CN110156679B - 一种喹啉衍生物荧光探针及其制备方法和用途 - Google Patents
一种喹啉衍生物荧光探针及其制备方法和用途 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及一种水中检测铋离子的荧光探针,具体地说是一种喹啉衍生物荧光探针及其制备方法和用途。
背景技术
金属离子荧光探针因在环境及生物化学领域的广泛应用而受到关注。铋在元素周期表中处在金属和非金属的交界线,具有独特的理化性质,被称为“绿色金属”。铋化合物广泛应用于日常生活、显示材料和医药制剂中,并被用作抗菌、抗艾滋/病毒和放射治疗药物。它们还广泛用于治疗梅毒、幽门螺杆菌引起的胃炎和皮肤病。铋也被用于乳霜和染发剂的制备。此外,在近几十年,铋在材料领域的应用也受到了广泛关注。例如,将掺有铋的荧光材料应用于LEDs中。然而,铋易蓄积在人体内的肾脏中,若蓄积浓度过高,则会产生肾脏和中枢神经***的毒性反应。因此,检测水中铋含量势在必行。
近年来,各种铋的检测方法不断发展,包括液相萃取法、氢化物发生电感耦合等离子体法(ICP)、电热汽化ICP质谱法、原子吸收光谱法、电位溶出分析、阳极溶出伏安法和阴极溶出伏安法。然而,这些方法中的大多数都面临着高昂的成本、耗时且受控的反应条件。因此,通常使用具有高选择性、高灵敏度、低检测限、操作简单等优点的荧光检测方法监测水溶液中的Bi3+离子。
喹啉衍生物是一类重要的含氮杂环化合物。因其在光学、药理和生物方面的突出表现,而广泛应用于医药、食品、材料、农药等领域。因此,利用喹啉特殊的性质合成出新的具有潜在应用价值的高灵敏度的荧光分子探针用于检测水中铋离子是非常有意义的。
发明人对本申请的相关内容作了如下检索:
http://apps.webofknowledge.com/UA_GeneralSearch_input.do?product=UA&search_mode=GeneralSearch&SID=6DKJFWoApWtYGpFOFdO&preferencesSaved=网检索结果:(2019/5/28)
中国知网检索结果:(2019/5/28)
检索方式一:
篇名-----喹啉衍生物铋离子荧光探针-----无。
篇名-----喹啉衍生物铋离子荧光响应材料-----无。
篇名-----喹啉衍生物铋离子响应材料-----5项,均与目标化合物无关。
篇名-----铋离子荧光探针-----无。
篇名-----水中铋离子检测-----无。
检索方式二:
全文------喹啉衍生物铋离子荧光探针6项,均与目标化合物无关。
全文------喹啉衍生物铋离子荧光材料16项,均与目标化合物无关。
全文------喹啉衍生物铋离子响应材料28项,均与目标化合物无关。
全文------铋离子荧光探针36项,均与目标化合物无关。
全文------水中铋离子检测403项,均与目标化合物无关。
检索方式三:
关键词-----喹啉衍生物铋离子荧光探针无相关文献。
关键词-----喹啉衍生物铋离子荧光响应材料无相关文献。
关键词-----喹啉衍生物铋离子响应材料无相关文献。
关键词-----铋离子荧光探针无相关文献。
关键词-----水中铋离子检测无相关文献。
发明内容
本发明旨在提供一种喹啉衍生物荧光探针及其制备方法和用途,利用knoevenagel缩合反应形成的π桥将2-甲基-4-氨基-1-丁基喹啉鎓溴盐(Q)与N-甲基-N-羟乙基氨基苯甲醛(L)连接起来,形成大π共轭体系,优化材料光学性能,在水中高效选择性地检测铋离子。
喹啉盐具有较好的刚性平面、稳定性、良好的吸电子能力及一定的水溶性。N-甲基-N-羟乙基氨基苯甲醛中有N、O原子作为反应的作用位点,易于与多种金属离子或生物分子形成配位键或氢键。采用喹啉盐与N-甲基-N-羟乙基氨基苯甲醛进行knoevenagel缩合,有效地扩大电子的离域范围,改善了紫外吸收及荧光发射性能,提高材料在水中的对Bi3+离子专一性识别。
本发明喹啉衍生物荧光探针,简记为Q-L荧光探针,其结构如下:
本发明喹啉衍生物荧光探针的制备方法,包括如下步骤:
将2-甲基-4-氨基-1-丁基喹啉鎓溴盐0.89g(3mmol)、N-甲基-N-羟乙基氨基苯甲醛1.08g(6mmol)、100μL哌啶和30mL甲醇置于50mL圆底烧瓶中,加热回流反应8h;反应结束后冷却至室温,加入20mL四氢呋喃,析出橙红色固体,抽滤,经30mL四氢呋喃洗涤,无水NaSO4干燥,柱层析提纯(甲醇:二氯甲烷=1:12,v/v),得到目标产物Q-L荧光探针,产率45%。
本发明喹啉衍生物荧光探针的用途,是在水中检测铋离子时作为检测试剂应用,检测限为1.44×10-6M。
本发明以2-甲基-4-氨基-1-丁基喹啉鎓溴盐(Q)与N-甲基-N-羟乙基氨基苯甲醛(L)为原料,通过knoevenagel缩合反应,简洁高效地制备了喹啉衍生物Q-L荧光探针。该荧光探针对铋离子有高效的选择性,基于荧光探针Q-L识别能力,发明人对其进行水中检测铋离子研究。
实验发现,Q-L荧光发射峰位于465nm,随铋离子含量的增加,可在465nm处检测到增强的荧光信号。这一研究结果的发现,对喹啉衍生物荧光探针的设计、制备和水中对金属离子的识别具有重要意义。
与已有技术相比,本发明的有益效果体现在:
1、本发明Q-L具有高效的选择性识别Bi3+,可用于水中检测,具有明显的应用价值。
2、本发明Q-L在水中检测Bi3+,随Bi3+含量的增加,可检测到增强的荧光发射信号,具有实际应用价值。
3、本发明制备Q-L,步骤简单,节能减排。
附图说明
图1是Q-L的核磁共振氢谱图。从图1中可以看出,1H NMR(CD3SOCD3,400MHz)δ(ppm):8.66(s,2H),8.45(d,J=7.2Hz,1H),8.17(d,J=5.2Hz,1H),8.01(t,J=7.2Hz,1H),7.71(t,J=8.0Hz,1H),7.64(d,8.8Hz,2H),7.45(d,J=15.6Hz,1H),7.27(d,J=15.6Hz,1H),7.11(s,1H),6.79(d,J=8.8Hz,2H),4.64(t,J=8.0Hz,2H),3.59(t,J=6.4Hz,2H),3.50(t,J=5.6Hz,2H),1.47(q,J=7.2Hz,2H),0.96(t,J=7.6Hz,3H).
