CN106565768A - 一种苯并咪唑并苯并异喹啉酮硅醚的制备方法及其应用 - Google Patents
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Abstract
本发明公开了一种反应型氟离子分子探针的制备方法。其特征是以1,8‑萘二甲酸酐、2,3‑二氨基苯酚、叔丁基二苯基氯硅烷为原料制备的一种基于苯并咪唑并苯并异喹啉酮‑12‑硅醚的新型氟离子检测探针。该分子探针具有合成简便,反应条件温和,易于纯化和光学性能稳定等优点。本发明的探针分子可以在DMSO介质中通过与氟离子的特异性反应,使分子探针中的氧硅键(R‑O‑Si)发生断裂,转变为氧负离子(R‑O‑),最大吸收波长发生红移(225 nm),颜色由黄色转变为蓝色,裸眼可以清晰辨别颜色的变化,其吸收强度与氟离子的浓度具有良好的线性关系。同时表现出对氟离子的高度选择性,不受其他阴离子的干扰,并且响应速度快。该探针分子在生物医药化学、环境科学等领域都具有重要的实际应用价值。
Description
技术领域
本发明涉及环境分析、生物分析检测技术领域,具体涉及一种反应型氟离子分子探针的制备方法和该分子探针在检测氟离子方面的应用。
背景技术
阴离子在很多化学和生物进程中扮演着重要的角色,因此近来年阴离子的识别和检测受到了极大的关注。其中,氟离子的识别和检测尤为重要。氟是人体所必需的微量元素,适量的氟化物摄入可以预防龋齿、治疗骨质疏松症。但是高浓度的氟化物摄入对人体的危害很大,轻则会影响牙齿和骨骼的生长发育,出现氟化骨症、氟斑牙等慢性氟中毒症状,重则引起心律不齐、恶心、呕吐等急性氟中毒。过量的氟离子对蛋白质和DNA 的合成都有抑制作用,使得免疫系统代谢紊乱,最终使机体免疫能力下降。过量的氟还会导致动物血压下降甚至贫血,影响动物的生长发育。细胞内的高氟暴露会导致线粒体氧化性损伤,降低线粒体呼吸链速率,从而导致线粒体功能紊乱。氟氯代烷,俗称氟利昂,也是上个世纪被大家广泛所利用的物质,它被用于灭火剂和空调制冷剂的制作。但是渐渐的,人们发现,氟利昂会因为光照而分解为氟自由基。所以,检测氟离子是相当必要的。目前,对氟化物的测定方法主要有离子色谱法、滴定法、分光光度法及氟离子选择电极法等。而在超分子化学的方面,有许多识别或者检测诸如氟离子等一系列对生物、环境、化工等方面有重要价值的阴离子的方法。而基于氟离子引起颜色变化的传感器,具有耗费低廉、方便检测的优点得到愈多的关注(ZL200610038254.8,ZL201510208391.0,ZL201010547945.7,ZL201410443247.0等)。由于氟离子的活泼和对人类的危害,因此它被应用于检测。当氟离子被引入到有机物时,有机物会发生许多性质的改变。我们便可以通过对这些有机物性质发生的变化来识别氟离子的含量。其中由于氟离子具有非常强的硅氧键(Si-O)切断能力,以此基础的反应型分子探针具有高度专一性。同时分子探针颜色的变化,可以裸眼观察,更好的应用于氟离子的检测。
发明内容
本发明的目的之一是提供一种苯并咪唑并苯并异喹啉酮-12-硅醚氟离子反应分子探针及其制备方法,是以1,8-萘二甲酸酐、2,3-二氨基苯酚和叔丁基二苯基氯硅烷为原料,合成对氟离子具有高选择性、特异性识别的新型氟离子分子探针。
本发明的目的通过如下技术方案实现。
一种氟离子分子探针及其制备方法,其特征在于:
(1)一种反应型氟离子分子探针,其特征是具有以下化学分子结构式:
附图1
(2)氟离子分子探针其制备方法如下:
a. 3-(叔丁基二苯基)硅基-1,2-苯二胺的制备:将2,3-二氨基苯酚和咪唑溶于二氯甲烷溶液中,向溶液中加入叔丁基二苯基氯硅烷,室温下反应48小时。浓缩反应液,柱层析分离,得浅黄色油状液体,干燥得产品;
b. 氟离子分子探针的制备:将3-(叔丁基二苯基)硅基-1,2-苯二胺和1,8-萘二甲酸酐溶于冰醋酸溶剂中,氮气保护下回流10 h,反应结束后冷却至室温,生成的黄色化合物经减压抽滤并用冰醋酸洗涤数次,黄色结晶固体;
(3)反应型氟离子分子探针的应用,其特征在于:制备的氟离子分子探针在溶剂体系中氟离子的快速检测。
本发明的另一个目的是提供一种选择性好、灵敏度高和响应速度快的检测氟离子的分子探针:在DMSO等溶剂中,进行氟离子检测测定。
本发明的优点及效果是:
(1)本发明获得高选择性氟离子分子探针,以化学性质稳定的苯并咪唑并苯并异喹啉酮-12-硅醚为分子母体,氧硅醚键为氟离子识别位点;
(2)本发明所述的探针分子原料易得,制备过程简单,条件易于控制合成产率较高,光学性能稳定;
(3)本发明获得高选择性氟离子分子探针,通过氧硅醚键可以与氟离子的发生特异性反应,使分子探针中的氧硅醚键(R-O-Si)发生断裂,转变为氧负离子(R-O-),最大吸收波长发生红移(225 nm),颜色由黄色转变为蓝色,裸眼可以清晰辨别颜色的变化,其吸收强度与氟离子的浓度具有良好的线性关系。同时表现出对氟离子的高度选择性,不受其他阴离子的干扰,并且响应速度快。该探针分子在生物医药化学、环境科学等领域都具有重要的实际应用价值。
