的氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物溶液(5×10-6M)中逐渐加入不同量铜离子后的紫外可见滴定光谱图(A);分子探针在565nm处吸收峰的吸光度变化值与铜离子浓度之间的校正曲线(B)。
图3为本发明实施例3制备的氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物溶液与铜离子作用后的Benesi-Hildebrand图。
图4为本发明实施例3制备的氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物溶液与铜离子作用后的Job’s图。
图5为本发明实施例3制备的氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物溶液(5×10-6M)加入15倍当量的铜离子和其它离子后的紫外可见吸收光谱柱形图。
具体实施方式
本发明的实质特点和显著效果可以从下述的实施例中得以体现,但它们并不对本发明作任何限制,本领域的技术人员根据本发明的内容做出一些非本质的改进和调整,均属于本发明的保护范围。下面通过具体实施方式对本发明作进一步的说明,其中实施例中反应产物的核磁数据测试表征使用的是德国Bruker公司的型号为AVANCE-III 400MHz的核磁共振仪(TMS为内标);红外光谱测试表征采用美国Nicolet/Nexus-870FT-IR型红外光谱仪(KBr压片);使用美国Perkin Elmer LS55型荧光光谱仪和美国WinASPECT PLUS2000型紫外光谱仪分别测定荧光和紫外可见吸收光谱。
本发明所提供的一种可用于铜离子比色识别的罗丹明类衍生物的制备方法,其合成路线如图1所示。首先罗丹明B和水合肼在乙醇溶剂中加热回流,调节pH至7.0左右,析出大量沉淀,过滤干燥后制得罗丹明B酰肼;接着将罗丹明B酰肼溶于二氯甲烷中,加入氯乙酰氯和缚酸剂三乙胺,于冰盐浴下快速搅拌反应一段时间,得淡紫色固体粗产物,过中性氧化铝(流动相为乙酸乙酯和石油醚)柱后得到黄白色固体;最后将该中间产物溶于乙腈中,滴加过量的2-呋喃甲胺和并催化剂碳酸钾,加热回流反应一段时间后,蒸除溶剂,用乙酸乙酯/水反复萃取并进入中性氧化铝(流动相为乙酸乙酯和石油醚)柱后,脱除溶剂制得淡黄色氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物产物。
一、本发明新型罗丹明类发光化合物的制备
实施例1
(1)称取2.40g(5.00mmol)罗丹明B置于烧瓶中加入65mL乙醇溶解,然后缓慢滴加5.0mL水合肼(质量百分含量98%),反应回流3h之后,蒸干溶剂后,残余溶剂用水溶解,调节pH至7.0左右,析出大量沉淀,将沉淀过滤干燥,即为罗丹明B酰肼。
(2)称取1.438g(3.12mmol)的罗丹明B酰肼溶于60mL的二氯甲烷中,加入2.0mL(12.50mmol)的氯乙酰氯,并加入3.0mL的三乙胺作为缚酸剂,冰盐浴下快速搅拌反应10h,蒸除溶剂后,得到淡紫色固体粗产物,接着中性氧化铝过柱后得到黄白色固体。
罗丹明B酰肼与氯乙酰氯的摩尔比为1:4。
中性氧化铝过柱时,流动相中乙酸乙酯和石油醚的体积比为1:1。
(3)将步骤(2)得到的中间产物称取0.80g(1.52mmol)溶于乙腈中,滴加过量的2-呋喃甲胺0.4mL,加入0.40g碳酸钾(4.0mmol)做催化剂,加热回流6h后,蒸干溶剂,用乙酸乙酯/水反复萃取3次,中性氧化铝过柱后,脱除溶剂后获得淡黄色氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物产物。
中性氧化铝过柱时,流动相中乙酸乙酯和石油醚的体积比为1:1。
实施例2
(1)称取2.40g(5.00mmol)罗丹明B置于烧瓶中加入70mL乙醇溶解,然后缓慢滴加6.0mL水合肼(质量百分含量98%),反应回流3h之后,蒸干溶剂后,残余溶剂用水溶解,调节pH至7.0左右,析出大量沉淀,将沉淀过滤干燥,即为罗丹明B酰肼。
