CN108219774A - 一种吡啶并[1,2-a]苯并咪唑取代的喹啉类检测次氯酸的荧光探针及其应用 - Google Patents
一种吡啶并[1,2-a]苯并咪唑取代的喹啉类检测次氯酸的荧光探针及其应用 Download PDFInfo
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Abstract
本发明公开了一种1‑乙基‑4‑(2‑(4‑苯基吡啶并[1,2‑a]苯并咪唑)乙烯基)喹啉‑1‑碘化物的分子荧光探针,其化学结构如式(1)所示。本发明的荧光探针在乙醇/水(体积比2:8)溶液中对次氯酸有好的荧光选择性、较高的灵敏度,有广阔的应用前景。
Description
背景技术
次氯酸作为活性氧化剂在日常生活中的应用非常广泛,如作为消毒剂用于日常的清洁,作为漂白剂用于工业、纺织业等行业。在生物体细胞中,次氯酸根离子在过氧化氢酶的催化下参与了许多重要的生理病理过程。在维持细胞内的氧化还原的平衡状态起到了重要的作用。正常状态下,一定浓度的次氯酸对生物体组织的修复、疾病的防御等是有益的,但是一旦细胞内次氯酸的浓度发生异常,就会导致一系列疾病的发生,如:关节炎、动脉粥样硬化、心血管疾病甚至癌症等。因此能够有效的检测环境及生物体中次氯酸浓度的变化已经成为一项重大的研究方向及课题。
有机小分子荧光探针检测方法以高灵敏度、高选择性、操作简单实用性强等优点被科学家们广泛关注并且积极应用。目前用荧光探针检测法来检测次氯酸是检测次氯酸根离子较为广泛的方法之一,但用于荧光探针的荧光团种类较少,主要是香豆素、罗丹明、1,8-萘二甲基酰亚胺等,需要发现新的荧光团来进行检测。
发明内容
对于上述情况,本发明的目的之一是提供一种合成简单,反应条件温和,成本较低的一种荧光探针的合成,目的二是提供一种新的荧光团来进行荧光检测,目的三是提供一种选择性好,灵敏度高的荧光探针来检测次氯酸根离子。
本发明的设计方案是:一种1 -乙基-4-(2-(4- 苯基吡啶并[1,2-a] 苯并咪唑)乙烯基)喹啉-1-碘化物荧光探针,用于检测次氯酸根例子,化学结构式如本式所示:
(1)
本发明主要是提供一种检测次氯酸的分子荧光探针,即1 -乙基-4-(2-(4- 苯基吡啶并[1,2-a] 苯并咪唑)乙烯基)喹啉-1-碘化物探针的应用,式(1)化合物在乙醇/水溶液中(体积比2:8)有特异的荧光选择性。
本发明还包括1 -乙基-4-(2-(4- 苯基吡啶并[1,2-a] 苯并咪唑)乙烯基)喹啉-1-碘化物荧光探针的合成方法,在乙醇溶液中4-苯基-吡啶并[1,2-a]苯并咪唑-3-甲醛与4-甲基-1-乙基喹啉-1-碘化物按照摩尔比1:1.5投料比例,加热回流12h,式(1)即为化合物。
配置式(1)化合物的乙醇/水(体积比2:8)溶液,分别加入10当量的NaCl、MgCl2·6H2O、Zn(CH3COO)2、FeCl3·6H2O、CuCl2、HO.、t-BuO·、KO2、1O2、NaOONO2、H2O2、t-BuOOH、HClO的水溶液,通过荧光光谱测试来研究对不同离子的选择性,测其荧光发射波谱强度变化发现:本发明所述的1 -乙基-4-(2-(4- 苯基吡啶并[1,2-a] 苯并咪唑)乙烯基)喹啉-1-碘化物荧光探针即式(1)化合物对次氯酸有独特的荧光选择性,如图1所示。逐渐加入次氯酸至1.5倍当量后,化合物1在504nm处荧光强度明显增强。1 -乙基-4-(2-(4- 苯基吡啶并[1,2-a]苯并咪唑)乙烯基)喹啉-1-碘化物分子荧光探针即式(1)化合物作为检测次氯酸的荧光探针具有较为明显的现象。