附图说明
图1 氟离子探针分子结构式;
图2 氟离子探针的合成路线;
图3为本发明的分子探针(1×10-5 M)在加入不同浓度氟离子后紫外吸收光谱变化随浓度的关系,横坐标为波长,纵坐标为紫外吸收强度;
图4为本发明的分子探针(1×10-5 M)分别加入3当量的不同阴离子F-, Cl-, Br-, I-,HSO4 -, AcO-, H2PO4 -, ClO4 -后的紫外吸收光谱,横坐标为波长,纵坐标紫外吸收强度。
具体实施方式
附图2
实施例1:3-(叔丁基二苯基)硅基-1,2-苯二胺(中间体D1)的合成
称取0.46 g 2,3-二氨基苯酚和0.51 g 咪唑溶解于40 mL干燥的二氯甲烷溶剂中,后向溶液中加入0.96 mL叔丁基二苯基氯硅烷,室温下反应48小时。浓缩反应液,柱层析分离,得浅黄色油状液体,产率73%。核磁质谱表征如下:1H NMR (400 MHz, CDCl3) δ 7.85 (d, J= 6.5 Hz, 4H), 7.47 (dt, J = 14.0, 6.9 Hz, 6H), 6.44 (m, 2H), 6.10 (dd, J =5.8, 3.6 Hz, 1H), 3.64 (s, 4H), 1.23 (s, 9H).
分子探针D2的合成
称取中间体D1(0.79g),1,8-萘二甲酸酐(0.39)和10mL冰醋酸置于50mL圆底烧瓶中,氮气保护下回流10h。待反应完全后冷却至室温,生成的黄色色化合物经减压抽滤并用冰醋酸洗涤数次,黄色结晶固体D2,产率90%。核磁质谱表征如下:1H NMR (400 MHz, CDCl3) δ8.89 (s, 1H), 8.78 (d, J = 7.3 Hz, 1H), 8.29 (d, J = 8.2 Hz, 1H), 8.13 (dd, J= 17.5, 8.0 Hz, 2H), 7.95 – 7.73 (m, 6H), 7.41 (dt, J = 14.0, 6.9 Hz, 6H),7.11 (t, J = 8.1 Hz, 1H), 6.67 (d, J = 8.0 Hz, 1H), 1.29 (s, 9H). 13C NMR (100MHz, CDCl3) δ 160.78, 147.77, 147.51, 136.07, 135.73, 135.08, 133.59, 133.20,132.17, 131.32, 129.86, 127.83, 127.67, 127.30, 127.11, 126.99, 126.73,125.86, 123.33, 121.01, 116.02, 109.05, 26.84, 19.95. HRMS-ESI (m/z) [M+H]+计算值: 525.1998, 实测值: 525.2001.
实施例2
探针分子D2(1×10-5 M)的DMSO溶液中,测的最大吸收波长为395nm,颜色为黄色。当向溶液中滴加F-(0-30equiv),体系在波长620nm处产生了新的紫外吸收峰,最大吸收波长发生红移(225 nm)。且随F-浓度的增加,吸收强度一直在增强,直到氟离子浓度是探针浓度的30equiv时,吸收强度不再增强(如图3),溶液颜色转变为蓝色。很显然,这样的最大吸收波长的变化是由于分子探针中的氧硅醚键(R-O-Si)发生断裂,转变为氧负离子(R-O-);
实施例3
配置1×10-5 M分子探针溶液,然后向溶液中分别加入3equiv的不同阴离子F-, Cl-,Br-, I-, HSO4 -, AcO-, H2PO4 -, ClO4 -,测定在阴离子存在下,探针分子的紫外吸收光谱;
参照氟离子对探针分子的紫外吸收光谱滴定实验,本发明通过竞争阴离子实验来判定探针对氟离子的选择性,在溶液中分别加入3equiv的不同阴离子F-, Cl-, Br-, I-, HSO4 -,AcO-, H2PO4 -, ClO4 -后,紫外吸收光谱没有明显变化,在同样条件下,加入F-(3equiv)后,最大吸收波长红移225 nm,通过对紫外吸收强度的监测表明:本发明十分适合作为氟离子荧光探针(图4)。
Claims (3)
1.一种反应型氟离子分子探针(苯并咪唑并苯并异喹啉酮-12-硅醚),其特征是具有以下化学分子结构式:
2.根据权利要求1所述的氟离子分子探针,其制备方法如下:
(1)3-(叔丁基二苯基)硅基-1,2-苯二胺的制备:将2,3-二氨基苯酚和咪唑溶于二氯甲烷溶液中,后向溶液中加入叔丁基二苯基氯硅烷,室温下反应48小时,浓缩反应液,柱层析分离,得浅黄色油状液体,干燥得产品;
(2)氟离子分子探针的制备:将3-(叔丁基二苯基)硅基-1,2-苯二胺和1,8-萘二甲酸酐溶于冰醋酸溶剂中,氮气保护下回流10 h,反应结束后冷却至室温,生成的黄色化合物经减压抽滤并用冰醋酸洗涤数次,黄色结晶固体。
3.根据权利要求1所述的反应型氟离子分子探针的应用,其特征在于:制备的氟离子分子探针在溶剂体系中氟离子的快速检测。
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