(2)称取1.438g(3.12mmol)的罗丹明B酰肼溶于65mL的二氯甲烷中,加入2.25mL(14.06mmol))的氯乙酰氯,并加入3.5mL的三乙胺作为缚酸剂,冰盐浴下快速搅拌反应11h,蒸除溶剂后,得到淡紫色固体粗产物,接着中性氧化铝过柱后得到黄白色固体。
罗丹明B酰肼与氯乙酰氯的摩尔比为1:4.5。
中性氧化铝过柱时,流动相中乙酸乙酯和石油醚的体积比为1:1。
(3)将步骤(2)得到的中间产物称取0.80g(1.52mmol)溶于乙腈中,滴加过量的2-呋喃甲胺0.4mL,加入0.40g碳酸钾(4.0mmol)做催化剂,加热回流7h后,蒸干溶剂,用乙酸乙酯/水反复萃取4次,中性氧化铝过柱后,脱除溶剂后获得淡黄色氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物产物。
中性氧化铝过柱时,流动相中乙酸乙酯和石油醚的体积比为1:1。
实施例3
(1)称取2.40g(5.00mmol)罗丹明B置于烧瓶中加入60mL乙醇溶解,然后缓慢滴加6.0mL水合肼(质量百分含量98%),反应回流4h之后,蒸干溶剂后,残余溶剂用水溶解,调节pH至7.0左右,析出大量沉淀,将沉淀过滤干燥,即为罗丹明B酰肼。
(2)称取1.438g(3.12mmol)的罗丹明B酰肼溶于60mL的二氯甲烷中,加入2.0mL(12.50mmol)的氯乙酰氯,并加入4.0mL的三乙胺作为缚酸剂,冰盐浴下快速搅拌反应12h,蒸除溶剂后,得到淡紫色固体粗产物,接着中性氧化铝过柱后得到黄白色固体。
罗丹明B酰肼与氯乙酰氯的摩尔比为1:4。
中性氧化铝过柱时,流动相中乙酸乙酯和石油醚的体积比为1:1。
(3)将步骤(2)得到的中间产物称取0.80g(1.52mmol)溶于乙腈中,滴加过量的2-呋喃甲胺0.50mL,加入0.50g碳酸钾(5.00mmol)做催化剂,加热回流8h后,蒸干溶剂,用乙酸乙酯/水反复萃取3次,中性氧化铝过柱后,脱除溶剂后获得淡黄色氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物产物。
中性氧化铝过柱时,流动相中乙酸乙酯和石油醚的体积比为1:1。
实施例4
(1)称取2.40g(5.00mmol)罗丹明B置于烧瓶中加入60mL乙醇溶解,然后缓慢滴加7.0mL水合肼(质量百分含量98%),反应回流5h之后,蒸干溶剂后,残余溶剂用水溶解,调节pH至7.0左右,析出大量沉淀,将沉淀过滤干燥,即为罗丹明B酰肼。
(2)称取1.438g(3.12mmol)的罗丹明B酰肼溶于60mL的二氯甲烷中,加入2.25mL(14.06mmol)的氯乙酰氯,并加入4.0mL的三乙胺作为缚酸剂,冰盐浴下快速搅拌反应13h,蒸除溶剂后,得到淡紫色固体粗产物,接着中性氧化铝过柱后得到黄白色固体。
罗丹明B酰肼与氯乙酰氯的摩尔比为1:4.5。
中性氧化铝过柱时,流动相中乙酸乙酯和石油醚的体积比为1:1。
(3)将步骤(2)得到的中间产物称取0.80g(1.52mmol)溶于乙腈中,滴加过量的2-呋喃甲胺0.5mL,加入0.5g碳酸钾(5.0mmol)做催化剂,加热回流6h后,蒸干溶剂,用乙酸乙酯/水反复萃取4次,中性氧化铝过柱后,脱除溶剂后获得淡黄色氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物产物。
中性氧化铝过柱时,流动相中乙酸乙酯和石油醚的体积比为1:1。
实施例5
(1)称取2.40g(5.00mmol)罗丹明B置于烧瓶中加入70mL乙醇溶解,然后缓慢滴加7.0mL水合肼(质量百分含量98%),反应回流5h之后,蒸干溶剂后,残余溶剂用水溶解,调节pH至7.0左右,析出大量沉淀,将沉淀过滤干燥,即为罗丹明B酰肼。
(2)称取1.438g(3.12mmol)的罗丹明B酰肼溶于60~70mL的二氯甲烷中,加入2.5mL(15.625mmol)的氯乙酰氯,并加入5.0mL的三乙胺作为缚酸剂,冰盐浴下快速搅拌反应15h,蒸除溶剂后,得到淡紫色固体粗产物,接着中性氧化铝过柱后得到黄白色固体。
罗丹明B酰肼与氯乙酰氯的摩尔比为1:5。
中性氧化铝过柱时,流动相中乙酸乙酯和石油醚的体积比为1:1.5。