本发明提供了一种分子荧光探针即式(1)化合物,本实验证明本发明所述式(1)化合物可与次氯酸在乙醇/水(体积比2:8)溶液中以化学计量比1:1.5反应,在反应过程中,由于式(1)化合物在加入次氯酸后,水解氧化成酸,使得荧光强度增强。因此可以证明本发明所述的式(1)化合物在乙醇/水(体积比为2:8)中对次氯酸有独特的荧光选择性以及较高的灵敏度。
附图说明
图1:式(1)化合物(5×10-6M)的乙醇/水(体积比2:8)溶液中加入10当量的不同离子的荧光强度变化图。
图2:式(1)化合物(5×10-6M)的乙醇/水(体积比2:8)溶液中进行ClO-荧光滴定图。图中FL Intensity为荧光强度,Wavelength为波长,equ.为倍数。
图3:式(5×10-6M)的乙醇/水(体积比2:8)溶液中对ClO-反应的时间。
图4是式(1)化合物合成方法反应式图。
具体实施方式
实施例1:式(1)化合物合成方案如下是所示:
具体合成步骤如下:
在25 mL圆底烧瓶中依次加入0.1 g(0.36 mmol)(4-(二乙氨基)-2-羟基苯甲酰基)苯甲醛,0.17 g(0.55 mmol) 乙基噻唑, 20 mL乙醇,加热回流反应12小时。TLC检测反应完成,冷却析出大量结晶,洗涤,对溶液进行浓缩,柱层析得到0.13 g黑红色固体,产率59% 。
核磁共振氢谱测定:1H NMR(400MHz,CDCl3):δ 9.19 (d, 1H), 8.39 (d, 2H),8.28 (m, 2H), 8.13 (s, 1H), 8.01 (d, 1H), 7.85 (m, 3H), 7.77 (t, 1H), 7.64(s, 5H), 7.49 (d, 2H), 5.13 (q, 2H), 4.01 (q, 1H), 3.23 (d, 1H), 1.66 – 1.49(m, 3H).
实施例2
向式(1)化合物(5×10-6M)的乙醇/水(体积比2:8)溶液,分别加入10当量的NaCl、MgCl2·6H2O、Zn(CH3COO)2、FeCl3·6H2O、CuCl2、HO.、t-BuO·、KO2、1O2、NaOONO2、H2O2、t-BuOOH、HClO后,测其在504nm荧光强度的变化,显示化合物对次氯酸具有的ClO-后,化合物1在504nm处荧光强度明显增强。如图2所示。
实施例3
向式(1)化合物(5×10-6M)的乙醇/水(体积比2:8)溶液,分别加入0、1.5倍当量的ClO-后,测其反应时间的快慢。如图3所示。
Claims (2)
1.一种种吡啶并[1,2-a]苯并咪唑取代的喹啉类检测次氯酸的荧光探针即1 -乙基-4-(2-(4- 苯基吡啶并[1,2-a] 苯并咪唑)乙烯基)喹啉-1-碘化物的荧光探针,其化学结构式如式(1)所示:
式(1)化合物在乙醇/水溶液中(体积比2:8)对次氯酸有独特的荧光选择性。
2.权利要求1所述中1 -乙基-4-(2-(4- 苯基吡啶并[1,2-a] 苯并咪唑)乙烯基)喹啉-1-碘化物荧光探针的合成方法,其特征在于:在乙醇溶液中,将4-苯基-吡啶并[1,2-a]苯并咪唑-3-甲醛与4-甲基-1-乙基喹啉-1-碘化物按照摩尔比1:1.5投料比例,加热回流12h,得到1 -乙基-4-(2-(4- 苯基吡啶并[1,2-a] 苯并咪唑)乙烯基)喹啉-1-碘化物。
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CN112538051B (zh) * | 2020-12-17 | 2022-03-22 | 桂林理工大学 | 一种用于氟乐灵检测的苯并咪唑荧光探针及其合成方法 |
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