图2是Q-L的质谱图。从图2中可以看出,液相色谱质谱联用仪测得Q-L分子量为376.23。
图3是Q-L的红外光谱图。从图2中可以看出,FT-IR(KBr,cm-1)ν:3310,3127,2944,2862,1648,1583,1548,1525,1465,1379,1182,1047,953,800,746,622,540。
图4是Q-L对不同离子的识别相对荧光强度图。从图4可以看出,Q-L对铋离子有识别作用,其它各种金属离子基本不干扰Q-L对铋离子识别。
图5是Bi3+对Q-L的荧光滴定光谱及Q-L浓度与相对荧光强度关系图。从图5可以看出,随Bi3+浓度的增加,荧光发射峰位在465nm处的荧光强度逐渐增强,当Bi3+的浓度达到30μM。荧光强度达到最强。在Bi3+浓度在0-10μM之间时,加入的Bi3+浓度与荧光强度成线性关系,Q-L对Bi3+的检测限为1.44×10-6M。
具体实施方式
1、Q-L荧光探针的制备
将2-甲基-4-氨基-1-丁基喹啉鎓溴盐0.89g(3mmol)、N-甲基-N-羟乙基氨基苯甲醛1.08g(6mmol)、100μL和30mL甲醇置于50mL圆底烧瓶中,加热回流8h,冷却至室温,加入20mL四氢呋喃,析出橙红色固体,抽滤,经30mL四氢呋喃洗涤,甲醇溶解,无水NaSO4干燥,柱层析提纯(V甲醇:V二氯甲烷=1:12),得到目标产物Q-L荧光探针,产率45%。
1H NMR(CD3SOCD3,400MHz)δ(ppm):8.66(s,2H),8.45(d,J=7.2Hz,1H),8.17(d,J=5.2Hz,1H),8.01(t,J=7.2Hz,1H),7.71(t,J=8.0Hz,1H),7.64(d,8.8Hz,2H),7.45(d,J=15.6Hz,1H),7.27(d,J=15.6Hz,1H),7.11(s,1H),6.79(d,J=8.8Hz,2H),4.64(t,J=8.0Hz,2H),3.59(t,J=6.4Hz,2H),3.50(t,J=5.6Hz,2H),1.47(q,J=7.2Hz,2H),0.96(t,J=7.6Hz,3H).FT-IR(KBr,cm-1)ν:3310,3127,2944,2862,1648,1583,1548,1525,1465,1379,1182,1047,953,800,746,622,540.Q-L理论分子量为:376.24,液相色谱质谱联用仪测得Q-L分子量为:376.23.
2、Q-L对铋离子的识别
选择性行为是荧光探针的最重要特征之一。如图4所示,当加入和Q-L相等量的金属离子,如:Na+,K+,Cu2+,Mn2+,Mg2+,Ni2+,Eu3+,Ca2+,Hg2+,Pb+,Cd2+,Zn2+,Fe3+,Ba2+,Al3+,Co2+,Bi3+时,只有加入铋离子的Q-L在水中的荧光发射峰位在465nm处荧光强度明显增强,其他金属离子却没有明显改变。干扰试验显示,其它各种金属离子基本不干扰Q-L对铋离子识别。
3、Q-L在水中响应铋离子的灵敏度研究
Bi3+对Q-L的荧光滴定光谱见图4图5。由图5可知,在10μM的Q-L水溶液中加入不同浓度的Bi3+,随Bi3+浓度的增加,荧光发射峰位在465nm处的荧光强度逐渐增强,当Bi3+的浓度达到30μM。荧光强度达到最强。由图5,Q-L浓度与相对荧光强度关系图可知,在Bi3+浓度在0-10μM之间时,加入的Bi3+浓度与荧光强度成线性关系,相关系数为0.999,根据计算公式3δ/S(δ为标准偏差,S为校正曲线斜率),计算得出化合物Q-L对Bi3+的检测限为1.44×10-6M。
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