(3)将步骤(2)得到的中间产物称取0.80g(1.52mmol)溶于乙腈中,滴加过量的2-呋喃甲胺0.5mL,加入0.50g碳酸钾(5.0mmol)做催化剂,加热回流7h后,蒸干溶剂,用乙酸乙酯/水反复萃取3次,中性氧化铝过柱后,脱除溶剂后获得淡黄色氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物产物。
中性氧化铝过柱时,流动相中乙酸乙酯和石油醚的体积比为1:1。
实施例6
(1)称取2.40g(5.00mmol)罗丹明B置于烧瓶中加入70mL乙醇溶解,然后缓慢滴加7.0mL水合肼(质量百分含量98%),反应回流5h之后,蒸干溶剂后,残余溶剂用水溶解,调节pH至7.0左右,析出大量沉淀,将沉淀过滤干燥,即为罗丹明B酰肼。
(2)称取1.438g(3.12mmol)的罗丹明B酰肼溶于70mL的二氯甲烷中,加入2.0mL(12.50mmol)的氯乙酰氯,并加入4.0mL的三乙胺作为缚酸剂,冰盐浴下快速搅拌反应12h,蒸除溶剂后,得到淡紫色固体粗产物,接着中性氧化铝过柱后得到黄白色固体。
罗丹明B酰肼与氯乙酰氯的摩尔比为1:4。
中性氧化铝过柱时,流动相中乙酸乙酯和石油醚的体积比为1:1.5。
(3)将步骤(2)得到的中间产物称取0.80g(1.52mmol)溶于乙腈中,滴加过量的2-呋喃甲胺0.6mL,加入0.60g碳酸钾(6.0mmol)做催化剂,加热回流8h后,蒸干溶剂,用乙酸乙酯/水反复萃取5次,中性氧化铝过柱后,脱除溶剂后获得淡黄色氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物产物。
中性氧化铝过柱时,流动相中乙酸乙酯和石油醚的体积比为1:1.5。
目标产物表征:产率:53%。1H NMR(400MHz,DMSO-d6):,7.76(t,J=8Hz,1H),7.46(t,J=8Hz,2H),6.98(m,J=8Hz,1H),6.41(s,1H),6.37(s,3H),6.23(s,4H),3.07(s,1H),2.74(s,1H),2.73(s,1H),2.70(s,1H),3.34(s,2H),3.31(d,J=8Hz,6H),1.29(s,1H),1.25(s,1H),1.22(s,1H),1.08(t,J=12Hz,16H);(KBr,cm-1):1620(C=O),1510(C-N),1220(C-O-C),1120(C-O-C)。
二、本发明罗丹明衍生物对铜离子的比色识别和检测效果评价
以最佳实施例3制备的氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物为分子探针,研究对铜离子的光学传感响应效果。
(1)经过研究发现,向氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物的二甲基甲酰胺溶液中加入铜离子,溶液的颜色会在2s之内由无色迅速地转变为深红色(图略),而且在10min之内没有任何下降的趋势,表明该化合物可用于肉眼快速简捷地识别铜离子并且稳定性较好。
(2)采用紫外可见光谱仪研究了铜离子加入氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物的乙腈水溶液后的光谱变化,如图2A所示,可以观察到体系中分子探针在565nm处的吸收峰逐渐增强,当铜离子的浓度达到95μM时,紫外吸收峰几乎达到饱和。这可能是由于铜离子与氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物之间发生配位作用,产生金属配体电荷转移作用(MLCT)从而导致分子探针化合物的紫外可见光谱发生显著的变化。根据紫外滴定曲线,可以获知565nm处新生成吸收峰的吸光度差值与铜离子浓度在1~90μM之间呈良好的线性关系,检测限为0.32μM(信噪比为3,r=0.9980)(如图2B),这表明氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物可用于铜离子的微量检测。
(3)使用修正后的Benesi-Hildebrand方程(Singh T S,Paul P C,Pramanik H AR.Fluorescent chemosensor based on sensitive Schiff base for selectivedetection of Zn2+.Spectrochim.Acta A.2014,121:520-526.)计算分子探针氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物与铜离子的配位结合常数(其中A0为分子探针在565nm处的吸光度,A为在加入特定浓度铜离子后的吸光度,M为铜离子浓度)为6.505×102M-1,该理论值表明氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物对铜离子有较强的结合能力(如图3)。进一步采用Job’s曲线计算出(Li Z,Zhou Y,Yin K,Yu Z,LiY.J.Ren.A new fluorescence“turn-on”type chemosensor for Fe3+based onnaphthalimide and coumarin.Dyes Pigments,2014,105:7-11)(取浓度均为1m M的探针与铜离子溶液,保持总体积为50μL)氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物与铜离子之间的配位比,结果表明当铜离子与探针的摩尔分数均为0.5时,紫外吸收峰强度达到峰值,可以得出铜离子与该探针之间以1:1的形式进行配位(如图4)。
(4)光学分子探针的实际应用取决于对目标分子的选择性识别,因此采用紫外可见光谱仪研究了其它可能共存的离子对氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物识别铜离子溶液的影响,如图5所示。在含有5μM探针分子的乙腈和水(V乙腈:V水=1:1)混合溶液中,加入15倍当量的金属离子,对探针进行选择性测试,结果表明该分子探针除了对汞离子有轻微响应之外,其它金属离子如钠离子、镁离子、钾离子、铝离子、铁离子、亚铁离子、铬离子、镉离子、锌离子以及银离子与探针作用后紫外可见光谱峰强度无明显变化,从而证实该分子探针对铜离子的识别选择性较高。
Claims (4)
1.一种氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物的制备方法,其特征在于包括以下步骤:
(1)称取2.40g罗丹明B置于烧瓶中加入60~70mL乙醇溶解,然后缓慢滴加5.0~7.0mL质量百分含量为98%的水合肼,反应回流3~5h之后,蒸干溶剂后,残余溶剂用水溶解,调节pH至7.0左右,析出大量沉淀,将沉淀过滤干燥,即为罗丹明B酰肼;
(2)取步骤(1)制备的1.438g的罗丹明B酰肼溶于60~70mL的二氯甲烷中,加入2.0~2.5mL的氯乙酰氯,并加入3.0~5.0mL的三乙胺作为缚酸剂,冰盐浴下快速搅拌反应10~15h,蒸除溶剂后,得到淡紫色固体粗产物,接着中性氧化铝过柱后得到黄白色固体;
所述罗丹明B酰肼与氯乙酰氯的摩尔比为1:4~5;
(3)将步骤(2)得到的黄白色固体0.80g溶于乙腈中,滴加过量的2-呋喃甲胺0.4~0.6mL,加入0.40~0.60g碳酸钾做催化剂,加热回流6~8h后,蒸干溶剂,用乙酸乙酯/水反复萃取3~5次,中性氧化铝过柱后,脱除溶剂后获得氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物产物。
2.如权利要求1所述的一种氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物的制备方法,其特征在于:所述步骤(2)和步骤(3)中,当中性氧化铝过柱时,流动相为乙酸乙酯和石油醚。
3.如权利要求2所述的一种氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物的制备方法,其特征在于:所述乙酸乙酯和石油醚的体积比为1:1或1:1.5。
4.如权利要求1所述方法制备的氨酰甲基-(2-甲胺基呋喃)罗丹明酰胺衍生物作为光学分子探针在非诊断非治疗目的的铜离子比色识别和检测中的应用。
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